Otis, MA Vacation Rentals

Explore 66 vacation rentals, homes, and villas in Otis, MA for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes, Homes with Free Parking and Best Affordable Homes, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $84 per night and featuring up to 13 bedrooms and 12 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

66 Vacation Rentals in Otis

Lakefront Otis Home w/ Stunning Views & Boats!

Otis, MA, US
2 Bedrooms • 6 Guests

Oct 22 - 25
$517 night

Escape to this light-infused retreat filled with art and nestled on 6 wooded acres. Revel in captivating views of Hayes Pond, grill on the deck, then unwind to music throughout the home. This modern 2-bedroom, 3-bath vacation rental features 3 spacious decks, outdoor dining, an office with high-speed internet, a well-stocked kitchen, and luxurious bathrooms. Swim, kayak, or take the rowboat out on the pond amid herons and beavers. Hiking, dining, skiing, and cultural attractions are also nearby! -- THE PROPERTY -- MassTaxConnect ID #C0398462250 | Hayes Pond w/ Community Boat Dock Across Street | Screened-In Deck w/ Outdoor Dining Area Bedroom Suite: King Bed | Bedroom 2: Full Bed | Living Room: King Sleeper Sofa OUTDOOR LIVING: Deck, balcony w/ lounge chairs, gas grill, rowboat w/ life jackets, kayak, bicycle w/ helmet, picnic supplies, beach towels, seasonal hot tub (Memorial Day weekend-Columbus Day weekend), fishing equipment INDOOR LIVING: 2 Smart TVs, office, vaulted ceilings, skylights, ceiling fans, soaking tub, desk, wireless sound system, telescope, books, seasonal wood-burning stove (unavailable until Spring) KITCHEN: Stove/oven, refrigerator, microwave, dishwasher, dishware/flatware, cooking basics, breakfast bar, spices, coffee maker/grinder, toaster oven, blender, ice maker, water filter GENERAL: Free WiFi, central air conditioning, towels/linens, washer/dryer, complimentary toiletries, hangers, hair dryers, trash bags/paper towels, keyless entry FAQ: Step-free entry, bedrooms on 2nd and 3rd floor, 4WD recommended PARKING: Gravel driveway (4 vehicles) -- THE LOCATION -- OUTDOOR ADVENTURES: Hayes Pond (on-site), Ashintully Gardens (3 miles), Otis State Forest (4 miles), Lake Garfield Beach (6 miles), Tyringham Cobble Park (6 miles), Otis Town Beach (7 miles), Tolland State Forest (11 miles), Sandy Beach at Laurel Lake (13 miles), Lenox Town Beach (13 miles), Keystone Arches Trailhead (16 miles), Monument Mountain Parking Lot (16 miles), Granville State Forest (17 miles) SKI RESORTS: Otis Ridge Ski Resort (4 miles), Butternut Ski Area and Tubing Center (12 miles), Ski Blandford (16 miles), Bousquet Ski Area (20 miles), Catamount Mountain Resort (22 miles), Ski Sundown (30 miles) ATTRACTIONS: Shakespeare & Company (15 miles), Chesterwood Studio (15 miles), The Mount (15 miles), Norman Rockwell Museum (16 miles), Tanglewood (17 miles), Arrowhead Museum (20 miles) NEARBY CITIES: Lee (11 miles), Great Barrington (14 miles), Stockbridge (14 miles), Lenox (15 miles) AIRPORT: Bradley International Airport (39 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: While the property features step-free entry, all of the bedrooms are located on the 2nd floor and 3rd floor and require stairs - NOTE: 4-wheel drive or all-wheel drive is recommended in the winter or during inclement weather - NOTE: The seasonal hot tub is only available Memorial Day weekend through Columbus Day weekend - NOTE: Fishing equipment is available and ice fishing can be done on the lake when safe - NOTE: The seasonal wood-burning stove is not available until Spring

Forget-Me-Not | Bold Lakefront Escape

Monterey, MA, US
4 Bedrooms • 12 Guests

Oct 12 - 14
$545 night

Welcome to Forget-Me-Not by Property Manager! Bold, modern design perched right above the shores of Lake Garfield. Forget-Me-Not is a vast, three-story Berkshires retreat with unobstructed lake views, a lofted, industrial-chic design, and plenty of ways to keep your group comfortable and entertained. The home’s moody exterior gives way to a bright, open common area where you’ll find huge windows for tons of natural light, a spacious kitchen, and vaulted ceilings over the main living room. A cozy sunroom leads to Forget-Me-Not’s large deck, which features a BBQ grill and outdoor dining table for al fresco meals overlooking the water. Soak in the hot tub, or head inside for a round of ping pong, cornhole, or heat up in the custom-built sauna. The lower floor features a second living room complete with a kitchenette and pool table, so your group will have plenty of room to spread out. With tons of privacy and unbeatable proximity to the shoreline, this contemporary lake retreat is ready to show you the best of the Berkshires. Property Manager provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips! A visit to the Berkshires in western Massachusetts is a treat for anyone looking to pair stunning rural landscapes with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods provide a wide range of outdoor activities, from rafting and fishing in the summer to skiing and tubing in the winter. Stunning at any season, this New England region is also famous for its farm-to-table food scene and local breweries. Come see for yourself! Local Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort *Home Truths:* - The dock is seasonal, it must come out of the water in fall & winter, like most docks on the lake, because the ice may permanently damage the docks. - We allow service animals at this home. If undisclosed pets are brought into the home without Property Manager’s approval there is a fine of $500 per pet. - The driveway is paved and steep, making it suitable only for 4WD/AWD vehicles, particularly in winter months. - Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request. - This home is located in the Berkshires, so you may encounter wildlife such as bugs and insects. - Guests must be 25 years or older to book this home. ​​​​​​​Parking Details: Driveway space for 2 cars to park, and parking on the other side of the road, ~6 spots total ​​​​​​​ This home comes with a pack n’ play travel crib available. A high chair can be provided upon request with at least 24hrs advanced notice. Just ask and we are happy to accommodate you and your little ones! --- The room configuration is as follows: Primary Bedroom / King bed Bedroom 2 / 2x bunk beds Bedroom 3 / King bed Bedroom 4 / King bed + 2 twin size tri-fold sleeping mats --- This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at Property Manager than the health, safety, and experience of our guests & staff. We’ve enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards. IDs will be requested for verification after booking. All bookings over 30 days require a security deposit. We report and prosecute all Credit Card Fraud. ​​​​​​​Tax #C1148950976 Licence number: C0399281930

Peaceful Cabin Close to Skiing and Hiking

Otis, MA, US
3 Bedrooms • 7 Guests

Oct 12 - 14
$260 night

An authentic Berkshire Mountains experience awaits in Otis at this 3-bedroom, 2-bathroom vacation rental by Lindal Cedar Homes. Located close to the wandering woods and waterfalls of the Otis State Forest, as well as the ski slopes of Otis Ridge and Butternut, adventure can be found surrounding the cabin any time of year! When you’re ready to spend some quality time at home, curl up in the cozy living space, admire the views from the deck, or bust out a board game for friendly competition. -- THE PROPERTY -- MassTaxConnect ID # C0396422250 | Spacious Deck | Peaceful Location | Family Friendly Bedroom 1: Queen Bed | Bedroom 2: Twin/Full Bunk Bed | Bedroom 3: Full Bed INDOOR LIVING: Smart TV, dining table, fireplace, telescope, board games, books, work desk OUTDOOR LIVING: Deck, gas grill, wooded views KITCHEN: Dishwasher, refrigerator, stove, oven, microwave, drip coffee maker, toaster, cooking basics, spices, dishware & flatware, trash bags & paper towels GENERAL: Free WiFi, central heating, complimentary toiletries, hair dryer, towels & linens, washer & dryer, iron/board FAQ: Stairs required to access, A/C: Not available, 1 Ring camera (facing driveway) PARKING: Driveway (4 vehicles) -- THE LOCATION -- HIKE & EXPLORE: Appalachian Trail (2 miles), Otis State Forest (8 miles), October Mountain State Forest (11 miles) WINTER SPORTS: Otis Ridge Ski Camp (6 miles), Butternut Ski Area and Tubing Center (18 miles), Bousquet Mountain Ski Area (18 miles), Jiminy Peak Mountain Resort (40 miles) AREA ATTRACTIONS: Naumkeag (15 miles), Berkshire Botanical Garden (16 miles), Berkshire Museum (20 miles) AIRPORT: Bradley International Airport (42 miles), Albany International Airport (61 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This property does not have air conditioning - NOTE: The property requires stairs to access - NOTE: Your safety matters. This property features an exterior Ring security camera facing the driveway. The camera is outward facing and does not look into interior spaces. The camera records video and sound when activated by motion

A-Frame Cabin w/ Furnished Deck in Becket!

Becket, MA, US
2 Bedrooms • 5 Guests

Oct 12 - 14
$199 night

Built in 1974 | Private Acreage & Scenic Surroundings | Fireside Relaxation | EV Charger Embrace a slower pace of life at this inviting 2-bedroom, 1-bath vacation rental in Becket! Set on 4 wooded acres, this rustic retro-inspired cabin offers a peaceful outdoorsy retreat with all the comforts of a work-from-home stay. Walk to the community lake or venture out to Chester-Blandford State Forest. As evening falls, settle into the hammock and ignite the gas grill for a memorable barbecue! -- THE PROPERTY -- C0443750220 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Living Room: 1 queen sleeper sofa INDOOR LIVING - Smart TV, stereo - Duraflame fireplaces (bedrooms) - Avocado organic mattresses w/ Westin Heavenly mattress pads (bedrooms), hammock - Bluetooth speaker OUTDOOR LIVING - Deck w/ seating - Private yard, hammock, games, grill KITCHEN - Refrigerator, stove/oven, microwave - Drip & Keurig coffee makers - Toaster oven, spices - Cooking basics, dishware & flatware GENERAL - Free WiFi (high speed) - Floor + table fans, ceiling fans - Baseboard heating & space heaters - Window A/C units (new 2025, living room & both bedrooms) - Linens & towels, iron/board - Please note: This property is a cabin located in a natural forest environment. Guests should expect to encounter various types of local wildlife, including bears, during their stay. FAQ - Pet fee (paid pre-trip) - Under renovations in July (no work during guest stays) ACCESSIBILITY - 2-story home, stairs required for entry - All bedrooms on 2nd floor; interior staircase is steep - Child gates (top & bottom of stairs) PARKING - Driveway (4 vehicles) -- THE LOCATION -- - Quiet area, close to ponds & hiking trails - 9 miles to Appalachian Trail & Otis Ridge - 11 miles to Chester-Blandford State Forest - 18 miles to Berkshire Museum - 19 miles to Ski Blandford - 40 miles to Bradley Int’l Airport & Albany Int’l Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $50 fee (+ fees & taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story property requires stairs to enter and interior stairs to access all bedrooms. Please be aware that the interior staircase is steep and may be challenging for some pets - Only the main floor fireplace is available for guest use. Detailed instructions are in the house book at the property - Please note: This property is a cabin located in a natural forest environment. Guests should expect to encounter various types of local wildlife, including bears, during their stay.

Monterey Home w/ Hot Tub, Pool & Game Room!

Monterey, MA, US
6 Bedrooms • 16 Guests

Oct 13 - 15
$945 night

Gather up your friends and family for the ultimate group getaway at this Monterey vacation rental! The home has nearly 4,500 square feet of interior space — including a game room, a huge sunroom, 6 bedrooms, 4 full baths, and 2 half baths — and plenty of outdoor space for everyone to enjoy. Plus, you’ll have easy access to endless outdoor adventures. Hit the slopes at Butternut Ski Area or Otis Ridge — both less than 10 miles away — take a hike on the local trails, or catch a show at Tanglewood! -- THE PROPERTY -- MassTaxConnect ID C0463041930 | Deck w/ Gas Grill | Furnished Sunroom | 8 Mi to Butternut Ski Area | 15 Mi to Tanglewood Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Bedroom 5: Queen Bed | Bedroom 6: Queen Bed | Office: Queen Sleeper Sofa | Basement Bonus Room: Queen Bed, 2 Twin Sleeper Chairs | Additional Sleeping: Full Air Mattress INDOOR LIVING: 3 Smart TVs, fireplace (wood provided), ping-pong/pool table, arcade machine, foosball table, board games, home office OUTDOOR LIVING: Pool (depth 4’-9’), hot tub, large backyard, playset, basketball hoop, pickleball net KITCHEN: Dishwasher, 6-burner gas stovetop, oven, refrigerator, microwave, cooking basics, dishware & flatware, Keurig K-Duo, percolator, coffee provided, toaster oven, beverage fridge, trash bags & paper towels GENERAL: Free WiFi, central A/C & heating, complimentary toiletries, linens & towels, in-home laundry, laundry detergent, hangers, hair dryer, keyless entry FAQ: 3 exterior security cameras (facing out) ACCESSIBILITY: 4 steps for entry, 3-story home, bedroom & full bathroom on 1st floor PARKING: Garage (2 vehicles), driveway (4 vehicles) -- THE LOCATION -- SKI RESORTS: Butternut Ski Area and Tubing Center (8 miles), Otis Ridge (9 miles), Bousquet Mountain Ski Area (19 miles), Catamount Mountain Resort (19 miles), Ski Sundown (33 miles) OUTDOOR ADVENTURES: Lake Garfield Beach (2 miles), Diane's Trail Trailhead (3 miles), Otis State Forest (8 miles), Tolland State Forest (16 miles) EXPLORE THE AREA: Berkshire Botanical Garden (13 miles), Tanglewood (15 miles), Berkshire Museum (20 miles) AIRPORTS: Bradley International Airport (43 miles), Albany International Airport (62 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This 3-story home requires 4 steps for entry. While there is a bedroom and a full bathroom on the 1st floor, additional stairs are required to access bedrooms on the 2nd floor and in the basement - NOTE: Your safety matters. This property features 3 exterior security cameras: camera 1 is on the front patio facing the driveway, camera 2 is above the garage facing the driveway, and camera 3 is on the back of the house facing the yard/pool. The cameras are outward facing and do not look into interior spaces. The cameras actively record video and sound Licence number: 21382778;C0463041930

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Monterey, MA, US
3 Bedrooms • 6 Guests

Oct 12 - 15
$395 night

Get carried away to this quaint 3-bedroom, 1-bath vacation rental in beautiful Monterey, Massachusetts. Surrounded by scenic landscapes, this cozy cottage is the perfect place to rest and recharge. Spend your days enjoying water sports from the private dock, hiking the Appalachian Trail, or taking a scenic drive to the town of Great Barrington. In the evenings, relax on the deck and fire up a feast. Immerse yourself in the natural beauty and serenity of the Berkshires at this delightful home! -- THE PROPERTY -- MassTaxConnect ID C0467761930 | Walk to Private Boat Dock | Free WiFi | Washer &amp; Dryer | Near Outdoor Recreation Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Full Bed | Additional Sleeping: Pack ‘n Play OUTDOOR LIVING: Spacious deck, screened-in porch, gas grill, dining area, 2 kayaks, beach towels, fire pit (wood not provided) INDOOR LIVING: Open layout, Smart TVs, breakfast bar, fireplace (decorative) KITCHEN: Refrigerator, microwave, stove/oven, dishwasher, cooking basics, dishware/flatware, coffee maker, trash bags/paper towels, toaster oven, Crockpot GENERAL: Linens/towels, split A/C unit (living room), complimentary toiletries, hair dryer FAQ: Single story, steps required to access PARKING: Driveway (2 vehicles) -- THE LOCATION -- SUN &amp; SAND: Lake Garfield Boat Dock (0.2 miles), Lake Garfield Beach (2 miles), Otis Town Beach (9 miles), Lenox Town Beach (13 miles), Sandy Beach at Laurel Lake (13 miles) WILD &amp; FREE: Bidwell House Trails (3 miles), Diane&#39;s Trail Trailhead (4 miles), Beartown State Forest (6 miles), Tolland State Forest (13 miles), Monument Mountain Reservation Parking (14 miles), Otis State Forest (14 miles), Granville State Forest (18 miles) MONTEREY MUST-SEES: Bidwell House Museum (3 miles), Norman Rockwell Museum (16 miles) REEL IT IN: Berkshire Rivers Fly Fishing (12 miles), Trout Pond View (13 miles), Berkshire Bass Tackle Store (15 miles) AIRPORT: Bradley International Airport (39 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you&#39;ll never want to leave. You can relax knowing that our properties will always be ready for you and that we&#39;ll answer the phone 24/7. Even better, if anything is off about your stay, we&#39;ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story property requires steps to access - NOTE: The fireplace and hot tub are unavailable for guest use Licence number: C0467761930

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

Becket, MA, US
3 Bedrooms • 8 Guests

Oct 12 - Nov 11
$528 night

Great for Families | 11 Wooded Acres | Boat Dock | Furnished Sunroom | 2 Fire Pits Whether you’re seeking thrilling outdoor adventures or quality time with loved ones, you’ll find a beautiful escape at this 3-bed, 3-bath vacation rental in the Berkshires! Sip your coffee on the patio while soaking in the pond views, then hike the Appalachian Trail or hit the slopes at Bousquet Mountain. Ready to recharge? Retreat to one of the living areas to relax by the fire. Book your Western Mass getaway! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 full bed, 1 twin bed, 1 twin sleeper sofa OUTDOOR LIVING - Patio w/ dining area - Charcoal grill - 2 fire pits - Garden - Boat dock, pond access INDOOR LIVING - 2 Smart TVs, DVD player - Wood-burning fireplace, wood-burning stove - Expansive windows, natural light - Furnished sunroom - Dining table - Board games, books KITCHEN - Refrigerator, dishwasher, electric stovetop, microwave - Keurig coffee maker (coffee provided) - Spices, toaster, blender - Cooking basics, dishware &amp; flatware GENERAL - Free WiFi - Central heating - Washer &amp; dryer, iron/board, laundry detergent - Linens, towels - Beach chairs/umbrella/towels - Hair dryer FAQ - No A/C ACCESSIBILITY - Single-story home, stairs to enter PARKING - Driveway (3 vehicles) -- THE LOCATION -- - Peaceful location near outdoor recreation: 9 lakes, watersports, renowned spas, golf courses, skiing, hiking - 6 miles to Appalachian Trail - 8 miles to Otis Ridge Ski Camp - 12 miles to October Mountain State Forest - 15 miles to Naumkeag - 17 miles to Berkshire Botanical Garden &amp; Berkshire Museum - 19 miles to Bousquet Mountain Ski Area - 20 miles to Butternut Ski Area and Tubing Center - 42 miles to Bradley Int’l Airport, 63 miles to Albany Int’l Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you&#39;ll never want to leave. You can relax knowing that our properties will always be ready for you and that we&#39;ll answer the phone 24/7. Even better, if anything is off about your stay, we&#39;ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story home requires stairs to enter - The property does not have air conditioning Licence number: C0258520220

Steepletop - Nature Lovers Paradise with Rec Room

New Marlborough, MA, US
4 Bedrooms • 8 Guests

Oct 12 - 14
$335 night

Welcome to Steepletop Lodge, a beautiful 4 bed/ 2 bath modern retreat with endless opportunities to unplug and forest bathe. A wall of windows overlooks serene woods and wetlands, and the screened porch welcomes a full three seasons of respite, situated to catch Summer breezes; with a fireplace to keep cozy in the Fall. Modern, bright, well-appointed, and stocked with games, Steepletop Lodge is a special place to reconnect with both nature and your loved ones! Following the stone path up to the front door, a spacious foyer welcomes you and seamlessly connects to the open-concept living area, with tall ceilings and flooded with natural light from a wall of windows showcasing the property’s wooded views. The living room features a woodburning stove and comfy seating, creating a cozy atmosphere within the open layout. Adjacent to the living room, find an enclosed porch with a fireplace, dining table and lounge area, perfect for enjoying nature in any weather. The kitchen is efficiently laid out and fully equipped, with an island and breakfast bar for easy meal prep and casual dining. A repurposed bowling lane serves as the dining table, inviting guests to gather for memorable meals. Three bedrooms and two baths occupy one side of the main floor. The primary bedroom offers a queen bed, a reading nook, and an ensuite bath with a walk-in shower. Large glass doors open directly onto your private deck. A second bedroom with a full bed and a twin trundle includes a convenient desk area. A full bathroom serves the bedrooms, featuring a bathtub/shower combo. A third bedroom, with twin beds, boasts a cozy reading area and charming decor. Downstairs, enjoy recreational and fitness options including a stationary bike, treadmill, ping pong table, and cozy seating area with a TV for relaxation. A fourth bedroom offers a queen bed with and convenient work space for remote work. Lastly, a laundry room completes the lower level of the home. Steepletop Lodge has been a beloved family gathering place for years, offering the perfect setting to create lasting memories with loved ones. There is a lockbox and a key inside the screened in porch. We will provide you the code during your check in process. Steepletop Lodge is approx. 2.5 hours from Boston and 3 hours from New York City. To enjoy the expansive beauty of the region, you’ll need a car to get here and get around--and the drive will be stunning! Since cell service can be inconsistent in the country, we recommend that you download the region’s online maps to your phone before your trip. We strongly advise using or renting a car that has all wheel or 4 wheel drive to access the property, especially in the colder months. *NOTE: The house does not have air conditioning; however, ceiling fans are installed in each bedroom, and additional portable fans are available throughout the home. *Please also note that two of the three first-floor bedrooms have curtains, while the third first-floor bedroom and the fourth (basement) bedroom do not have window coverings. License number: 1-454-619-424

Screened Porch & Lake Access! Tolland Haven

Tolland, MA, US
2 Bedrooms • 6 Guests

Oct 20 - 22
— night

Pets Welcome w/ Fee | Quiet Surroundings | Beach Access | 3 Mi to Granville State Forest Soak in the scenery and discover relaxation with a stay at this Tolland vacation rental! Nestled in a woodland setting, this family-friendly home boasts a cozy interior, a peaceful outdoor space, and easy access to community perks. Ready to explore? Swim or cast a line at the private Wildwood Lake, then hike the trails in Tolland State Forest. Your Massachusetts escape is ready — book today! -- THE PROPERTY -- License:C0543332970 WILDWOOD COMMUNITY AMENITIES - 5 sandy beaches (passes provided) - Hiking trails on-site - Pickleball &amp; tennis courts, clubhouse - Picnic areas - Laundry area (w/ addt’l fee) HOME FEATURES - Lake access &amp; view - Spacious backyard - Screened porch w/ dining area - Flat-screen TVs - Board games KITCHEN - Stove/oven, refrigerator, microwave - Cooking basics, dishware/flatware - Keurig drip &amp; pod coffee maker (starter coffee provided) - Toaster, blender, spices ACCESSIBILITY - Single-story home, 5 steps to enter PARKING - Driveway (4 vehicles) -- THE LOCATION -- - Lakefront community on-site: fishing, swimming, hiking - 9 miles to Tolland State Forest - 14 miles to Otis Ridge - 26 miles to The New England Air Museum - 29 miles to Naumkeag -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly with $50 fee (+ fees &amp; taxes, 2 pets max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - Basement access is not available for guest use Licence number: C0543332970

Cordelia | Amazing Backyard, 10mins from Stockbridge!

Lee, MA, US
5 Bedrooms • 12 Guests

Oct 19 - 21
$276 night

Cordelia is a cottage in the best sense of the word: chic where it counts, unfussy everywhere else, and built around outdoor spaces that do most of the work. The backyard is the argument — a brick patio with a dining table set for long dinners, a firepit for after, a hammock for the hour nobody wants to account for, and enough lawn for a round of cornhole that somehow turns into four. Inside, the house keeps its character. The front living room pairs a fireplace with a TV for the evenings that end early. There’s a formal dining room for the meal somebody’s been planning since the group chat started, and a country kitchen with antique pieces that give it a lived-in warmth most rentals spend a fortune trying to fake. Five bedrooms mean everyone gets to spread out, and the clawfoot tub upstairs is the reward at the end of a long day outside — the kind of soak that makes you understand why people keep coming back to New England in the shoulder season. The Berkshires are less a destination than a whole county’s worth of them, which means the week shapes itself around whatever you’re after. World-class art sits at both ends of the region — MASS MoCA in the old mill buildings of North Adams and the Clark Art Institute in Williamstown to the north, the Norman Rockwell Museum in Stockbridge to the south. Tanglewood draws crowds to Lenox all summer, Jacob’s Pillow brings dance to Becket, and Mount Greylock, Monument Mountain, and Bash Bish Falls cover the hiking from a state high point down to a waterfall in the far southwest corner. Great Barrington and the surrounding villages handle the browsing, the bookshops, and the long, unhurried dinners. It’s more than any one visit can hold, which tends to be the point. Property Manager provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips! Visiting the Berkshires is a must for anyone looking to pair a gorgeous natural landscape with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods here makes it easy to enjoy a wide range of outdoor activities, from rafting and fishing to ziplining and hiking. Stunning in any season, this region is famous for its food scene, which values local ingredients, and you’ll find many farm-to-table establishments in the southern areas. Explore classic New England architecture, a growing array of performing arts, and dozens of towns and trails. The Berkshires are waiting with variety and beauty you won’t find anywhere else. Local Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort Home Truths: - This home allows pets for a fee. If undisclosed pets are brought into the home without Property Manager’s approval there is a fine of $500 per pet. - This home does not have AC. - Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request. - This home is located in the Berkshires, so you may encounter wildlife such as bugs and insects. ​​​​​​​This home comes with a pack n’ play travel crib and a high chair available. ​​​​​​​--- The room configuration is as follows: Primary Bedroom: King bed w/ ensuite Bedroom 2: Queen bed Bedroom 3: Queen bed Bedroom 4: King bed Bedroom 5: Queen bed --- This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at Property Manager than the health, safety, and experience of our guests & staff. We’ve enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards. IDs will be requested for verification after booking. All bookings over 30 days require a security deposit. We report and prosecute all Credit Card Fraud. Licence number: C0399231500

Modern Berkshires Farmhouse w/ Porch, Fireplace & Views | Beaver Creek

Stockbridge, VT, US
4 Bedrooms • 8 Guests

Oct 25 - 27
$310 night

Welcome to Beaver Creek by Property Manager! Tucked amid the rolling hills and vibrant forests of Stockbridge, Beaver Creek is a storybook escape where New England charm meets modern comfort. This picturesque retreat sits surrounded by lush gardens and autumn-kissed scenery, offering a front-row seat to the Berkshires’ beauty—just minutes from the serene Stockbridge Bowl, historic Main Street, and cultural icons like Tanglewood and the Norman Rockwell Museum. Step inside to discover bright, inviting interiors that balance timeless elegance with relaxed comfort. The living room, wrapped in soft whites and natural light, centers around a cozy wood-burning fireplace—perfect for gathering after a day exploring nearby trails or art galleries. Adjacent, the dining room seats eight for memorable meals, while the fully equipped kitchen makes entertaining easy with its modern finishes and sunny window views. Four serene bedrooms promise peaceful rest, including two spacious king suites and a cheerful bunk room ideal for kids or friends. The primary suite offers a spa-like ensuite bath with a soaking tub and walk-in shower, while an additional full bathroom and half bath ensure comfort for all. Outdoors, you’ll find every reason to linger—from morning coffee on the covered porch to sunset barbecues in the crisp mountain air. The patio features a grill, picnic table, and lounge seating for six, surrounded by manicured landscaping and views that shift beautifully with the seasons. Whether you’re leaf-peeping in the fall, skiing at nearby resorts in the winter, or soaking in lake breezes come summer, Beaver Creek invites you to experience the best of the Berkshires in style and serenity. Property Manager provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. Visiting the Berkshires is a must for anyone looking to pair a gorgeous natural landscape with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods here makes it easy to enjoy a wide range of outdoor activities, from rafting and fishing to ziplining and hiking. Stunning in any season, this region is famous for its food scene, which values local ingredients, and you’ll find many farm-to-table establishments in the southern areas. Explore classic New England architecture, a growing array of performing arts, and dozens of towns and trails. The Berkshires are waiting with variety and beauty you won’t find anywhere else. Local Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort. Visit High Lawn Farm, a beloved local creamery known for its farm-fresh ice cream, handcrafted cheeses, and artisanal dairy made right in the Berkshires. Home Truths: - Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without Property Manager’s approval there is a fine of $500 per pet. - The property uses well water, which is safe for consumption and daily use. - The home operates on a septic system, so please avoid flushing anything other than toilet paper. - A static lock code provides access to both the main gate and the house. - Firewood is not provided; please bring your own if you plan to use the fireplace or fire pit. - This home is located on a working farm, so guests may notice occasional farm activity such as tractors, planting, and harvesting. - Local wildlife may be present in the area, so please enjoy with care and keep food securely stored. - A pack ’n play and high chair are available for guest use. Parking Details: - Parking is available in the driveway for up to 6 vehicles; the garage is not accessible, but there are no neighborhood parking restrictions. All bookings over 30 days require a security deposit to be charged after booking. This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at Property Manager than the health, safety, and experience of our guests & staff. We’ve enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards. IDs will be requested for verification after booking. All bookings over 28 days require a security deposit. We report and prosecute all Credit Card Fraud. Licence number: C0533330700

Tranquil 3 BR Stockbridge House w/ Private Deck!

Stockbridge, MA, US
3 Bedrooms • 6 Guests

Oct 14 - 17
— night

Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house! Boasting a private deck, fireplace, in-unit laundry, and 114 acres of property to explore, this home-away-from-home can’t be beat! When you aren’t enjoying the stunning exterior space on the expansive deck or spotting wildlife like owls, foxes, and deer, venture off-site for skiing at Butternut Basin or swimming at Stockbridge Bowl. Whether snowy or sunny, endless adventures await! -- THE PROPERTY -- 1,600 Sq Ft | Pets Welcome | Free WiFi Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat, complete with tranquil privacy and modern comforts. Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds OUTDOOR LIVING: Gas grill, 114 acres of hiking trails KITCHEN: Fully equipped, drip coffee maker, Keurig coffee maker, toaster, electric pancake skillet, ice cube maker, cafe table INDOOR LIVING: 2 TVs, HD TV, fireplace, dining table, Apple Mac-Mini computer, cell phone charging station GENERAL: Washer &amp; dryer, towels, linens, complimentary toiletries, central air conditioning/heat, keyless entry, pet fee (paid pre-trip) SUITABILITY: Stairs required PARKING: Driveway (2 vehicles), detached garage (1 vehicle), outdoor area (1 vehicle) -- THE LOCATION -- STOCKBRIDGE BOWL (4.0 miles): Stockbridge Town Beach, BSO Beach, Stockbridge Bowl Boat Ramp, boating, swimming, fishing, kayaking, paddle boarding, canoeing HIKING: 114 acres on-site, Stevens Glen Trail Head (4.8 miles), Monument Mountain Reservation (4.8 miles), Olivia&#39;s Overlook (5.5 miles), Brothers Trail (6.0 miles), Burbank Trail (6.2 miles), Parsons Marsh Reserve (6.5 miles), Appalachian Trail (12.1 miles) LOCAL ATTRACTIONS: Norman Rockwell Museum (1.4 miles), Orleton Farm (3.7 miles), Tanglewood (5.6 miles), Koussevitzky Music Shed (5.8 miles), Seiji Ozawa Hall (6.7 miles), Frelinghuysen Morris House &amp; Studio (6.7 miles), The Playhouse (6.9 miles), Ventfort Hall Mansion and Gilded Age (7.4 miles), The Mount, Edith Wharton&#39;s Home (7.5 miles) SKIING: Ski Butternut (9.9 miles), Catamount Mountain Resort (14.6 miles), Jiminy Peak Mountain Resort (25.8 miles) AIRPORT: Albany International Airport (48.0 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you&#39;ll never want to leave. You can relax knowing that our properties will always be ready for you and that we&#39;ll answer the phone 24/7. Even better, if anything is off about your stay, we&#39;ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - Massachusetts Tax ID: C0214960870 - No smoking - Pet friendly w/ $75 fee (+ fees &amp; taxes, maximum 3 pets allowed) - No events, parties, or gatherings of more than 6 people - No fireworks allowed on the property - Garage is unavailable during winter months (11/15-4/15) - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Access to the home requires stairs Licence number: C0214960870

Historic Huntington Home - Walk to Westfield River

Huntington, MA, US
3 Bedrooms • 6 Guests

Oct 12 - 14
$271 night

Experience historic charm and colonial beauty when you cross the threshold into this 3-bedroom, 2-bath Huntington vacation rental. This house, built in 1789, still boasts many of the original furnishings, providing a memorable New England retreat that you won&#39;t find elsewhere! Enjoy modern amenities, too, including air conditioning, plush beds, and a DVD player with a large movie collection! You will be right across from a swimming hole, surrounded by forests, and near the Appalachian Trail! -- THE PROPERTY -- MassTaxConnect ID #: C0295701430 | 3,000 Sq Ft | Free WiFi Leave it to Massachusetts to provide the most charming historic home, the perfect spot for families or friend groups looking for an antique feel combined with easy access to nature. Bedroom 1 (Chester Room): Queen Bed | Bedroom 2 (Skyline Road): Full Bed | Bedroom 3 (Back Room): 2 Twin Beds | Living Room: Sleeper Sofa OUTDOOR LIVING: Large backyard, wooded views, river access MODERN AMENITIES: TV, DVD player, books, ceiling fans, 6-person dining table HISTORIC TOUCHES: Original wood flooring, wood-burning fireplaces, antique furniture, clawfoot tub KITCHEN: Fully equipped, tea kettle, toaster, toaster oven, Keurig coffee maker, dishware/flatware GENERAL: Washer &amp; dryer, linens, towels, beach towels, hair dryer, A/C in all bedrooms FAQ: Stairs required for access PARKING: Driveway (5 vehicles) -- THE LOCATION -- EXPLORE NATURE: Sanderson Brook Waterfall (2.8 miles), Goldmine Brook Falls (3.0 miles), C.M. Gardner State Park (4.6 miles), Chester Becket Railroad Trailhead (5.8 miles), Huntington State Forest (7.4 miles), Becket Quarry (9.3 miles), Appalachian Trail (17.1 miles), Otis Ridge (18.2 miles), October Mountain State Forest (23.6 miles) LOCAL FARE: Comfort Kitchen &amp; Bar (2.0 miles), The Rapids Bar &amp; Grill (5.1 miles), Chester Common Table (5.6 miles), Russell Inn (5.7 miles), Red Lion Inn (26.4 miles) MUSIC: The Iron Horse Music Hall (17.8 miles), Pearl Street - Northampton (18.0 miles), Tanglewood - Lenox (27.3 miles) AIRPORT: Bradley International Airport (31.8 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you&#39;ll never want to leave. You can relax knowing that our properties will always be ready for you and that we&#39;ll answer the phone 24/7. Even better, if anything is off about your stay, we&#39;ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs and may be difficult for guests with limited mobility Licence number: C0295701430;C0295701430

Woodland Zen | Modern Design + Patio

Stockbridge, MA, US
3 Bedrooms • 6 Guests

Oct 12 - 14
$185 night

Introducing Woodland Zen: where modern luxury meets secluded tranquility in the heart of the Berkshires. This sleek, contemporary escape will take your breath away from the moment you arrive. Surrounded by lush greenery, its modern exterior is a unique contrast with the natural landscape. Step onto your spacious deck, complete with comfortable seating and a BBQ grill, and immerse yourself in the serenity of the surrounding woodland. Floor-to-ceiling windows flood the living spaces with natural light, offering stunning views of the picturesque landscape. The bright, open living room features a large fireplace, plush seating, and a TV. Need more space? Discover a second sitting area with an additional sofa and TV. Entertain in style in the sleek dining area, nestled next to the windows and overlooking the patio. With seating for 8, it’s perfect for gatherings. Plus, there’s another dining table in the adjacent sunroom with seating for 6. Cooking is a breeze in the fully equipped kitchen, boasting stainless steel appliances, a gas range, and ample counter space. Additional barstool seating ensures everyone has a place to gather. Retreat to one of three comfortable bedrooms, each featuring a plush queen bed. The primary suite boasts an attached ensuite bathroom and access to the patio, perfect for enjoying your morning coffee in peace. Conveniently located just 10 minutes from Great Barrington, you’ll have easy access to dining, shopping, wine tasting, and outdoor adventures. With in-home laundry and parking, Woodland Zen offers the ultimate blend of luxury, privacy, and convenience for your Berkshire getaway. Property Manager provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips! A visit to the Berkshires in western Massachusetts is a treat for anyone looking to pair stunning rural landscapes with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods provide a wide range of outdoor activities, from rafting and fishing in the summer to skiing and tubing in the winter. Stunning at any season, this New England region is also famous for its farm-to-table food scene and local breweries. Come see for yourself! Local Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort Home Truths: - Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request. - Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without Property Manager’s approval, there is a fine of $500 per pet. Parking Details: - Parking is available onsite for 4 vehicles in the carport and driveway. - No street parking is permitted. --- The room configuration is as follows: Primary Bedroom / Queen bed w/ ensuite Bedroom 2 / Queen bed Bedroom 3 / Queen bed --- This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at Property Manager than the health, safety, and experience of our guests & staff. We’ve enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards. IDs will be requested for verification after booking. All bookings over 28 days require a security deposit. We report and prosecute all Credit Card Fraud. Licence number: C0485752830

River Cottage - Riverfront Home in Walkable Community

Great Barrington, MA, US
3 Bedrooms • 6 Guests

Oct 12 - 14
$502 night

Welcome to River Cottage, a beautifully renovated 3-bedroom, 2-bathroom riverfront gem in the heart of Great Barrington. Located along the scenic Housatonic River, this enchanting home offers the serenity of country living with the added benefit of being within walking distance to all the amenities of a vibrant, walkable community. River Cottage is just a short stroll away from local favorites like Prairie Whale, charming shops, and the bustling Farmer’s Market. River Cottage boasts a pristine, completely renovated interior with gorgeous finishes throughout. The open-concept living and dining rooms flow effortlessly into a chef’s kitchen, complete with a walk-in country pantry. Upstairs, the primary bedroom features a king bed, complemented by two guest bedrooms—one with a queen bed and the other with another king bed. Two beautifully appointed bathrooms ensure privacy and convenience for all guests. Enjoy your morning coffee on the charming, wrapping front porch or host a delightful al fresco dinner in the backyard’s outdoor dining area. The fenced backyard extends to the water’s edge, offering stunning river views. Entertain guests on the back deck, relax in one of the many seating areas, or enjoy a cozy fire in the riverfront fire pit. River Cottage is the epitome of a country escape, providing a perfect blend of tranquility and convenience. Whether you’re seeking a weekend getaway or a longer retreat, this idyllic home offers everything you need to relax, entertain, and enjoy the best of Great Barrington. Come experience the magic of River Cottage—where country living meets urban walkability in the most delightful way. Guests at River Cottage have access to the entire home, the front porch and yard, and backyard with patio, herb garden, fire pit, and river view. River Cottage is approx 2.5 hours from Boston and just under 3 hours from New York City. You’ll need a car to get here and get around the Berkshires, but downtown Great Barrington is just a short walk away! The house has moderate cell service, but the surrounding areas are full of cellular dead zones. We recommend downloading the region’s online maps to your device prior to your arrival or any day tripping you do while you’re here. Cooling: The home features window A/C units in both queen bedrooms, and mini-split units in the king bedroom and dining room. License number: 1-286-847-264

Meadow Top Cottage: Countryside Cottage on 72 Acres

New Marlborough, MA, US
3 Bedrooms • 6 Guests

Oct 12 - 14
$315 night

Meadow Top Cottage is charming and cozy 3-bed, 2-bath cottage in the quiet hamlet of Mill River, MA. The 72-acre property offers exquisite views of the Litchfield hills, an outdoor patio and a fire pit nestled in a pine grove. The town’s charms include: candlelit dinners at The Old Inn on the Green, provisions at the Mill River General Store, brunch at the Southfield Store, swimming at Umpachene Falls, and hikes both on and off the property. Winter skiers are also within 15-20 minutes of Butternut and Catamount. With natural wood finishes throughout, Meadow Top Cottage exudes a quaint and homely charm that makes it a true countryside haven. The cozy living room, complete with a brick fireplace and TV, is perfect for relaxing evenings. The fully equipped kitchen, featuring flatware, silverware, cookware, and appliances, caters to both seasoned chefs and casual cooks alike. The cottage features three inviting bedrooms (1 Queen, 1 Full, and 2 Twins), ensuring a restful night’s sleep for all guests. Two well-appointed bathrooms provide modern convenience and comfort. Step outside to discover the true essence of country living. Wander through the mature gardens before settling on the outdoor patio. This space is perfect for alfresco dining or simply relaxing while soaking in the serene landscape. Enjoy a barbecue on the grill or gather around the pine grove fire pit for cozy evenings under the stars. We strive to make your stay as easy and enjoyable as possible by providing fresh linens, fluffy towels, and toiletries. The kitchen is equipped with basic essentials including a coffee maker and grinder, a full set of pots and pans, plates, and cutlery. Stay connected with WiFi by Spectrum and stream your favorite media on the Smart TV. Escape the hustle and bustle of everyday life and immerse yourself in the tranquility of Meadow Top Cottage. Whether you’re looking to relax, explore, or create unforgettable memories with loved ones, this charming country retreat is the perfect destination. Book your stay today and experience the magic of Meadow Top Cottage. Guests have exclusive access to the cottage and a private outdoor space with grill, table and chairs; access to the larger 56-acre estate is shared, which includes lush grounds and a rolling landscape. The pool and hot tub on property are not included in the cottage amenities. Meadow Top Cottage is under 3 hours from Boston and 3 hours from NYC. You’ll need a car to get here and to get around. The house has an internet connection and moderate cell service with AT&T, T-Mobile and Verizon. The Berkshires is full of cellular dead zones, so we recommend downloading the region’s online maps to your device prior to arrival or any day while you’re here at the cottage. The cottage has a shared driveway, so please make sure you do not park in the circle of the driveway. Either pull into one of the spots or use the garage. Thank you! A/C: The house has 2 window AC units for cooling and does not have central AC. License number: C0496912030

Great Barrington Lakeside Getaway w/ Kayak & Grill

Great Barrington, MA, US
4 Bedrooms • 10 Guests

Oct 19 - 22
$395 night

Enjoy stunning water views and lakeside fun at this 4-bedroom + den, 4-bath vacation rental in the Berkshires. A mixture of older appliances and modern amenities, like 2 large decks and a kayak, makes this home a bright and comfortable nature retreat. Enjoy eclectic shops, galleries, and farm-to-table restaurants only a few miles away in the vibrant town of Great Barrington. Check out attractions like Tanglewood, Butternut Basin, Jacob&#39;s Pillow, museums, and bike trails on the Appalachian Trail. -- THE PROPERTY -- Permit: C0462781130 | 6 Mi to Skiing | Fireplace | Hiking, Skating, Ice Fishing, &amp; Swimming (On-Site) | Fast EV Charger Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds | Bedroom 4: Full Bed | Den: Full Futon OUTDOOR LIVING: Gas grill, kayak, wraparound deck, lake w/ spacious dock (walking distance), walking trails nearby INDOOR LIVING: Board games, en-suite bath, flat-screen TV, jetted tub, fireplace KITCHEN: Dishwasher, microwave, stove/oven, dishware &amp; flatware, cooking basics, toaster oven GENERAL: Linens, dryer, hair dryer, iron/board, complimentary toiletries, keyless entry, laundry detergent, towels, trash bags/paper towels, free WiFi, central heating, central air conditioning (older unit) ACCESSIBILITY: 2-story home, exterior staircase required, interior steps required to access bedrooms FAQ: Quiet hours (8:00 PM-8:00 AM), 152 steps required to reach lake (waiver may be required), gun club nearby (may occasionally hear gun shots) PARKING: Driveway (4 vehicles) -- THE LOCATION -- WINTER FUN: Butternut Ski Area and Tubing Center (6 miles), Catamount Mountain Resort (10 miles), Bousquet Mountain Ski Area (15 miles), Jiminy Peak Mountain Resort (29 miles) SUMMER SUN: Housatonic Flats Reserve (5 miles), Fountain Pond State Park (5 miles), Monument Mountain (5 miles), East Mountain State Forest (7 miles), Edith Wharton Park (13 miles), Appalachian Trail (14 miles) THINGS TO DO: Berkshire South Regional Community Center (5 miles), Norman Rockwell Museum (5 miles), Berkshire Botanical Garden (6 miles), Lee Premium Outlets (14 miles), Canyon Ranch Lenox (14 miles) AIRPORTS: Albany International Airport (51 miles), Bradley International Airport (76 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you&#39;ll never want to leave. You can relax knowing that our properties will always be ready for you and that we&#39;ll answer the phone 24/7. Even better, if anything is off about your stay, we&#39;ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This charming property is on the lake and is the perfect place to relax. This is an older property with stunning lake views - NOTE: This 2-story home requires using an exterior staircase to enter; additional interior steps are required to access the bedrooms - NOTE: Please observe quiet hours from 8:00 PM to 8:00 AM - NOTE: There are 152 steps on a long wooden staircase required to reach the dock at the lake. These stairs are not shoveled or cleared of ice in the winter. A waiver may be required before using the stairs - NOTE: There is a gun club down the road and occasionally, usually on a Sunday, you may hear gunshots - NOTE: This home offers old-fashioned appliances and quirks. While not a luxury property, it offers all the essentials for a pleasant stay!

Walk to Dining: Downtown Lenox Guest House!

Lenox, MA, US
3 Bedrooms • 6 Guests

Oct 12 - 15
$364 night

Steps to Main Street | 2 Mi to Tanglewood | Private Yard w/ Grill This Lenox vacation rental places you in the heart of the Berkshires! Steps from shops and restaurants and minutes from Tanglewood, you’ll enjoy easy access to world-class arts, culture, and outdoor adventure. The 3-bedroom, 2.5-bath home is also conveniently located within a short drive of the Appalachian Trail and ski resorts. After exploring, relax with a backyard barbecue or unwind inside with all the comforts of home. -- THE PROPERTY -- C0514291520 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 full bed STEP OUTSIDE - Private yard w/ gas grill - Front yard w/ garden INDOOR LIVING - Hardwood flooring - Smart TVs - Natural sunlight KITCHEN - Refrigerator, stove/oven, dishwasher, microwave - Drip coffee maker, toaster oven - Cooking basics GENERAL - Free WiFi - Central heating &amp; A/C - Linens &amp; towels, complimentary toiletries FAQ - Quiet hours (10:00 PM-8:00 AM) ACCESSIBILITY - 2-story home, 3 steps to enter PARKING - Designated parking spaces (2 vehicles) - Additional vehicles must be parked in public parking (not at the nearby inn) -- THE LOCATION -- - Close to hiking trails, skiing resorts &amp; golf courses - 2 miles to The Mount, Edith Wharton&#39;s Home - 5 miles to Bousquet Ski Area - 10 miles to Fountain Pond State Park - 13 miles to Appalachian Trail - 51 miles to Albany International Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you&#39;ll never want to leave. You can relax knowing that our properties will always be ready for you and that we&#39;ll answer the phone 24/7. Even better, if anything is off about your stay, we&#39;ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Please observe quiet hours from 10:00 PM and 8:00 AM ADDITIONAL INFORMATION - This 2-story home requires 3 steps to enter Licence number: C0020201520;C0514291520;LENOX SHORT TERM RENTAL REGISTRATION

52-Acre Berkshires Farmhouse • Fire Pit, Outdoor Dining + Trails | Copper Kettle Farm

Sheffield, MA, US
4 Bedrooms • 14 Guests

Oct 12 - 14
$424 night

Welcome to Copper Kettle Farm by Property Manager, a newly renovated farmhouse retreat set across 52 sweeping acres in southern Berkshire County. Designed for restorative escapes and joyful gatherings, this charming home blends Colonial-era character with fresh, modern comforts—creating a space that feels both timeless and thoughtfully updated. Inside, the farmhouse opens into bright, inviting living spaces made for connection. A brand-new kitchen anchors the home, fully stocked and outfitted with new appliances, perfect for shared meals and lingering conversations. Multiple gathering areas allow groups to spread out with ease, including a quiet play space for children and a cozy living room with a sofa and doors that fully close—ideal as an additional private sleeping or lounging area. Throughout the home, new beds, bedding, and updated bathrooms ensure comfort at every turn, while zoned heating and air conditioning, WiFi, Roku TV access, and a new washer and dryer add everyday convenience. With four spacious bedrooms and 2.5 bathrooms, Copper Kettle Farm is designed to welcome families and larger groups alike, offering both togetherness and room to unwind. Step outside, and the landscape truly steals the show. Rolling farmland stretches toward the Appalachian Mountains, creating a serene backdrop for morning coffee or golden-hour gatherings. Adirondack chairs, a grill, a fire pit, and an outdoor dining set invite you to linger outdoors, soaking in the views and the quiet rhythm of the countryside. The property also offers direct access to highly rated hiking trails and cycling routes, making it easy to explore the surrounding natural beauty right from your doorstep. Perfectly positioned, the farm serves as a central home base for discovering the best of the Berkshires and nearby northwest Connecticut. Spend your days exploring the charm of Great Barrington, Stockbridge, Lenox, and Lee, or venture to Salisbury, Lakeville, Cornwall, and Kent just over the state line. The home is especially well-suited for visits to local private schools—including Berkshire, Hotchkiss, and Salisbury, all within 20 minutes—and for winter escapes to Catamount and Butternut ski areas. Whether you’re gathering with family, reconnecting with friends, or simply seeking a peaceful countryside reset, Copper Kettle Farm offers space, scenery, and comfort in equal measure—an unforgettable setting for making memories that last. Property Manager provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips. A visit to the Berkshires in western Massachusetts is a treat for anyone looking to pair stunning rural landscapes with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods provides a wide range of outdoor activities, from rafting and fishing in the summer to skiing and tubing in the winter. Stunning at any season, this New England region is also famous for its farm-to-table food scene and local breweries. Come see for yourself! Local Attractions: Beartown State Forest, East Mountain State Forest, Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort Home Truths: - Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without Property Manager’s approval, there is a fine of $500 per pet. - Please note that the fireplaces are non-operational and are for decorative purposes only. - A property manager lives in a separate building sharing this home’s driveway. Parking Details: - Parking is available for 8 vehicles. This home comes with a pack n’ play travel crib and a high chair available. --- The room configuration is as follows: Primary Bedroom / King bed Bedroom 2 / Queen bed Bedroom 3 / Queen bed Bedroom 4 / 2 full-over-full bunk beds, 1 XL twin over XL twin bunk bed --- This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. We report and prosecute all Credit Card Fraud. Licence number: C0549192670

Historic Farmhouse Near Mountains & Colleges!

Westfield, MA, US
4 Bedrooms • 8 Guests

Oct 18 - 20
$235 night

Situated on 7 acres of sprawling land, this restored vintage farmhouse has all the warmth and charm of a historic house while offering the modern comforts of home. Complete with an upscale interior, ample outdoor space, and views of local mountains, this 4-bedroom, 2-bath vacation rental will immerse you in the serenity of countryside living while conveniently located by Easthampton, Northampton, and 5 area colleges. This retreat also offers access to state parks, museums, and family activities! -- THE PROPERTY -- C0491833290 | Sunroom | Private Outdoor Dining Area | ~5 Mi to Hampton Ponds State Park Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed OUTDOOR LIVING: Covered porch w/ ceiling fan &amp; lounge space, back patio w/ dining area, gas grill, large yard area, garden, barn (decorative only) KITCHEN: Fridge, stove/oven, dishwasher, microwave, fully stocked kitchen, spices, toaster, kettle, dishware/flatware, paper towels/trash bags, complete coffee bar w/ Keurig (variety of flavored &amp; organic K-cups, sugars/sweeteners, syrups provided), tea kettle (assorted black &amp; herbal teas provided) INDOOR LIVING: Smart TVs, multiple living areas, dedicated dining room, office/vanity space, board games, pellet stove (decorative only) GENERAL: Free WiFi, linens, towels, washer &amp; dryer, central air conditioning &amp; heating, complimentary toiletries, hair dryer, iron/board, keyless entry ACCESSIBILITY: Stairs required to access, multi-level home, bedroom &amp; bathroom on main level PARKING: Driveway (3 vehicles) -- THE LOCATION -- OUTDOORS: Allen Disc Golf Course (0.1 miles), Hampton Ponds State Park (5 miles), Stanley Park (7 miles), Robinson State Park (12 miles), Connecticut Riverwalk and Bikeway (14 miles), Van Horn Park (15 miles), Chicopee Memorial State Park (18 miles) AREA UNIVERSITIES: Westfield State University (8 miles), Smith College (13 miles), Mount Holyoke College (14 miles), Amherst College (25 miles), UMass Amherst (25 miles) HISTORIC SITES: Naismith Memorial Basketball Hall of Fame (16 miles), Forest Park Heights Historic District (16 miles), Springfield Museums (16 miles), Springfield Armory National Historic Site (16 miles) THINGS TO SEE + DO: Amelia Park Children&#39;s Museum (6 miles), Children&#39;s Museum at Holyoke (10 miles), Eastern States Exposition (13 miles), Dr. Seuss National Memorial Sculpture Garden (16 miles), Six Flags New England (17 miles), Zoo in Forest Park and Education Center (19 miles) AIRPORT: Bradley International Airport (23 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This multi-level property requires several exterior stairs and 1 interior step to access the main level. Although there is a bedroom on the main level, interior stairs are required to access all other bedrooms on the upper level - NOTE: The pellet stove and barn are not available for guest use

Water-View Home in the Berkshires

Sheffield, MA, US
3 Bedrooms • 6 Guests

Oct 17 - 19
$315 night

2,262 Sq Ft | Ping-Pong Table | Nestled on Mill Pond | &lt; 6 Mi to Dwtn Great Barrington Take a break from the city and book this Sheffield vacation rental in the Berkshires! The 3-bed, 2-bath house boasts a retro interior, a full kitchen, a wood-burning fireplace, and stellar pond and fall color views! Conveniently located near Catamount Mountain Resort, Butternut Ski Area, the Appalachian Trail, and more, this home is the perfect choice for those seeking both adventures and relaxation! -- THE PROPERTY -- C0383872670 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 full bed - Bedroom 3: Twin Bunk Bed INDOOR LIVING - Smart TV w/ cable, dining table - Wood-burning fireplace - Board games, books - Dining table, ping-pong table - En-suite bathroom, natural light OUTDOOR LIVING - Waterfront, Solo Stove Yukon fire pit - Private yard, enclosed porch - Small covered deck, dining set KITCHEN - Refrigerator, stove/oven, dishwasher - Dishware/flatware, cooking basics, spices - Drip coffee maker, microwave, toaster GENERAL - Free WiFi - Central heating, window A/C units, ceiling fans - Linens/towels, washer/dryer - Complimentary toiletries, hair dryer FAQ - Exterior security camera (facing out) ACCESSIBILITY - Single-story home, 2 steps to enter PARKING - Garage (2 vehicles) - Driveway (2 vehicles) -- THE LOCATION -- - Near waterfalls, hiking &amp; skiing - 4 miles to Appalachian Trail - 7 miles to Catamount Mountain Resort - 9 miles to Mill River Historic District - 10 miles to Butternut Ski Area and Tubing Center - 49 miles to Bradley International Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you&#39;ll never want to leave. You can relax knowing that our properties will always be ready for you and that we&#39;ll answer the phone 24/7. Even better, if anything is off about your stay, we&#39;ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - Your safety matters. This property features 1 exterior security camera located on the garage, facing outward toward the driveway. It does not look into any interior spaces. The camera records video and sound when activated by motion. It will record when it first senses motion and 30 seconds after the last motion is detected - This single-story home requires 2 steps to enter

Bow & Beam | Timber-Frame Retreat + Chef’s Kitchen + Game Room | 3.5 Acres + Trails

Sheffield, MA, US
4 Bedrooms • 10 Guests

Oct 12 - 14
$200 night

The drive ends at a wide green lawn, and then the house: shingled, gabled, and quietly substantial, with woods drawing a line behind it and the southern Berkshires rolling out beyond. Bow & Beam is the kind of place that makes a group exhale on arrival. Bow & Beam is a spacious timber-frame retreat on 3.5 wooded acres in Sheffield, designed for families and groups who want a beautiful place to spend time together, with plenty of room to spread out when they don’t. Four bedrooms and four full baths, a huge wraparound deck, a wood-stove, a kitchen built for serious cooking, and a downstairs game room make this a house that works as well for a long summer week as it does for a ski weekend or a gathering of friends and family. Inside, the frame does the talking. Heavy timber posts and beams run overhead through the great room, warm against white walls and deep red accents, with a wood-stove anchoring one end and a piano waiting nearby for whoever’s brave enough after dinner. The living room flows naturally to a dining table for eight, and then into to a kitchen designed for people who actually cook. There’s a professional range beneath a statement hood, a long butcher-block island, and a level of equipment that surprises even confident cooks --- stand mixer, blender, toaster, coffeemaker, five sets of pots and pans, a knife block, mixing bowls, a second dishwasher, and a mini fridge, plus a bar area with its own beverage fridge. Big holiday meals happen here without anyone tripping over anyone. The sleeping spaces are spread thoughtfully across the house, with a primary suite upstairs featuring a king bed and ensuite bath with dual sinks, a shower, and a tub, and just outside the door a second full bath --- also dual sinks --- serves the rest of the floor. A queen room and a twin room fill out the upstairs, and a fourth bedroom with a queen sits on the main level near its own full bath, which is the arrangement grandparents and light sleepers always hope for. All told, four bedrooms sleep ten, with a den for reading and an office for the calls that follow you on vacation. Downstairs is where the trip loosens up. The game room is set for a full evening — foosball, ping pong, air hockey — with a laundry room and another full bath on the same level, so wet boots and beach towels never have to make it upstairs. Then there’s the deck, which wraps the house and effectively doubles it. One long table seats twelve under open sky, a smaller four-top sits off to the side for coffee and the crossword, and the grill is right there for the nights nobody wants to be indoors. Red Adirondack chairs line the rail facing the lawn and the treeline, and in fall the whole view turns the color the Berkshires are famous for. The setting is the quiet, pastoral end of the county, and it puts a remarkable amount within a short drive. The historic Upper Sheffield covered bridge is about five minutes east, and Sheffield’s Main Street — an antiquing stretch people plan whole afternoons around — is under ten. Hikers have it especially good: the Appalachian Trail crosses just north, Race Brook Falls is a ten-minute drive to a trailhead that climbs toward Mount Everett, and Bartholomew’s Cobble, with its easy loops above the Housatonic, is about twelve minutes south. Ski Butternut and Great Barrington’s restaurants, bookshops, and river walk are both roughly twelve to fifteen minutes north, with Catamount about twenty minutes west and Bash Bish Falls a scenic half-hour on. Push a little farther and Stockbridge opens up in about twenty minutes for the Norman Rockwell Museum and the Berkshire Botanical Garden, with Tanglewood around half an hour and Jacob’s Pillow closer to forty. Come for leaf season, ski season, a reunion, or a long summer week with nowhere to be. Bow & Beam handles all of it — and then hands you a deck chair and a view to finish the day on. Property Manager provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. Visiting the Berkshires is a must for anyone looking to pair a gorgeous natural landscape with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods here makes it easy to enjoy a wide range of outdoor activities, from rafting and fishing to ziplining and hiking. Stunning in any season, this region is famous for its food scene, which values local ingredients, and you’ll find many farm-to-table establishments in the southern areas. Explore classic New England architecture, a growing array of performing arts, and dozens of towns and trails. The Berkshires are waiting with variety and beauty you won’t find anywhere else. Local Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort Home Truths: - Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without Property Manager’s approval there is a fine of $500 per pet. - This home does not have central air conditioning. Cooling is provided by two mini-split units — one servicing the main floor and another in the primary bedroom — and ceiling fans in all bedrooms. Central heating is available for cooler seasons. - This home is not step-free. There are stairs at the entrance, and the living spaces and bedrooms are spread across three levels connected by interior stairs. One bedroom and a full bathroom are located on the main level. Please consider this when traveling with guests who have mobility needs. - The home is served by an on-site 500-gallon propane tank. - The living room wood stove is wood-burning. Firewood is not provided. - The home sits on 3.5 wooded acres in a quiet rural pocket of the Berkshires. Wildlife, insects, and dark, unlit surroundings after sunset are a normal part of the area. - There is a working cannabis and flower farm nearby. Depending on the season and wind direction, you may notice agricultural odors outdoors. Parking Details: - On-site parking is available for up to 6 vehicles. The driveway comfortably fits about 4 cars; the remaining spaces are tighter and may require some maneuvering, so plan on carpooling if your group is arriving in more than four vehicles. There is no garage access and no EV charger at this home. Street parking is not permitted. This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at Property Manager than the health, safety, and experience of our guests & staff. We’ve enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards. IDs will be requested for verification after booking. All bookings over 28 days require a security deposit. We report and prosecute all Credit Card Fraud. STR Permit: C0571542670 Licence number: C0571542670

Historic South Lee Apt 2 Mi to Main Street

Lee, MA, US
2 Bedrooms • 4 Guests

Nov 7 - 10
$516 night

Built in 1815 | Spacious &amp; Serene Back Gardens Immerse yourself in a piece of South Lee history with a stay at this charming vacation rental. The unit&#39;s neighborhood is on the National Register of Historic Places, boasting a storied past, including being the birthplace of a Supreme Court justice in 1822. When you aren&#39;t exploring local galleries or hiking forest trails, relish quiet evenings by the fire or drinks in the backyard. Get ready to start your own Berkshires story — it starts here! -- THE PROPERTY -- C0195461500 INDOOR LIVING - Dining table, electric fireplace - Washer &amp; dryer - Baseboard heating, window A/C unit OUTDOOR LIVING - Outdoor seating areas - Spacious lawn KITCHEN - Dishwasher, refrigerator, stove/oven, microwave - Drip coffee maker, Keurig, Italian press - Toaster, blender - Cooking basics, dishware &amp; flatware ACCESSIBILITY - Single-level apartment, 2 steps to enter PARKING - Driveway (2 vehicles) -- THE LOCATION -- - 7 miles to Tanglewood - 12 miles to Jacob&#39;s Pillow - 5 miles to Norman Rockwell Museum - 7 miles to October Mountain State Forest - 15 miles to Hancock Shaker Village -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $75 fee (+ fees &amp; taxes, 1 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in SECURITY CAMERA INFORMATION - 2 exterior devices - Location: front door, side of house - Coverage: driveway, side driveway, side entrance

6 Mi to Tanglewood! High-End Lee Apartment

Lee, MA, US
2 Bedrooms • 4 Guests

Dec 25 - 30
$638 night

High-Speed WiFi | Upgraded Kitchen | Private Forest-View Balcony | 2010 Addition to 1738 Property Kick off your next Berkshire getaway at this Lee vacation rental, where historic soul meets modern luxury! The 2-bed, 1-bath apartment serves as a launchpad for the arts and adventure — wake up to serene views before hiking the AT, fishing, or browsing the Norman Rockwell Museum. After an evening performance at Tanglewood, return home to recharge in style. Secure this New England sanctuary today! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed - Additional Sleeping: 1 portable crib APARTMENT FEATURES - Balcony - Smart TV, board games - Electric fireplace - 2010 addition to historic property built in 1738 KITCHEN - Refrigerator, stove/oven, dishwasher - Drip coffee pot, French press (starter coffee provided) - Toaster oven, microwave - Cooking basics, dishware &amp; flatware - Spices - 4-person dining table, counter seating, high chair GENERAL - Free WiFi (300 Mbps) - Central A/C &amp; heating, ceiling fan - Washer &amp; dryer, iron/board - Linens &amp; towels - Complimentary toiletries, hair dryer, hangers - Keyless entry FAQ - 1 exterior security camera (facing driveway) ACCESSIBILITY - Single-story apartment - 1 interior flight of stairs to access PARKING - Driveway (1 vehicle) -- THE LOCATION -- - 0.9 miles to downtown Lee - 2 miles to Lee Premium Outlets - 4 miles to Stockbridge, famous for Norman Rockwell&#39;s &#39;Street Scenes&#39; - 4 miles to Goose Pond Reservation &amp; October Mountain State Forest - 11 miles to Jacob&#39;s Pillow - 55 miles to Albany International Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story apartment requires 1 interior flight of stairs to access - Your safety matters. This property features 1 exterior security camera located outside the front door facing the driveway. It is outward facing and does not look into any interior spaces. The camera actively records audio and video Licence number: C0195461500;C0195461500;C0550811500;C0550811500;C0195461500;C0550811500;C0195461500

Vacation Rentals in Otis by Amenities & Features

Get to Know Otis

Otis, Massachusetts, nestled in the picturesque Berkshire Hills, is a serene and inviting destination for travelers seeking a blend of outdoor adventure and small-town charm. This quaint New England town is particularly enchanting for those looking to escape the hustle and bustle of city life and immerse themselves in nature. The town's proximity to the scenic Otis Reservoir and the Farmington River makes it a haven for water enthusiasts. Visitors can enjoy a variety of activities such as boating, fishing, and swimming during the warmer months. The reservoir, being the largest body of water for recreational use in Massachusetts, offers ample space for water sports and relaxation. For those who prefer land-based pursuits, Otis is surrounded by lush forests and rolling hills that are perfect for hiking, mountain biking, and wildlife watching. The nearby Otis Ridge, a family-friendly ski area, provides opportunities for skiing and snowboarding in the winter, making Otis a year-round destination for outdoor recreation. The town also boasts a rich cultural scene with the Otis Cultural Council promoting arts and culture within the community. Events such as concerts, art shows, and craft fairs are common, offering visitors a taste of local talent and creativity. Autumn in Otis is particularly magical, as the foliage transforms the landscape into a vibrant tapestry of reds, oranges, and yellows. Leaf peeping and fall festivals draw visitors from all over to experience the quintessential New England fall. For a more relaxed experience, the town's bed and breakfasts and country inns provide cozy accommodations that often reflect the historical charm of the area. Local dining options range from home-style cooking to gourmet cuisine, with many establishments using fresh, locally-sourced ingredients. In essence, Otis, Massachusetts, is a destination that offers a peaceful retreat into nature's beauty, complemented by a warm community spirit and a variety of activities to suit all ages and interests. Whether you're paddling on the tranquil waters of the reservoir, exploring the verdant trails, or simply enjoying the town's cultural offerings, Otis is a place where memories are made and the pace of life is just right.
Otis, Massachusetts, nestled in the picturesque Berkshire County, experiences a classic New England climate with four distinct seasons, each offering its own unique appeal to visitors. Winter, from December to February, is cold and snowy, with temperatures often ranging from the low 20s to mid-30s Fahrenheit. This season transforms the landscape into a winter wonderland, perfect for snowshoeing, skiing, and cozy evenings by the fire. The area receives a significant amount of snowfall, which is ideal for winter sports enthusiasts. Spring, from March to May, brings a gradual warming trend with temperatures typically ranging from the mid-30s to the high 60s. This season can be unpredictable, with late snowfalls or early heatwaves. The melting snow and spring rains contribute to the lush greenery that begins to emerge, making it a beautiful time for nature walks and witnessing the awakening of local flora. Summer, from June to August, is warm and the most popular time for visitors. Temperatures usually hover between the high 60s and low 80s, providing ideal conditions for outdoor activities such as hiking, boating on Otis Reservoir, and exploring the scenic countryside. Humidity can be moderate, but it's generally comfortable, especially in the evenings. Autumn, from September to November, is arguably the most picturesque season in Otis. The foliage turns vibrant shades of red, orange, and yellow, creating a breathtaking backdrop for drives, hikes, and photography. Temperatures range from the low 70s in early September to the mid-30s by late November. This season is also drier, with less precipitation than spring and summer, making it a favorite time for visitors seeking the quintessential New England fall experience. The climate is especially pleasant during the late spring and early fall when temperatures are moderate, and the natural beauty of the area is at its peak. These shoulder seasons offer a respite from the summer crowds and the winter chill, allowing for a more relaxed exploration of Otis and its surroundings. Whether you're looking to enjoy the snow-covered hills of winter, the blooming landscapes of spring, the sunny days of summer, or the fiery foliage of fall, Otis, Massachusetts, offers a classic New England climate that caters to a variety of outdoor pursuits and aesthetic pleasures throughout the year.
Otis, Massachusetts, nestled in the picturesque Berkshire Hills, offers a serene escape with a cultural twist that will delight travelers with a love for the arts, history, and local customs. While Otis is a small town, its proximity to the cultural hubs of the Berkshires makes it an excellent base for exploring the region's rich offerings. Begin your cultural journey at the Norman Rockwell Museum in nearby Stockbridge, which houses the world's largest collection of original Rockwell art. This museum celebrates the legacy of an American icon and provides insight into the artist's life and times. The museum's pastoral setting also reflects the natural beauty that has inspired artists throughout the region's history. For live music enthusiasts, Tanglewood in Lenox is a short drive away. This famed summer home of the Boston Symphony Orchestra hosts an array of classical, jazz, and popular music performances in an idyllic outdoor setting. The annual Tanglewood Music Festival is a highlight, drawing music lovers from around the world. Art galleries abound in the Berkshires, with a concentration in nearby Great Barrington and Lenox. These towns are home to a variety of galleries showcasing the work of local and regional artists, from contemporary pieces to traditional crafts. The Schantz Galleries in Stockbridge is renowned for its exceptional collection of contemporary glass art. History buffs will appreciate the area's rich heritage, exemplified by sites like The Mount, Edith Wharton's home in Lenox. This beautifully restored estate offers a glimpse into the life of one of America's greatest writers and reflects the Gilded Age's opulence. The Berkshire Scenic Railway Museum in Lenox also offers a nostalgic look at the region's railroading past. Local customs can be experienced at the many seasonal festivals and events that take place in the Berkshires. The fall foliage season is celebrated with harvest festivals and craft fairs, while the winter months bring opportunities for cozy cultural experiences, such as community theater productions and historical society events. For a taste of local cuisine, Otis and its surrounding towns offer charming eateries where you can savor New England classics and farm-to-table fare. The Berkshires are also known for their artisanal food producers, so be sure to sample locally made cheeses, preserves, and baked goods. In Otis and the surrounding Berkshire region, the blend of natural beauty and cultural richness creates a unique and inviting atmosphere for travelers seeking a tranquil yet culturally enriching getaway.
Otis, Massachusetts, nestled in the picturesque Berkshire Hills, is a delightful destination for families traveling with children. This small town offers a tranquil escape with a variety of outdoor activities that will keep the little ones engaged and entertained. During the warmer months, Otis Reservoir and Tolland State Forest provide the perfect backdrop for a family day out. Children can splash around in the lake, build sandcastles on the beach, or enjoy a picnic by the water. For the more adventurous families, kayaking and paddleboarding are popular activities on the reservoir, offering a fun way to explore the scenic surroundings. Hiking is another great way to immerse your family in nature. The trails in Otis are suitable for all ages, with paths that meander through lush forests and lead to stunning views. The Farmington River Trail, for example, is an easy hike that follows the river and is perfect for spotting local wildlife. In the winter, Otis Ridge Ski Area becomes a wonderland for families. This small, family-friendly ski resort is ideal for children learning to ski or snowboard, with gentle slopes and a ski school that offers lessons for beginners. The cozy atmosphere and manageable size of the ski area ensure that parents can relax while the kids enjoy the snow. For a unique experience, visit the Otis Poultry Farm, where children can see a working farm in action and learn about the animals. They might even have the chance to collect eggs or feed the chickens, providing a hands-on educational experience. When it's time to unwind, the Great Barrington Libraries often host family-friendly events, including story times and craft activities that are perfect for a quieter day. These community gatherings are a wonderful opportunity for children to interact with locals and make new friends. Dining in Otis is also a family affair, with several restaurants offering menus that cater to younger palates. Enjoy a hearty meal in a relaxed setting where everyone in the family can find something to their liking. Otis, Massachusetts, may be small, but its charm and array of activities make it a hidden gem for families seeking a peaceful retreat with plenty of opportunities for outdoor fun and learning. Whether you're paddling on the lake, hiking through the forest, or hitting the slopes, Otis is a destination that will create lasting memories for the whole family.
Otis, Massachusetts, nestled in the picturesque Berkshire Hills, is a sanctuary for outdoor enthusiasts and nature lovers. This quaint town offers a serene escape into the wilderness, with a variety of natural wonders and activities that cater to those seeking a connection with the great outdoors. The crown jewel of Otis is the Otis Reservoir, the largest body of water for recreational use in Massachusetts. Here, visitors can indulge in boating, fishing, and swimming during the warmer months. The reservoir's clear waters and scenic surroundings make it a perfect spot for kayaking and canoeing, offering a peaceful paddle experience. For hikers, Otis is a gateway to the Appalachian Trail, which provides some of the most stunning vistas in the region. The trail offers a range of hiking experiences, from leisurely walks to challenging climbs, and is a great way to immerse oneself in the diverse flora and fauna of the Berkshires. The nearby Beartown State Forest is another haven for nature lovers. With over 12,000 acres of forested land, it features miles of trails for hiking and mountain biking. In the winter, the forest becomes a wonderland for cross-country skiing and snowshoeing. The Benedict Pond within the forest is a tranquil spot for fishing and picnicking, surrounded by the lush greenery of the Berkshires. For those interested in a more leisurely outdoor activity, the Tolland State Forest offers a beautiful setting for picnicking and wildlife observation. The forest's location along the Farmington River also provides opportunities for a refreshing swim or a relaxing day of fishing. Otis also boasts a number of smaller trails and conservation lands, such as the Otis Ridge, which in the winter months transforms into a family-friendly ski area. The gentle slopes are ideal for beginners, while more experienced skiers can enjoy the challenging terrain. For a truly unique experience, visitors can explore the natural beauty of Otis by horseback. Local stables offer guided trail rides that meander through the countryside, offering a different perspective on the region's natural splendor. In Otis, the connection with nature is palpable. With its pristine lakes, lush forests, and rolling hills, this destination is a treasure trove of outdoor activities and natural wonders, providing a perfect backdrop for those looking to escape the hustle and bustle and reconnect with the earth's beauty.
Otis, Massachusetts, nestled in the picturesque Berkshire County, offers a serene escape into nature. While it may not have the extensive transportation networks of a major city, there are still several ways to reach and explore this charming New England town. Most travelers arrive in Otis by car, as it is conveniently located near major highways such as the Massachusetts Turnpike (I-90). Driving provides the flexibility to explore the scenic countryside at your own pace. For those flying in, the nearest major airport is Bradley International Airport in Windsor Locks, Connecticut, about an hour's drive away. Car rentals are available at the airport, and it is advisable to secure a vehicle for the duration of your stay in Otis. Public transportation options are limited in this rural area. However, during the peak tourist seasons, there may be local shuttle services connecting Otis to nearby attractions or towns. It's best to check with local tourism offices for the most current information on these services. Once in Otis, getting around is primarily done by car. The town itself is not known for being particularly walkable, as attractions and amenities are spread out. However, for outdoor enthusiasts, there are plenty of opportunities to walk, hike, or bike within the natural landscapes. The Farmington River and Otis Reservoir offer beautiful settings for outdoor activities, and the nearby Appalachian Trail provides excellent hiking opportunities. For those interested in exploring the broader Berkshires region, having a car is essential. The area is known for its cultural attractions, such as Tanglewood, the summer home of the Boston Symphony Orchestra, and the Norman Rockwell Museum, both of which are a short drive from Otis. In summary, while Otis may not have the public transportation infrastructure of a larger city, it is accessible by car and close to an international airport. The town's rural charm and natural beauty are best enjoyed with the freedom of a personal vehicle, allowing visitors to fully immerse themselves in the tranquil and picturesque surroundings of the Berkshires.

Otis FAQs

Otis is a charming town in the Berkshire region of Massachusetts, known for its scenic beauty and outdoor activities. Visitors can enjoy hiking and wildlife viewing at Otis State Forest, boating and fishing on Otis Reservoir, and skiing or snowboarding at Otis Ridge Ski Area during the winter months. The Farmington River also offers opportunities for kayaking and tubing. For a more relaxed experience, explore the local art galleries, antique shops, and enjoy the quaint New England atmosphere.
The best time to visit Otis depends on what you want to do. Summer is perfect for water activities and hiking, with warm temperatures and lush greenery. Fall is famous for its stunning foliage, making it a great time for scenic drives and outdoor exploration. Winter attracts those interested in snow sports like skiing and snowboarding. Spring can be lovely as the area blooms, but it's also mud season, so some outdoor activities may be limited.
Otis does host several local events and festivals throughout the year. The Otis Ridge Ski Area often has winter events, and the town celebrates various holidays with community gatherings. For specific annual events, it's best to check the town's event calendar or contact the local chamber of commerce as these can change from year to year.
Otis offers a variety of dining options ranging from casual eateries to fine dining. You can find American classics, pizzerias, cafes, and some international cuisine. For a local experience, try the Otis Poultry Farm for fresh baked goods and deli items, or visit one of the cozy taverns for a hearty meal.
In Otis, you'll find a range of accommodations to suit different preferences and budgets. Options include bed and breakfasts, inns, vacation rentals, and campgrounds. There are also several lodges and cabins, particularly around the Otis Reservoir, which offer a more rustic and scenic stay.
Yes, Otis is a family-friendly destination. With its outdoor activities, such as hiking, boating, and skiing, there's plenty for families to do together. The town also has parks and community events that are suitable for children. The relaxed pace of life and the safe, natural environment make it an ideal place for a family vacation.

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