Vacation rentals in Winsted, CT with free parking

Explore 18 vacation rentals, homes, and villas with free parking in Winsted, CT for your next getaway or business trip. With on-site parking included in your stay, enjoy the comfort and privacy of a home filled with premium amenities such as Air Condition Homes, Best Affordable Homes and Great for Groups. Throughout your stay, come and go with ease, knowing parking is always convenient and close at hand. With options starting as low as $94 per night and homes offering up to 6 bedrooms and 6 bathrooms, it's easy to book a personalized stay designed for your comfort. With 24/7 local support and high-speed Wi-Fi, you can also stay connected and protected throughout your trip. Plus, Marriott Bonvoy members earn points on every stay, making each trip more rewarding than the last. Book your next stay with ease and enjoy the convenience of free parking.

18 Homes with Free Parking in Winsted

Peaceful Goshen Cottage w/ Screened Porch & Views!

Goshen, CT, US
3 Bedrooms 6 Guests
Aug 31 - Sep 2
$287 night

Searching for the perfect spot to escape the worries of city life? Look no further than this peaceful 3-bedroom, 1.5-bathroom vacation rental property! Secluded on the countryside of the stunning Goshen, Connecticut area, this retreat is sure to be as relaxing as it is exciting. Spend leisurely afternoons on the screened-in porch all your own, or head over to the city for some local fun - whether browsing shops, dining at restaurants, or taking part in the Litchfield Jazz Festival! -- THE PROPERTY -- Bedroom 1: Full Bed | Bedroom 2: Full Bed, Full Murphy Bed | Bedroom 3: Twin Bed Full of natural light and cozy charm, this 3-bedroom getaway has all the comforts of home. The unique structure has interesting details such as stained-glass windows, a screened-in porch and a wood-burning fireplace. A full kitchen equipped with all appliances and dishware provides you the space to create delicious meals without leaving the house. Dine in the formal dining area, or take the meal al fresco to your spacious yard with outdoor dining furniture. Cozy up in front of a fire in the evenings or enjoy a movie. You’ll love the peace and quiet of this house, and the comfort that will have you feeling right at home. -- THE LOCATION -- Roughly an hour outside of Hartford, this Connecticut haven is the perfect destination for long weekends any time of year. On summer days, grill burgers out on the patio after a scenic bike ride or a hike. Several ski areas such as Mohawk Mountain and Woodbury are a short drive away and make for a perfect day trip. Explore the charming town of Goshen and sample the shops and dining. However you spend your time away, this darling Connecticut home will have you relaxing the moment you step inside! -- REST EASY WITH US -- Evolve 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. -- ADDITIONAL DETAILS -- Key Residence Features: - Amenities include a fully equipped kitchen, free WiFi, fireplace, stained-glass windows, Apple TV, parking for 3 in the driveway, screened-in porch, gas grill, and more! FAQ: 2 exterior security cameras (facing out), well water - Ideal Goshen location with close proximity to the Litchfield Jazz Festival! - Nearest Commercial Airport: Bradley International Airport (40.9 miles) -- POLICIES -- - No smoking - No pets allowed - Must be 25 years or older to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Your safety matters. This property features 2 exterior security cameras. Camera 1 is above the driveway and back door facing the driveway. Camera 2 is on the front porch facing the stairs. The cameras are facing outward. They do not look into interior spaces. The cameras record video and sound when activated by motion - NOTE: The well water is filtered but has iron. It is safe to drink

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

Cornwall, CT, US
2 Bedrooms 8 Guests
Aug 26 - 28
night

Get in touch with your inner outdoorsman at this vacation rental in West Cornwall, CT! Boasting 2 bedrooms, 2 bathrooms, and a spacious loft, this cozy cabin promises endless fun both indoors and out. Hit the slopes at Mohawk Mountain Ski Area on winter days, or trek Bloody Mountain via the Welles Preserve Trail — located directly behind the property — in the summer. Refuel after your adventures with dinner at RSVP before heading home to kick back with a movie on the screened-in porch. -- THE PROPERTY -- Wraparound Deck | Hiking Trail Access On-Site | Pet Friendly w/ No Additional Fee Bedroom 1: Full Bed | Bedroom 2: Queen Bed | Loft: Queen Bed, 2 Twin Beds | Additional Sleeping: Pack 'n Play w/ Sheets INDOOR LIVING: Smart TV, wood-burning fireplace, wet bar, reading nook, ceiling fans, laptop-friendly workspace in Bedroom 1, crib OUTDOOR LIVING: Screened-in porch w/ hammocks & outdoor theater (not available in winter), charcoal grill (charcoal not provided), outdoor dining area, open yard, garden KITCHEN: Stove/oven, microwave, refrigerator, coffee maker, toaster oven, cooking basics, dishware/flatware, dishwasher, trash bags/paper towels, toaster GENERAL: Free WiFi, electric heating, 3 window A/C units (bedrooms & loft), washer/dryer, linens/towels, complimentary toiletries, laundry detergent, landline phone, clip-on high chair, kids' toys ACCESSIBILITY: 2-story cabin, 11 external steps required for entry, bedroom & bathroom on 1st floor PARKING: Driveway (4 vehicles), 220-volt outlet for EV chargers available on-site (plug/adapter not provided) -- THE LOCATION -- THINGS TO DO: Mohawk Mountain Ski Area (2 miles), Cornwall Co-Op Farm Market (2 miles), The Original Cornwall Farm Market (3 miles), West Cornwall Covered Bridge (4 miles) HIKING TRAILS: Welles Preserve Trail - Bloody Mountain (0.8 miles), Mattatuck Trail at Flat Rocks Road (6 miles), Pine Knob Loop Trail (7 miles), Appalachian Trail (8 miles) OUTDOOR REC: Cream Hill Lake (2 miles), Covered Bridge Electric Bike (3 miles), canoe & rafting rentals via Clarke Outdoors (4 miles), Housatonic River (6 miles), Mohawk State Forest (6 miles) AIRPORT: Bradley International Airport (44 miles) -- REST EASY WITH US -- Evolve 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 no additional fee - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This 2-story cabin requires 11 external steps for entry via the front door. There is a bedroom and bathroom on the 1st floor - NOTE: There are window A/C units in the loft and bedrooms. The rest of the home does not have air conditioning but has ceiling fans

Cozy Litchfield House w/ Fenced-In Yard & Fire Pit

Litchfield, CT, US
3 Bedrooms 7 Guests
Oct 28 - 30
$273 night

Relish in the luxuries of this 3-bedroom, 2-bath Litchfield vacation rental! 'Stone-Peca' is the quintessential New England house, boasting modern amenities, a fully equipped kitchen, outdoor entertainment space, and a fenced-in yard where your furry friend will love to run around. This home provides the perfect blend of privacy and convenience, with easy access to quaint shops and top-notch restaurants. Don't forget to ski at Mohawk Mountain or hike at Burr Pond State Park while you're here! -- THE PROPERTY -- Dog Friendly w/ Fee | Walk to Town Center | Desk Workspace Bedroom 1: Queen Bed | Bedroom 2 (Pink Room): Queen Bed | Bedroom 3 (Brown Room): Queen Bed | All-Season Porch: Twin Futon OUTDOOR LIVING: 4-season sun porch, fenced-in backyard, deck, patio, outdoor dining area, umbrellas, gas grill, front porch, patio furniture, fire pit, 2 bicycles INDOOR LIVING: 2 Cable TVs, DVD player, books, 6-person dining table, ceiling fans KITCHEN: Fully equipped w/ stainless steel appliances, breakfast bar, drip coffee maker, KitchenAid mixer, tea kettle, toaster, food processor, Instant Pot, spices, dishware/flatware GENERAL: Free WiFi, washer & dryer FAQ: Ring doorbell security camera, dog fee (paid pre-trip), no A/C ACCESSIBILITY: 2 steps required to enter, multi-level home, sofa sleeper & full bathroom on 1st floor, 28 inches wide steep staircase to the 2nd floor PARKING: Driveway (4 vehicles) -- THE LOCATION -- VINEYARDS: Haight-Brown Vineyard (1.6 miles), Sunset Meadows Vineyards (3.9 miles), Miranda Vineyard (5.5 miles), Hawk Ridge Winery (8.6 miles), Connecticut Valley Winery (9.8 miles) SKI: Mohawk Mountain Ski Area (12.0 miles), Ski Sundown (20.7 miles), Mount Southington Ski Area (23.3 miles), Thunder Ridge Ski Area (34.0 miles), Catamount Mountain Resort (38.3 miles), Butternut Ski Area & Tubing Center (38.3 miles), Otis Ridge (38.4 miles) LOCAL DINING: Village Restaurant (0.4 miles), @ The Corner (0.5 miles), Bohemian Pizza and Tacos (1.2 miles), DaCapo of Litchfield (3.7 miles), Arethusa al Tavolo (3.7 miles), 5-Diamond Restaurant at Winvian Farm (4.1 miles), Venetian Restaurant (6.3 miles) ATTRACTIONS: Goshen Fairgrounds (6.2 miles), Goshen Historic District (6.3 miles), Action Wildlife (6.8 miles), Torrington Country Club (7.9 miles), Railroad Museum-New England (9.6 miles), New England Carousel Museum (17.0 miles), Farmington River Tubing (20.6 miles), Brookfield Craft Center (26.4 miles) GET OUTSIDE: Topsmead State Forest (2.9 miles), Mohawk State Forest (9.4 miles), Stillwater Pond State Park (9.8 miles), Burr Pond State Park (12.8 miles), State Park (14.1 miles), Lake Compounce (20.0 miles), Lime Rock Park (21.8 miles) AIRPORT: Bradley International Airport (38.3 miles) -- REST EASY WITH US -- Evolve 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 & taxes, 2 pets max, dogs only) - No events, parties, or large gatherings - Please observe quiet hours after 12:00 AM - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This multi-level home requires 2 steps to enter; there is a sleeper sofa and a full bathroom on the 1st floor - The property does not offer A/C - Your safety matters. There is a Ring doorbell security camera, located next to the front door facing out. It does not look into any interior spaces

Mohawk Mountain Retreat - 5 Mins to Skiing

Cornwall, CT, US
5 Bedrooms 9 Guests
Aug 31 - Sep 2
$543 night

Mohawk Mountain Retreat is a spacious 5 bed, 3.5 bath escape located just minutes from the hamlet of Cornwall, only 2.5 hrs from NYC & under 3 hrs from Boston. This elegantly-designed, spacious post & beam home features a striking red brick chimney & invites you to get cozy by one of its two brick fireplaces, relax under the charming gazebo, or unwind in the four-season sunroom. Nearby towns: Cornwall (5mins), Sharon (15mins), Falls Village (15mins), Kent (15mins), Litchfield (20mins) Mohawk Mountain Retreat is set amidst the picturesque New England tableaux of Litchfield County, Connecticut, and has the outdoor pursuits of the foothills of the Berkshire Mountains on its doorstep. Elegantly-designed and spacious, the home presents a classic pitched roof, dormer windows, exposed beams, and a striking red brick chimney. Enter through the front door into a cozy sitting room with a gas fireplace which leads into an open concept kitchen, dining and living area with a TV and wood burning fireplace. Head to the large sunroom (our favorite space in the house) or grab a book or a cup of coffee into the lounge and start your day appreciating the serene garden views. One guest bedroom is located on the main floor with a queen size bed looking out through the floor-to-ceiling bay windows with a view of the front garden. Another guest bedroom is located above the garage offering a king size bed and ensuite bathroom with a tub/shower combo. Upstairs, there are three bedrooms including the master bedroom which offers a king size bed, TV, ensuite bathroom with a walk-in shower and views out to the gazebo and pond. One guest bedroom has two twin beds that can be converted into a king while the other offers a double bed. A shared bathroom with a clawfoot tub & shower combo is conveniently located on the landing between the 1st and 2nd floors. The grounds feature delightful stone walls, perennial plantings, a children’s play area, a fire pit and include a sweeping bluestone patio with comfy seating, an umbrella for shade, grill and dining table making this the perfect place for al fresco meals or evening get togethers. Gather in the gazebo for some additional shade on a hot day, or take quiet time to sit by the ornamental pond. Mohawk Mountain Retreat is a dynamite year-round destination - an ideal spot for families or groups seeking a peaceful countryside escape with plenty of space to relax and entertain. Mohawk Mountain Retreat is just 2.5 hours from New York City & under 3 hours from Boston. A car is essential for getting there and exploring the area. The main access routes for NYC are the I-684 S, NY-22 S and I-87 S. The main access routes for Boston are the I-84 E, I-90 E and CT-4 E. We strongly recommend a 4x4 or a car with four-wheel drive, especially in winter, to handle snow and gravel roads.

Lakefront Granby Escape w/ Private Dock & Kayaks!

Granby, CT, US
2 Bedrooms 6 Guests
Aug 26 - 29
$276 night

Complete with 2 bedrooms, 1 bath, a brick fireplace, and pristine water views, this vacation rental will check off everything on your lake house wish list. Clear your mind with a relaxing paddle on the water and bring along your fishing gear for some morning casts. Come autumn, explore leaf-peeping trails and relish in the vibrant foliage. With ski mountains, breweries, apple orchards, and scenic hikes just minutes away, this lakefront retreat makes for the quintessential New England vacation. -- THE PROPERTY -- Deck w/ Lake Views | Free WiFi (High Speed) | Modern Amenities | On the Water Spend your next family getaway or writer’s retreat soaking in the picturesque New England countryside at this cozy lakefront cottage. Bedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds | Downstairs Den: Sleeper Sofa OUTDOOR LIVING: Private dock, deck w/ Adirondack chairs & gas grill, outdoor dining area, 4 single-seat hard-shell kayaks KITCHEN: Fully equipped, cooking basics, stainless steel appliances, toaster, drip coffee maker, Crock-Pot, blender, knife set, dishware/flatware INDOOR FEATURES: 2 Smart TVs w/ cable, brick fireplace, 6-person farmhouse dining table, wood beam ceilings, telescope, ceiling fans, separate living areas, wall-to-wall windows, open layout GENERAL: Washer/dryer, towels/linens, hair dryer, window A/C units, beach gear, games FAQ: Exterior security cameras (home entrances), lots of stairs required for access PARKING: Designated parking (2 vehicles, stairs required for access), driveway parking prohibited -- THE LOCATION -- MANITOOK LAKE (on-site): Swimming, fishing, kayaking OUTDOOR RECREATION: Granbrook Park (4.1 miles), Hatchett Hill Wilderness Area (5.8 miles), Enders State Forest (6.3 miles), Cowles Park (7.0 miles), Indian Council Caves (10.4 miles), Penwood State Park (12.5 miles), People’s State Forest (15.7 miles) ATTRACTIONS: Old Mill Pond Village (1.3 miles), Clark Farms Inc at Bushy Hill Orchard (2.9 miles), Maple View Farm (3.1 miles), Lost Acres Vineyard (4.2 miles), Six Flags New England (14.9 miles), Downtown Hartford (18.1 miles) GOLF: Copper Hill Golf Club (4.4 miles), Edgewood Golf Course (5.8 miles), The Ranch Golf Club (8.2 miles) SKIING: Ski Sundown (14.1 miles), Mount Lakeridge (23.9 miles), Otis Ridge (29.3 miles), Butternut Ski Area & Tubing Center (38.2 miles), Mohawk Mountain Ski Area (39.2 miles) AIRPORT: Bradley International Airport (10.2 miles) -- REST EASY WITH US -- Evolve 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 - No driveway access for this property - NOTE: This property requires stairs and may be difficult for guests with limited mobility - NOTE: Your safety matters. This property features exterior security cameras, located above the lower level side door and one facing the front entrance. They do not look into interior spaces - NOTE: Designated upper-level parking is available for 2 vehicles and requires a long staircase to reach the property - NOTE: The driveway is on the neighbor's private property and is not to be used. Vehicles may be towed at the guest's expense. Please use the designated parking

Steepletop - Nature Lovers Paradise with Rec Room

New Marlborough, MA, US
4 Bedrooms 8 Guests
Aug 26 - 28
$336 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

Meadow Top Cottage: Countryside Cottage on 72 Acres

New Marlborough, MA, US
3 Bedrooms 6 Guests
Aug 26 - 28
$316 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

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

Monterey, MA, US
3 Bedrooms 6 Guests
Aug 30 - Sep 2
$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 -- Evolve 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

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

Sheffield, MA, US
4 Bedrooms 14 Guests
Aug 26 - 28
$343 night

Welcome to Copper Kettle Farm by AvantStay, 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. AvantStay 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 AvantStay’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

Hike, Bike & Relax: Huckleberry Hill Home w/ Yard!

Avon, CT, US
5 Bedrooms 6 Guests
Sep 5 - 8
$273 night

2,016 Sq Ft | Fireside Unwinding | 10 Mi to Talcott Mtn State Park Your New England adventure begins at this classic Avon vacation rental! With a spacious interior and a dining room ideal for family gatherings, the home is thoughtfully designed for group comfort. Grab your hiking boots for a trip to Heublein Tower or enjoy a quiet afternoon in the yard. Nestled on Huckleberry Hill, just 6 miles from downtown shops, this gem is a standout choice for those seeking both peace and proximity. -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 full bed - Bedroom 3: 1 twin bed - Bedroom 4: 1 twin bed - Bedroom 5: 1 twin bed LIVING FEATURES - Flat-screen TV, fireplace - Formal dining room - Private yard - Shower/tub combo, walk-in shower KITCHEN - All major appliances, including dishwasher - Keurig coffee maker (starter coffee provided), toaster - Cooking basics, trash bags/paper towels, dishware &amp; flatware GENERAL - Window A/C unit, gas radiator heating - Washer/dryer, iron/board - Linens/towels, complimentary toiletries, hair dryer - Free WiFi FAQ - Barn not for guest use - 1 exterior security camera (facing out) ACCESSIBILITY - 2-story home - 1 step to enter - 1 bedroom on 1st floor PARKING - Driveway (3 vehicles) -- THE LOCATION -- - 1 mile to Farmington River &amp; Historic Farmington River Iron Bridge - 1 mile to Sweetheart Mountain Trailhead - 5 miles to Pine Grove School House - 6 miles to Farmington Valley Greenway - 6 miles to Farmington Canal Heritage Trail - 6 miles to Avon Old Farms School - 8 miles to Miss Porter’s School - 10 miles to Talcott Mountain State Park - 23 miles to Bradley International Airport -- REST EASY WITH US -- Evolve 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 2-story home requires 1 step to enter and features 1 bedroom on the 1st floor - The barn is not for guest use - Your safety matters. This property features 1 exterior security camera located on the back exterior, facing outward toward the backyard. It does not look into any interior spaces. The camera records video and sound when activated by motion

Unique Geodesic Dome Escape in Nature!

Warren, CT, US
3 Bedrooms 6 Guests
Aug 26 - 28
$303 night

Dog Friendly w/ Fee | Dedicated Workspace | Near Lakes, Trails &amp; Wineries Escape to Connecticut’s scenic Litchfield Hills at this unique 3-bed, 2-bath dome house in Warren. Set on 2.5 private acres, this summer retreat is close to hiking trails, lakes, wineries, and charming New England towns. Spend your days kayaking, exploring Kent Falls, enjoying local vineyards, or relaxing outdoors beneath the trees. Perfect for families, couples, or friends seeking a peaceful getaway. -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 full bed - Living Room: 1 queen sleeper sofa - Den: 1 queen sleeper sofa INDOOR LIVING - Smart TVs, wood-burning stove - Board games, books - Home office, dining table - En-suite bathroom OUTDOOR LIVING - Furnished deck, outdoor dining set - Gas fire pit, electric BBQ grill - Organic vegetable garden (available for guests use) KITCHEN - Refrigerator, stove/oven, microwave, dishwasher - Keurig &amp; drip coffee makers (coffee provided), toaster, blender - Dishware &amp; flatware, cooking basics GENERAL - Keyless entry, self check-in, free WiFi - Washer &amp; dryer, laundry detergent, trash bags/paper towels - Towels/linens, complimentary toiletries, hair dryer - Built-in AC &amp; heat pump units (main living areas) - Portable A/C units &amp; baseboard heating (bedrooms) FAQ - Pet fee (paid pre-trip) - 2 exterior security cameras (deactivated, facing out) ACCESSIBILITY - 2-story cabin, 1 step required to enter - 2 bedrooms &amp; 1 bathroom on main floor PARKING - Driveway (4 vehicles) -- THE LOCATION -- - Near hiking trails &amp; nature preserves, farmers markets &amp; wineries - 3 miles to Kent Falls State Park - 4 miles to Lake Waramaug State Park, 6 miles to Warren Town Beach - 7 miles to the town of Kent - 11 miles to the town of Litchfield - 11 miles to Mohawk Mountain Ski Area - 11 miles to Clarke Outdoors: whitewater rafting - 56 miles to Bradley Int’l Airport -- REST EASY WITH US -- Evolve 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 indoors (outdoors permitted) - Pet friendly w/ $75 fee (+ fees &amp; taxes, dogs only, 1 max) - 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 cabin requires using 1 step to enter; there are 2 bedrooms and 1 bathroom on the 1st floor - Your safety matters. This property features 2 exterior security cameras. Camera 1 is by the front door, facing outward. Camera 2 is on the back of the home, facing the deck and backyard. These cameras do not look into any interior spaces. The cameras will be deactivated and won&#39;t record video or sound while guests are present

Modern Terryville Cottage w/ Deck & Lake View!

Bristol, CT, US
2 Bedrooms 4 Guests
Aug 26 - 28
$242 night

Experience a peaceful retreat by the lake at this modern Terryville vacation rental! Complete with 2 bedrooms, a luxury bathroom, and an inviting living room with an electric fireplace, this cottage offers relaxation and comfort in every corner. Dive into a summer of lake adventures and, traditionally on the 4th of July, enjoy a prime view of the fireworks display from the deck. After a day of outdoor activities, return home for a movie night on the 4K Smart TV! -- THE PROPERTY -- Recently Renovated | Central Location | Modern Marble Bathroom | Walk to Fall Mountain Lake Bedroom 1: Full Bed | Bedroom 2: Queen Bed COTTAGE HIGHLIGHTS: 4K Smart TV w/ surround sound, electric fireplace, laptop-friendly workspace, 4-person dining table, adjustable bed base w/ massage feature KITCHEN: Fridge, stove, dishwasher, Keurig coffee maker, microwave, cooking basics, toaster, dishware/flatware, trash bags/paper towels GENERAL: Free WiFi, keyless entry, central heating &amp; A/C, complimentary toiletries, linens/towels, ceiling fans, hair dryer ACCESSIBILITY: Single-story cottage, 2 steps to enter PARKING: Driveway (4 vehicles) -- THE LOCATION -- FALL MOUNTAIN LAKE (walking distance): Boating, swimming fishing, 4th of July firework show THINGS TO DO: Lake Compounce (6 miles), Mattatuck State Forest (9 miles), Mattatuck Museum (10 miles), Mount Southington Ski Area (10 miles), Hubbard Park (15 miles), Quassy Amusement &amp; Waterpark (17 miles), White Memorial Conservation Center (18 miles), Connecticut State Capitol (21 miles) CONNECTICUT HOT SPOTS (~38 miles): Yale University, Mystic Aquarium &amp; Seaport, Mohegan Sun &amp; Foxwood casinos, Visitor Center, Beinecke Rare Book and Manuscript Library, museums, theater, live music, wine trails, parks, pizza trails, boat tours AIRPORT: Bradley International Airport (36 miles) -- REST EASY WITH US -- Evolve 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 single-story property requires 2 steps to enter

Water-View Home in the Berkshires

Sheffield, MA, US
3 Bedrooms 6 Guests
Aug 30 - Sep 2
$328 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 -- Evolve 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

Bristol Condo Near ESPN HQ & Lake Compounce!

Bristol, CT, US
1 Bedrooms 4 Guests
Aug 26 - 28
$187 night

Furnished Balcony | Reserved Parking | &lt; 2 Mi to ESPN HQ This Sandpiper Woods vacation rental puts Bristol&#39;s best — ESPN HQ, Lake Compounce, and Muzzy Field — within easy reach. The cozy 2-story condo features a spacious interior with vaulted ceilings and a lofted TV room, plus an inviting furnished balcony off the bedroom. Summer brings Little League at the Eastern Region Complex, and fall means Rogers Orchards and the Apple Harvest Festival. Year-round Bristol awaits — book your stay now! -- THE PROPERTY -- CONDO FEATURES - Open interior w/ vaulted ceilings - Upstairs living room w/ Smart TV &amp; sleeper sofa - Wall unit A/C &amp; electric heat - Washer &amp; dryer - Furnished balcony off bedroom - 2 flat screen TVs - Furnished deck KITCHEN - Refrigerator, stove/oven, microwave - Cooking basics, dishware &amp; flatware, dishwasher - Keurig coffee maker, starter coffee included ACCESSIBILITY - 2-story condo, 1 step to enter - 12 steps to access main level PARKING - Community lot (1 reserved space #58) - Guest parking spaces available -- THE LOCATION -- - Single-story condo in the quiet Sandpiper Woods community less than 2 miles to ESPN HQ - 1-3 miles to Pine Lake Adventure Park &amp; Lake Compounce Amusement &amp; Water Park - 2-3 miles to The Carousel Museum &amp; American Clock &amp; Watch Museum &amp; Imagine Nation Children&#39;s Museum - 3-4 miles to Muzzy Field &amp; Little League Eastern Region Complex - 6 miles to Rogers Orchards - 6 miles to Mount Southington Ski Area - 3-7 miles to Farmington Canal Heritage Trail, Harry C. Barnes Memorial Nature Center &amp; Sessions Woods Wildlife Management Area - 11 miles to Hill-Stead Museum - 13 miles to Farmington River Trail - 18 miles to The Brownstone restaurant district - 21 miles to Talcott Mountain State Park - 32 miles to Mohawk Mountain Ski Area - 34 miles to Dover Beach - 40-42 miles to West Haven Apple Festival &amp; Maltby Lakes -- REST EASY WITH US -- Evolve 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

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

Monterey, MA, US
6 Bedrooms 16 Guests
Oct 5 - 7
$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 &amp; flatware, Keurig K-Duo, percolator, coffee provided, toaster oven, beverage fridge, trash bags &amp; paper towels GENERAL: Free WiFi, central A/C &amp; heating, complimentary toiletries, linens &amp; 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 &amp; 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&#39;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 -- Evolve 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 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

Lakeville Lodge - Family Friendly Home with Pool & Hot Tub

Salisbury, CT, US
3 Bedrooms 6 Guests
Sep 14 - 16
$843 night

Lakeville Lodge is a 3 bed, 2.5 bath retreat just 2.5 hrs from NYC and 3 hours from Boston, located in a quiet neighborhood just a short drive to Lake Wononscopomuc. This light filled, luxurious post and beam barn style home features a pool and hot tub for year round relaxation, an indoor basketball net, and a lovely outdoor living area. Nearby towns: Lakeville (5mins), Sharon (15mins), Canaan (15mins), Kent (30mins), Litchfield (35mins) Experience rustic craftsmanship at Lakeville Lodge, a secluded retreat with pool and hot tub set on generous acreage offering true peace and privacy. The post and beam barn style home features warm wood flooring, layered brick-and-timber textures, and expansive windows that allow natural light to flood the living spaces. The open concept living room welcomes you with cathedral ceilings, an impressive floor-to-ceiling brick chimney and a classic wood-burning stove that sits ready for cozy evenings. The seating area features plush, contemporary sofas and soft accent chairs arranged around a stylish round wooden coffee table with oversized windows that wrap the room in natural light and provide serene views of lush trees and open sky. Toss a few baskets on the unique soft play basketball hoop that takes advantage of the double height ceilings. The living area flows into a beautifully appointed dining and kitchen space featuring a long solid-wood dining table ideal for group meals or game nights, with a sliding door leading to the outdoor living room just beyond. The kitchen is crafted with natural wood cabinetry offering ample counter space for cooking and entertaining and a wall of windows with gorgeous views while you cook or socialize. A laundry room is available for guest use just off the kitchen. The primary bedroom, located on the main floor, offers a king size bed, laptop friendly workspace and an en-suite bathroom with a walk-in shower. Upstairs, the light-filled loft hosts a TV lounge with a comfortable sectional couch. and a wide selection of games for your group to enjoy. There are two additional guest rooms on this floor each with king size beds. These guest rooms share a bathroom with a shower/tub combo. The outdoor spaces of this home are top tier, with a spacious dining and lounging patio area with a grill and seating areas for meals or relaxation, and a charming fire pit lounge area complete with Adirondack-style chairs arranged on a stone patio. The pool with stone surround and hot tub offer relaxing retreats no matter the season, surrounded by lush lawn. The surrounding woodlands enhance the sense of seclusion, and the quiet neighborhood location is conveniently just outside of the charming town of Lakeville, known for Lake Wononscopomuc, Connecticut’s deepest lake. Lakeville Lodge is a year round retreat and a base for exploration of the beautiful surrounding Litchfield County towns, or a place to unplug and stay put. With ample room for your group, pool, hot tub and outdoor lounging, this is a fantastic location to book your next getaway. Lakeville Lodge is just 2.5 hours from New York City. The main access routes are the NY-22 S, I-684 S, Taconic State Pkwy and I-87 S. We strongly recommend a 4x4 or a car with four-wheel drive, especially in winter, to handle snow and gravel roads. Guests are not permitted to park in the garage. A/C: There are two split units: one in the living room and one in the primary bedroom.

Lakefront Otis Home w/ Stunning Views & Boats!

Otis, MA, US
2 Bedrooms 6 Guests
Sep 2 - 5
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 &amp; 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 -- Evolve 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: 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

Berkshires Cabin 2 Mi to Appalachian Trail!

Otis, MA, US
3 Bedrooms 7 Guests
Sep 1 - 4
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 trailing waterfalls of the Otis State Forest, as well as the slopes of Butternut Ski Area, 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 some 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 &amp; flatware, trash bags &amp; paper towels GENERAL: Free WiFi, central heating, complimentary toiletries, hair dryer, towels &amp; linens, washer &amp; dryer, iron/board FAQ: Stairs required to access, A/C: Not available, 1 Ring camera (facing driveway) PARKING: Driveway (4 vehicles) -- THE LOCATION -- HIKE &amp; 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 -- Evolve 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 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

Vacation Rentals in Winsted by Amenities & Features

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Vacation Rentals Near Winsted

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