Large group vacation rentals in Cavendish, VT

Explore 354 large group vacation rentals, homes, and villas in Cavendish, VT for your next getaway or business trip. With space for everyone, enjoy the comfort and privacy of a home designed for gathering, alongside premium amenities such as Best Affordable Homes. Throughout your stay, spend time together, share meals, and relax in spacious living areas that make group travel feel cohesive. With options starting as low as $65 per night and homes offering up to 8 bedrooms and 6 bathrooms, it's easy to book a stay that fits your group. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next group getaway with Homes & Villas by Marriott.

354 Great for Groups in Cavendish

17-Acre Vermont Escape w/ Panoramic Mountain Views

Cavendish, VT, US
6 Bedrooms 14 Guests
Sep 1 - 3
$578 night

Built in 1892, this classic yet modern Cavendish vacation rental exudes old-world charm and elegance! Every window in this 6-bedroom, 2-bathroom home offers a picturesque view, making you feel like you're living in a postcard. Kids and pets are welcome at this spacious home, so you can enjoy this getaway with all your loved ones. Whether you hit the slopes at Okemo Mountain, take a dip at Buttermilk Falls, or simply relax around the fire, you’ll be sure to make memories that last a lifetime. -- THE PROPERTY -- MRT-11153470-001 | 2,400 Sq Ft | Historic Home | Furnished Porch & Balcony | Pet Friendly w/ Fee Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Bedroom 5: Queen Bed | Bedroom 6: 2 Twin Bunk Beds w/ Twin Trundles | Additional Sleeping: Pack ‘n Play OUTDOOR LIVING: Fire pit, gas grill, panoramic mountain views, 17-acre property, hiking trail access nearby INDOOR LIVING: Smart TV w/ cable/satellite, books, board games, wood-burning stove KITCHEN: Stainless steel appliances (stove, double oven, fridge, microwave, dishwasher), teapot, blender, drip & Keurig coffee makers, cooking basics, Crockpot, dishware & flatware, spices, toaster GENERAL: Keyless entry, complimentary toiletries, central heating, free WiFi, trash bags & paper towels, linens & towels, washer/dryer SUITABILITY: 1 half step to enter, bedroom & bathroom on main floor, 2-story home FAQ: Pet fee (paid pre-trip), exterior Ring doorbell camera (facing front entry), no A/C ACCESSIBILITY: PARKING: Driveway (6 vehicles), 4WD recommended in spring -- THE LOCATION -- SKI RESORTS: Jackson Gore Base (10 miles), Okemo Mountain Resort (12 miles), Magic Mountain Ski Area (25 miles), Killington Resort (30 miles), Pico Mountain Ski Resort (32 miles) THE GREAT OUTDOORS: Weathersfield Trail (8 miles), Buttermilk Falls (11 miles), Healdville Trail (13 miles), Okemo State Forest (14 miles), Mount Ascutney State Park (15 miles) AREA ATTRACTIONS: Snow Country Snow Mobile (5 miles), Fox Love Golf Club (9 miles), Okemo’s Adventure Zone (10 miles), Wellwood Orchards (12 miles), Crown Point Country Club (13 miles), Calvin Coolidge Historic Site (19 miles) NEARBY CITIES: Ludlow (8 miles), Springfield (14 miles), Claremont (17 miles) AIRPORT: Rutland Southern Vermont Regional Airport (26 miles), Albany International Airport (97 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 w/ $50 fee (+ taxes & fees) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires 1 half step to access via the back door. Although there is a bedroom and bathroom on the 1st floor, additional interior stairs are required to access all other bedrooms - NOTE: The property is located on a long unpaved road, so four-wheel drive or all-wheel drive is recommended and may be necessary in the springtime to access the property - NOTE: The property does not have air conditioning - NOTE: Your safety matters. This property features a Ring Doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed

Convenient village condo w/ mountain views, close to Okemo, partial a/c, w/d

Proctorsville, VT, US
3 Bedrooms 8 Guests
Sep 21 - 23
$235 night

Nestled in the heart of the charming village of Proctorsville, this multi-level North Country Condo offers a cozy retreat for your Vermont getaway. With three bedrooms, two baths, and mountain and valley views, this third-floor condo is the perfect home base for exploring the Okemo Valley. The train bridge over the Black River is directly visible outside the kitchen windows. Enjoy modern amenities such as a washer/dryer, partial AC, and WiFi, ensuring a comfortable stay for you and your guests. Note: The wood-burning fireplace is not for guest use. The jets in the bathtub are not for guest use. Step outside your door to discover a variety of local eateries and a brewery just a stone’s throw away. During the summer months, immerse yourself in the vibrant community atmosphere with live music performances on the village green. Whether you’re a winter sports enthusiast or an outdoor adventurer, this condo is ideally located near Okemo Mountain for skiing, VAST snowmobile trails, scenic hiking routes, and the serene lakes region, all just a short drive away. For golf enthusiasts, the Fox Run Golf Club is close by, as well as picturesque hiking trails in the Proctor-Piper State Forest. Indulge in delicious meals at Murdock’s restaurant, sample craft brews at Outer Limits brewery, and explore the bustling village of Ludlow, all within easy reach of your accommodation. Relax in the comfortable living room, unwind in the cozy bedrooms, and take in the beautiful mountain views from the condo. Whether you’re seeking outdoor adventures or simply looking to unwind in a peaceful setting, this North Country Condo in Proctorsville, VT, offers the perfect blend of convenience and comfort for your vacation. Book your stay today and experience the best of Vermont’s natural beauty and local charm. Vermont Meals and Room Tax Number: MRT-11472019

Two-story townhome with forest/mountain view, gas fireplace, pool, gym & saunas

Proctorsville, VT, US
3 Bedrooms 10 Guests
Aug 25 - 27
$133 night

Enjoy easy access to Ludlow, Okemo Mountain Resort, and the best of Southern Vermont at this three-bedroom townhouse in Cavendish, the perfect home base for outdoor adventures year round. This two-story townhome sits among the treetops three miles east of Ludlow, with grounds that include a community pool, a fitness center, and saunas to relax you after a day on the slopes. Okemo Mountain Resort - a hub of skiing, snowboarding, tubing, hiking, and golf - is less than five miles west as well. The setting is serene and scenic, best taken in from the private balcony overlooking the woods. It’s a wonderful spot to sit with your breakfast, a cup of coffee, or a crossword puzzle in the afternoon. On winter days, come home to relax beneath two-story ceilings in the living room, where you can light the gas fireplace and stream a movie on TV as the snow piles up outside. There’s a well-equipped kitchen with stainless steel appliances for preparing hearty meals, a dining room table for family dinners and board games, and two more dens where you can escape with a movie - one downstairs and one in the upstairs landing. Of the three bedrooms (each with an attached bathroom), two are on the main floor and one is upstairs. RESORT AMENITIES -Swimming pool -Fitness center -Saunas THINGS TO KNOW Extra resort charge of $45 per person per day on Friday & Saturday and $25 per person per day Sunday - Thursday, or $250 for a 10-day punch card (1 punch per person per day). Spa services depend on the services selected. Prices are subject to change; it is best for guests to inquire directly at Castle Hill for pricing and access information. Amenities include a full service spa, heated outdoor pool (open during winter), hot tub, and fitness center. *Check with Castle Hill for availability, as these may not be available due to local restrictions. Resort amenities are available for a separate fee issued directly through the resort. Vermont Meals and Room Tax Number: MRT-11472019

Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!

Cavendish, VT, US
3 Bedrooms 8 Guests
Aug 25 - 28
$456 night

Discover the serenity of Cavendish and make lasting memories at this 3-bedroom, 2.5-bath vacation rental. Nestled in the heart of nature, this charming home offers everything needed for a relaxing getaway. Enjoy coffee on the deck while taking in the peaceful surroundings, gather around the fireplace on cooler nights, or cook up a delicious meal on the grill. With Okemo Mountain, Buttermilk Falls, and snowmobile trails nearby, adventure awaits at every turn when staying at this idyllic retreat! -- THE PROPERTY -- Meals & Rooms Tax License No. MRT-11153470-001 | Pet Friendly w/ Fee | 2,240 Sq Ft | 8-Person Hot Tub | 1 Mi to Snowmobile Trails Bedroom 1: King Bed | Bedroom 2: King Bed, Full Bed | Bedroom 3: King Bed, Queen Bed OUTDOOR LIVING: Furnished deck, gas grill, fire pit, private wooded property INDOOR LIVING: Smart TVs, wood-burning fireplace, dining table, open floor plan, board games KITCHEN: Fridge, stove, dishwasher, drip coffee maker, microwave, cooking basics, toaster, dishware/flatware, trash bags/paper towels, espresso machine GENERAL: Free WiFi, central A/C, complimentary toiletries, linens/towels, washer/dryer, ceiling fans, hair dryer, iron/board FAQ: 4WD required, no A/C, pet fee (paid pre-trip), external security camera (facing out) ACCESSIBILITY: Multi-level home, stairs required to enter, bedroom & bathroom on 1st floor PARKING: Driveway (4 vehicles) -- THE LOCATION -- ON THE MOUNTAIN: Okemo Mountain Resort (7 miles), Killington Resort (18 miles), Bromley Mountain Ski Resort (29 miles), Stratton Mountain Resort (34 miles) THE GREAT OUTDOORS: Ludlow Lakes Region (7 miles), Buttermilk Falls (10 miles), Okemo Mountain Forest (13 miles), Coolidge State Forest (13 miles), Mt. Ascutney State Park (20 miles), Moody Trails (25 miles) YEAR-ROUND FUN: Fox Run Golf Club (9 miles), American Precision Museum (21 miles), Cornish-Windsor Covered Bridge (21 miles), The Fort at No. 4 (23 miles) AIRPORT: Albany International Airport (96 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 w/ $60 fee (+ taxes & fees) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This multi-level home requires exterior stairs to enter, and interior stairs are required to access the 2nd-floor bedrooms - NOTE: Your safety matters. This property features an external security camera located on the front of the home 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 - NOTE: The property does not have air conditioning - NOTE: All-wheel or four-wheel drive is required to access the property due to the steep hill and unpaved road

Delightful house w/ hot tub, wrap-around deck, ping-pong-pool table, fireplaces

Ludlow, VT, US
4 Bedrooms 8 Guests
Aug 25 - 27
$186 night

Escape to this charming dog friendly house nestled in the serene woods of Ludlow, VT, just minutes away from the thrilling slopes of Okemo Mountain. This cozy 4-bedroom, 3-bathroom retreat is perfect for families and friends looking to unwind and enjoy the beauty of nature. With a wrap-around deck and a hot tub, you can soak in the tranquility while surrounded by lush greenery. (Note: upper wrap around deck unavailable until November 2025.) Inside, the home boasts a warm and inviting atmosphere, featuring two gas fireplaces to keep you cozy during chilly evenings. The spacious living area is ideal for entertaining, complete with a convertible ping-pong or pool table for endless fun. The fully equipped kitchen, with modern appliances including a fridge, stove, and dishwasher, makes meal preparation a breeze. With ample sleeping arrangements, including a king bed, queen bed, and double bed, everyone will find their perfect spot to rest after a day of adventure. Enjoy the convenience of a washer/dryer and partial AC for added comfort. Spend the day at nearby Fox Run Golf Club or get pampered at Castle Hill Resort and Spa. Whether you’re hitting the slopes, exploring nearby hiking trails, or simply relaxing in the hot tub, this Ludlow getaway offers the perfect blend of comfort and excitement. Book your stay today and create unforgettable memories in this woodland paradise!

Countryside, lakefront cabin with kayaks, balcony, & fast WiFi

Ludlow, VT, US
3 Bedrooms 8 Guests
Aug 30 - Sep 1
$143 night

Escape to the beautiful countryside of Vermont with this quiet, lakefront retreat. Camp Plymouth State Park, Fox Run Golf Club, Okemo Mountain Sky Resort, and Coolidge State Forest are all within a 10-mile radius, just ready for exploration! This home is set right next to the lake, offering amazing, picturesque views. Take the kayaks or canoe provided to find your zen on the calm, clear lake. Upon entry, you’ll be met with an open, light-filled interior thanks to the many viewing windows that look out into the trees. Relax and make yourself at home by resting on the plush furniture, streaming your favorite movies on the large TV, or curling up in the living room with a great book. Prepare grand meals in the full kitchen, equipped with stainless steel appliances and a formal dining table with 180-degree views. The open floor plan keeps the conversation flowing no matter where you are. Enjoy your meals outside by cooking on the gas grill and using the deck’s dining table. If you need to stay connected, a dedicated workspace with a desk and chair is available for remote work. Comfortable beds in spacious rooms ensure that everyone will receive a restful night’s sleep from the day’s adventures. Gather around the firepit to roast marshmallows or tell stories until the stars come out to dot the sky, making memories that’ll last a lifetime. Things to Know Check-in time: 4:00 PM Check-out time: 10:00 AM All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM No smoking is permitted anywhere on the premises. To use streaming services, guests must log in with their own credentials.

Lakefront home with amazing views, fireplace, firepit, & gas grill

Ludlow, VT, US
4 Bedrooms 8 Guests
Aug 27 - 29
$169 night

With lake access, amazing views, and an array of amenities, this Lake Rescue getaway is your perfect home away from home. The large, open kitchen, well-equipped with stainless steel appliances, provides ample meal prep space for the chef for your group. You can all gather around the home’s large dining table and enjoy home-cooked meals. After stepping into this spacious home, you’ll be greeted with an open, light-filled interior. Curl up next to the wood-burning fireplace or enjoy a movie night on the plush furniture. Outside, you can swim, or just kick back and look out over Lake Rescue. Explore Lake Rescue with one of the three kayaks available. There is even an outdoor firepit where you can stay warm as the stars come out overhead.Nearby Lake Rescue is perfect for swimming, kayaking, and fishing. Fantastic for the avid skier and snowboarder, Okemo Mountain Resort is just five miles south. And for hiking and beautiful scenery, Camp Plymouth State Park is also just a short drive away, so don’t forget your cameras! Things to Know Check-in time: 4:00 PM. Check-out time: 10:00 AM. All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM. No smoking is permitted anywhere on the premises. Please note that the dock, kayaks, porch furniture, and canoe are amenities that are only available in the summer.

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Ludlow, VT, US
4 Bedrooms 10 Guests
Aug 26 - 28
$618 night

Boasting the best modern cabin vibes both inside and out, this stylish retreat is more than ready to assist in making mountain memories to last a lifetime! Sitting right on the bank of Lake Rescue, there will be no delay in summer fun with a private dock, kayaks, paddleboards, and more to really soak up the lakeside lifestyle. Come winter, the skiers of the group will absolutely fall in love with this location as well, as Okemo Mountain Resort is just four miles south offering a wide array of ski runs for all experience levels and Killington is 17 miles north. Downtown Ludlow is also near the mountain where you can stock up on groceries, grab a bite to eat from a local restaurant, or pop into shops to snag a souvenir. Though the exterior will charm even the most design-oriented of guests, step inside and you will immediately be greeted by the rustic exposed ceilings, homey hardwood floors, and mountain decor that will allow everyone to feel welcome and relaxed in no time. Not to mention, the well-equipped, full kitchen complete with a gas range, beautiful white countertops, and all of the appliances needed to whip up tasty meals will be the perfect touch to make this an ideal home away from home. After a full day of skiing in winter or kayaking in summer, everyone will love gathering for a movie night in the living room or stepping out to the back deck to watch the sunset with a favorite cocktail in hand. With four bedrooms and two baths, this place is well-suited for two couples or a large family. Please note the top bunks and pull out beds are intended to comfortably accommodate children. The home also has a dedicated office and a desk set up in each bedroom, making it ideal for remote learning or work. Please note: the waterfront dock features approximately 60 steep steps to access which may be strenuous for some guests. Things to Know Check-in time: 4:00 PM Check-out time: 10:00 AM All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM No smoking is permitted anywhere on the premises. Kayaks and paddleboards are provided seasonally.

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!

Ludlow, VT, US
3 Bedrooms 8 Guests
Aug 25 - 27
$303 night

The quintessential Vermont mountain home, this 3-bedroom, 2-bath vacation rental hosts an in-the-country feel just moments from Okemo Mountain Resort. When the leaves turn, explore an abundance of local parks and trails, and, when flakes fall, shred the slopes with ease. Activities aside, you'll adore the stylish furnishings, modern amenities, and convenient walkability to Ludlow Village. Note to self: accommodates couples, families, and furry friends alike! -- THE PROPERTY -- Meals & Rooms Tax License No. MRT-11153470-001 | Pet Friendly (w/ Fee) | Okemo Mountain Views Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed, Twin Bunk Bed HOME FEATURES: 2 Smart TVs, farmhouse dining table, mudroom w/ ski storage, board games, ceiling fans, cozy & modern decor OUTDOOR SPACES: Front & back decks, private yard COUNTRY KITCHEN: Cooking basics, stainless steel appliances, breakfast bar w/ seating, spices, dishware & flatware, toaster, coffee bar w/ Keurig coffee maker & electric kettle (coffee & tea provided) GENERAL: Free WiFi, washer/dryer, towels/linens, hair dryer, iron/board, central heating, seasonal window A/C units, complimentary toiletries, shampoo, conditioner, body wash ACCESSIBILITY: 2-story home, 3 steps to enter, 2nd-floor bedrooms FAQ: Pet fee (paid pre-trip) PARKING: Driveway (3 vehicles), street parking (first-come, first-served) -- THE LOCATION -- LUDLOW VILLAGE (0.9 miles): Shops, restaurants, ski rentals, parks, local museum SKIING + BOARDING: Okemo Mountain Resort (1 mile), Killington Resort (18 miles), Bromley Mountain Ski Resort (23 miles), Stratton Mountain Resort (28 miles), Mount Snow (41 miles) HIKING & LEAF-PEEPING: Buttermilk Falls (3 miles), Healdville Trail (6 miles), Okemo State Forest (7 miles), Coolidge State Forest (12 miles) AIRPORT: Rutland Southern Vermont Regional Airport (19 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 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 - NOTE: This 2-story home requires 3 small steps to enter and interior stairs to reach all bedrooms located on the 2nd floor - NOTE: The window A/C units are seasonal and will only be available during the summer months. During the winter, this property does not offer A/C

Dog-friendly house near Okemo Mountain Resort, skiing, & heart of Ludlow Village

Ludlow, VT, US
3 Bedrooms 8 Guests
Aug 25 - 27
$235 night

With a contemporary and spacious interior dressed in glossy wood accents, comfortable furniture, and lots of natural light, this family-friendly home will make the perfect setting to create plenty of happy vacation memories. This home is less than two miles from Okemo Mountain Resort, where you’ll find over 100 trails for every ski level, while also boasting private or group lessons for kids, mountain coaster plus mountain biking, and concerts in summer. You’ll find plenty of great places to hike, bike, swim, and fish at Okemo State Forest, Plymouth State Park, Buttermilk Falls, and Healdville Trail, all six miles or less away. There are brand new mountain bike trails only 1/2 mile away. Casa Okemo is approximately two miles away from some of Vermont’s best golf at Fox Run Golf Club. Fox Run boasts a challenging 18-hole championship course, a driving range, a kid-friendly mini-course, a golf simulator, upscale dining with entertainment, and more. In the height of fall foliage, Casa Okemo will be your perfect home base to tackle the antique trail, ride the “leaf peeper” train from Chester, and explore Vermont’s famed covered bridges, brew pubs, and wineries. For even more fun, go see the Weston Theater Company that’s only 11 miles away. For more breathtaking sights, Stratton Mountain is 28 miles away. After a day at Okemo Mountain Resort or exploring the area’s boutiques and spas, return to a vacation home featuring the modern touches you crave with a cozy cabin feel. Settle in and thaw out in front of the wood-burning fireplace with a good book and a glass of wine while watching the kids race down the sledding hill out back. The well-equipped kitchen is stocked with an abundance of chef’s tools, perfect for preparing your next crowd-pleasing masterpiece. Your group will love swapping stories about the day’s adventures around the wooden dining table. Don’t feel like cooking? Meander down the neighborhood’s tree-lined streets to all the restaurants and pubs Ludlow has to offer. The fun continues in the warmer months on Casa Okemo’s spacious back patio. Watch the kids romp around in the yard while barbecuing and then gather the group around the firepit for s’mores and stargazing. Things to Know Check-in time: 4:00 PM Check-out time: 10:00 AM All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM No smoking is permitted anywhere on the premises. Please note that the top bunks are only recommended for 180 lbs. or less.

Mountain-view condo with skiing nearby, pool, and balcony - snowbird-friendly

Ludlow, VT, US
3 Bedrooms 7 Guests
Aug 25 - 27
$110 night

Find the ultimate retreat among the mountains of Vermont, a tranquil countryside escape. Only two miles from the lifts of Okemo Mountain Resort, you can experience world-class downhill skiing, or amazing summer activities like hiking, kayaking, and horseback riding. Get rounds of golf in at Fox Run Golf Club, hike up to Buttermilk Falls, or discover exciting local eateries and shops to keep everyone entertained. Upon entry, you’ll be met with a bright interior and a warm feeling of welcome throughout the space. Relax and make yourself at home by resting on the plush furniture, watching movies on the large TV, or curling up with a good book by the warm, crackling fire. If you still have some energy to burn, go for a refreshing dip in the on-site pool. Hobby chefs will love preparing grand meals and on-the-go snacks in the sophisticated galley-style kitchen, equipped with stainless steel appliances and a breakfast bar. Comfortable beds and spacious bedrooms ensure that everyone will receive a restful night’s sleep from the day’s adventures. Enjoy your morning cup of coffee while witnessing the mountain sunrise on the private balcony. Things to Know Check-in time: 4:00 PM Check-out time: 10:00 AM All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM No smoking is permitted anywhere on the premises.

Private Chester Home w/ Deck, Mins to Skiing!

Chester, VT, US
3 Bedrooms 8 Guests
Aug 25 - 28
$419 night

Spacious, private and fully outfitted for a group getaway to Vermont, this 3-bedroom, 3-bath vacation rental is ready for 4 seasons of adventures! Set on 4 private acres with a wraparound deck for summertime relaxation, and a floor-to-ceiling stone fireplace for staying cozy in the winter, this Chester home ensures a stress-free stay. Numerous nearby state parks offer endless hiking and fishing, while Okemo Mountain Resort is under 10 miles away, and Killington is just 32 miles from the home! -- THE PROPERTY -- MRT-11153470-001 | Ping Pong & Foosball | 2,700 Sq Ft | Free WiFi | ~10 Miles to Skiing Ideal for groups of friends and multi-generational families, this expansive home makes an ideal home base for launching mountain adventures and spending time together! Bedroom 1: Queen Bed | Bedroom 2: Twin Bed, Twin/Full Bunk Bed | Bedroom 3: Queen Bed | Living Room: Twin Sleeper Loveseat INDOOR LIVING: Vaulted ceilings, floor-to-ceiling stone fireplace, built-in shelves, 4-person table, laptop-friendly workspace OUTDOOR SPACE: Wraparound deck, Adirondack chairs, wooden porch swing, fire pit, spacious private yard KITCHEN: Fully equipped, stainless steel appliances, 2-person island, microwave, coffee maker, toaster oven, cooking basics, dishware & flatware, blender REC ROOM: Ping pong table, 4-person table, seating area, flat-screen TV w/ Sling Blue Netflix & HBO Go/Now apps, yard access GENERAL: Washer/dryer, iron/board, mudroom w/ ski racks and gear shelving, ceiling fans, suitable for children, suitable for elderly PARKING: Garage (2 vehicles), driveway (3 vehicles) -- THE LOCATION -- WINTER REC: Okemo Mountain Resort (9.9 miles), Killington Ski Area (31.4 miles), Stratton Mountain Resort(29.6 miles), Magic Mountain Ski Area (17.3 miles), Mount Snow Grand Summit Resort (41.1 miles), Bromley Mountain Ski Resort (26.4 miles) SUMMER REC: Fort At No 4 (12.5 miles), Wilgus State Park (16.9 miles), Mt Ascutney State Park (18.0 miles), Killington Ski Area (31.4 miles) ATTRACTIONS: Okemo State Forest (12.8 miles), Buttermil Falls (12.6 miles), Bromley Adventure Park (26.4 miles), Mt Ascutney State Park (18.0 miles), Saint-Gaudens National Historic Park (23.2 miles), Pillsbury State Park (39.1 miles), Mt Sunapee State Park (35.3 miles) DINING: MacLaomainn's Scottish Pub (5.7 miles), the Pizza Stone (5.9 miles), The Hatchery (8.9 miles), Country Girl Diner (5.9 miles), Two Neanderthals Smokin' BBQ (5.5 miles) AIRPORTS: Lebanon Municipal Airport (36.4 miles), Bradley International Airport (120 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 - NOTE: Your safety matters. There is an exterior security camera, facing the driveway and main entrance - Please note all-wheel-drive car may be necessary to drive the 50-yard uphill driveway in the winter - Additional fees and taxes may apply - Photo ID may be required upon check-in - This home's MRT ID # is MRT-11021438 Licence number: MRT-11021438

Secluded Luxury Home on Huge Property with Mountain Views - Near Slopes

Brownsville, VT, US
5 Bedrooms 10 Guests
Aug 25 - 27
$399 night

Tucked away in the peaceful forests of Vermont, this spacious and fully equipped getaway offers the perfect blend of comfort and adventure. With a cozy wood-burning fireplace, multiple inviting living areas, breathtaking mountain views, and space for up to 10 guests, it’s the ideal retreat for a summer escape or a winter ski-cation. Perfectly situated at the base of Mount Ascutney, this vacation home is nestled between the West Windsor Town Forest and the Little Ascutney State Wildlife Management Area—an outdoor lover’s dream! In spring, summer, and fall, take a short stroll to the Bicentennial Trail for scenic hikes and wildlife spotting. Just 1.5 miles away, explore the charm of local history at the West Windsor Historical Society, and don’t miss a scenic drive over the historic Bowers/Brownsville Covered Bridge, built in 1919. For a sweet local treat, visit the Double Diamond Sugar House—only 3.5 miles down the road—for authentic Vermont maple syrup. And when winter rolls in, you’re just 20 miles from the slopes at Okemo Mountain Resort, offering world-class skiing and snowboarding for all skill levels. Inside, you’ll find all the comforts of home—and then some. Enjoy free WiFi throughout, a flatscreen TV with cable, and even a generator to keep things running smoothly no matter the weather. Step outside to an oversized deck and a spacious, grassy yard—perfect for soaking up the views or enjoying outdoor fun with the whole crew. Whip up anything from quick snacks to full family meals in the fully equipped modern kitchen, then gather around the dining table for game night or a cozy dinner. When it’s time to unwind, retreat to the second-floor master suite and indulge in the luxurious jetted tub—ideal after a day of mountain adventures. Whether you’re planning a peaceful getaway or an action-packed escape, this Brownsville gem has everything you need to make unforgettable memories. Why wait? Book your Vermont retreat today! *We recommend 4WD in the winter to access this home.* Meals & Room Tax License #MRT-10082226

Ski-in/out mountainside condo with pool, hot tub, game room & washer/dryer

Ludlow, VT, US
3 Bedrooms 9 Guests
Aug 25 - 27
$153 night

The mountains of beautiful Vermont are calling, and staying at this condo can answer in the best way: a fantastic ski resort getaway. With Solitude lift a mere three-minute walk away with access to green runs, rest assured that you and your loved ones will have an unforgettable vacation when you stay here. Feel your cares melt away in the bubbling hot tub or sauna. Get a workout in the fitness area, or challenge your loved ones to a game of Ping-Pong in the game room. There’s something for everyone here! Upon entry, you’ll be met with a cozy atmosphere and plenty of natural light. Relax and make yourself at home by resting on the plush furniture and streaming your favorite movies on the large TV. Hobby chefs will love creating culinary charms in the sophisticated kitchen equipped with stainless steel appliances, a breakfast bar, and a formal dining table. A dedicated workspace with a desk and chair is provided for those who need to bring work with them. Find the epitome of comfort in any of the bedrooms, which boast en suite bathrooms with walk-in showers. When it isn’t ski season, enjoy all the summer activities and festivals the area offers, such as hiking, biking, kayaking, fishing, and golfing. Lounge about the glittering indoor/outdoor heated on-site pool for much-needed you-time. RESORT AMENITIES -Pools -Hot tub -Sauna -Fitness area -Game room THINGS TO KNOW To use streaming services, guests must log in with their own credentials. The fireplace is not for guest use.

Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Ludlow, VT, US
1 Bedrooms 3 Guests
Aug 25 - 27
$154 night

Wonderfully located in the center of downtown Ludlow, this bright, cozy, first-floor condo gives you unbeatable access to restaurants, gear shops, and the renowned slopes of Okemo Mountain Resort. Ludlow is a small, charming town beloved by outdoor enthusiasts in winter and summer alike. Head across the street, hop on board the shuttle, and spend the day at Okemo Mountain Resort (three-quarters of a mile west) with its 121 trails, 20 lifts, 632 skiable acres of terrain, and 2,200-foot vertical drop - the highest in Southern Vermont. In the summer, you’ll find the Okemo Valley Golf Club, Fox Run Golf Club, Lake Rescue, and Echo Lake all within a couple of miles. After a day spent skiing or hiking at Okemo, Killington, or Stratton, come home to find every comfort waiting for you. Curl up in the living room to watch movies, play board games, and watch the snow pile high outside through the bay window. When you’re not walking out to dinner in town, the well-appointed kitchenette provides every essential for quick and easy meals. As the evening comes to a close, you’ll have a second TV in the bedroom to lull you into a restful night’s sleep. Additional features of the condo include complimentary high-speed WiFi all year round. Things to Know Check-in time: 4:00 PM Check-out time: 10:00 AM All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM No smoking is permitted anywhere on the premises. There is no washer/dryer. Streaming services are available with a guest account. A sleeper sofa provides additional sleeping space.

Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse

Ludlow, VT, US
2 Bedrooms 6 Guests
Aug 27 - 29
$99 night

Welcome to your next ski destination! This ski-in/ski-out home is part of Solitude Village, which is conveniently located on the mountain. When you and your loved ones book this one-of-a-kind escapade you will have access to the Solitude Express quad lift and the Morning Star lift. Additionally, Solitude Village offers a Lodge with incredible shared amenities that will appeal to skiers and non-skiers alike. The Lodge has an indoor/outdoor heated pool, indoor and outdoor hot tubs, fitness center, sauna, locker rooms, and Ping-Pong table. In addition, the Epic restaurant serves lunch during the winter season. This two-bedroom condo is within walking distance of the Solitude clubhouse and less than two miles from the Okemo Mountain Resort. The spacious deck offers impeccable and beautiful views of the valley. The interior boasts a sunny living room with comfortable sofas, a wood-burning fireplace with free wood, and a smart TV with streaming and cable. Prepare delicious treats and homemade meals for the crew in the well-appointed kitchen, which is also complete with a Keurig coffee maker for coffee enthusiasts. And when you want to have a bit of fun, a Wii console and games bring the entire group together. The light-flooded primary bedroom has a large smart TV and an en suite bathroom with a jacuzzi tub. The other guest bedroom also has a smart TV and an en suite bath. Additional amenities include an outdoor closet for skis. SOLITUDE VILLAGE AMENITIES -Indoor/outdoor heated pool -Indoor and outdoor hot tubs -Fitness center -Sauna -Locker room -Ping-Pong table THINGS TO KNOW

Elegantly Rustic Getaway w/Yard, Fire Pit, Dock, Kayaks - Close to Skiing

Ludlow, VT, US
4 Bedrooms 8 Guests
Sep 8 - 10
$309 night

This lakeside retreat is the perfect spot for both summer and winter getaways, offering four spacious bedrooms and plenty of room for up to 8 guests. Whether you’re looking to unwind by the water or hit the slopes, this home offers a comfortable and well-equipped space for all kinds of activities. Summer Fun on Lake Rescue The property boasts a private dock, kayaks, and a canoe, allowing guests to enjoy the tranquility of the lake through swimming, fishing, or leisurely paddling. With a large deck and a gas grill overlooking the water, you can dine al fresco or just relax while enjoying the stunning views. The outdoor firepit with Adirondack chairs makes it easy to unwind at the end of the day with s’mores or just stargazing. Winter Adventures at Okemo For winter enthusiasts, the home can be your ground zero for Vermont’s VAST system of snowmobiling trails, your front row seat to take part in the area’s ice fishing adventures or a convenient hub from which you may hop a few miles over to Okemo Mountain where you can enjoy skiing, snowboarding, or tubing. When the snow melts, Okemo transforms into a hub for mountain biking, golfing, and the Timber Ripper Mountain Coaster—ensuring there’s fun to be had all year round. Comfort and Convenience The home features a modern kitchen that’s perfect for family meals, two family rooms, two cable TVs, and a Ping-Pong table for hours of entertainment. The large dining table is ideal for board games or working on a puzzle. For those who like to stay active, there’s also a Peloton bike available for use with your personal membership. Relaxation and Scenic Beauty With stunning views of the lake and surrounding mountains, the secluded setting ensures a peaceful getaway, while still being close to downtown Ludlow for dining, shopping, and entertainment. Whether you’re inside warming up by the stone fireplace or out on the water, you’ll feel at home in this elegant yet rustic retreat. Book Your Stay Today Perfect for a large family or a few couples looking for a getaway, this home offers all the amenities and activities you could need for a memorable vacation. Make your reservation today for a lakeside retreat that’s both a summer paradise and a winter wonderland! Meals & Room Tax License #MRT-10082226

Beautiful house w/ mountain view, balcony, grill, central a/c, close to skiing

Ludlow, VT, US
1 Bedrooms 5 Guests
Aug 25 - 27
$247 night

Welcome to your newly built, family-friendly retreat in Ludlow, VT! This stunning three-level house offers breathtaking mountain and ski views of Okemo, making it the perfect getaway for outdoor enthusiasts and families alike. With a spacious layout featuring a king bed in the master bedroom, a loft with two twin beds, and a queen sofa bed in the living room, this home comfortably accommodates everyone. Enjoy the convenience of two full bathrooms, ensuring ample space for all guests. Just a short 1/4 mile walk to the entrance of Okemo Mountain, you’ll have easy access to skiing and snowboarding adventures. For those looking to explore further, Killington Resort is only a 24-minute drive away. The property also features a convenient free shuttle pick-up located on High Street, making your travel to the slopes a breeze. Inside, you’ll find modern amenities including central air conditioning, a fully equipped kitchen, and a washer and dryer for your convenience. Step out onto the balcony to enjoy outdoor dining with a gas Blackstone grill while soaking in the stunning mountain views. The living area is perfect for family gatherings, complete with a TV and a selection of board games for cozy nights in. Whether you’re here for skiing, hiking, or simply to relax amidst nature, this Ludlow home is the ideal base for your adventures. Book your stay today and create unforgettable memories in the heart of Vermont!

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