Windham Area Rentals
From $400 per night (USD)VRBO
Private dog-friendly house w/ mountain views, fireplace, deck, firepit, w/d
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled between the Berkshire East Ski Area and Mt. Snow Resort, this dog-friendly 3-bedroom, 2-bathroom house in Whitin ...
From $400 per night (USD)VRBO
From $357 per night (USD)Expedia
Cozy condo w/ golf course views, pet-friendly, balcony, bbq, fireplace, mudroom
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the picturesque town of Wilmington, VT, this welcoming and comfortable townhouse at Spyglass on the Haystack ...
From $357 per night (USD)Expedia
From $642 per night (USD)VRBO
Mountainside resort condo, hot tub, gas fireplace, bus to slope, wifi, w/d
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled on the east side of Stratton Mountain Resort in the charming town of Stratton, VT, this light-filled condo offer ...
From $642 per night (USD)VRBO
From $231 per night (USD)Expedia
Mountain-view condo with private balcony, fireplace, & updated interior
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Enjoy an ideal vantage point close to everything on Stratton Mountain at this Vantage Point condo. Along with convenient ...
From $231 per night (USD)Expedia
From $224 per night (USD)VRBO
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect mountain getaway in Stratton, VT! This charming studio condo, located on the 4th floor, offers b ...
From $224 per night (USD)VRBO
From $168 per night (USD)Expedia
Cozy studio cabin w/ seasonal mountain views, wrap-around deck, window a/c, bbq
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Escape to the serene beauty of Wardsboro, VT, in this charming rustic cabin that offers seasonal mountain views and a we ...
From $168 per night (USD)Expedia
From $535 per night (USD)VRBO
Multi-level resort home near ski resorts with balcony, streaming, W/D
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled between the charming towns of Dover and Wilmington, this inviting condo offers a peaceful retreat for your next ...
From $535 per night (USD)VRBO
From $859 per night (USD)Expedia
Beautiful house w/ mountain & pond views, hot tub, pool table, bbq, firepit, w/d
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this stunning 4-bedroom, 2.5 bathroom dog-friendly house in Windham, VT, offering breathtaking mountain and po ...
From $859 per night (USD)Expedia
From $252 per night (USD)VRBO
Ski-in/ski-out condo w/ deck, wood-burning fireplace, wifi, community amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the ultimate slopeside lifestyle at Mount Snow with this spacious 1-bedroom, 1-bath condo nestled in the desi ...
From $252 per night (USD)VRBO
From $330 per night (USD)Expedia
Cozy log house w/ gas-fire stove, dog-friendly, clubhouse amenities, w/d, wifi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your dog-friendly log home retreat in Wilmington, Vermont! Nestled in the scenic Deerfield Valley, this very ...
From $330 per night (USD)Expedia
From $216 per night (USD)VRBO
Ski-in/ski-out condo w/ wood-burning fireplace, patio, shared bbq, w/d, wifi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Beautiful Glen Run 2S, your perfect ski-in/ski-out retreat located right at the base of Mount Snow's all-terr ...
From $216 per night (USD)VRBO
From $563 per night (USD)Expedia
Cozy house close to Mt Snow w/ hot tub, balcony, bbq, two kitchens, w/d, wifi
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to your perfect getaway in West Dover, Vermont! This spacious duplex house is ideally located just 0.6 miles fro ...
From $563 per night (USD)Expedia
From $331 per night (USD)VRBO
Mountain view condo w/ fireplace, shared hot tub, pool, sauna, tennis & shuttle
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your perfect vacation retreat at Mount Snow Resort in Dover, VT! This freshly renovated condo offers a spacio ...
From $331 per night (USD)VRBO
From $362 per night (USD)Expedia
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The location can't be beat at this trailside condo, located in Seasons, the only ski-in/ski-out community at Mt. Snow! S ...
From $362 per night (USD)Expedia
From $769 per night (USD)VRBO
Cozy upper unit duplex, close to Mt Snow w/ balcony, bbq, fireplace, kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your perfect getaway in Dover, VT! This charming duplex upstairs unit is just a short 0.6-mile walk from the ...
From $769 per night (USD)VRBO
From $167 per night (USD)Expedia
Studio w/ mountain view, shared pool, hot tub, sauna, tennis courts & shuttle
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Welcome to your ideal mountain retreat in Dover, Vermont! Nestled within the Mt. Snow ski resort, this newly renovated s ...
From $167 per night (USD)Expedia
From $345 per night (USD)VRBO
Bright three-level home with water views, jetted tub, firepit, and pool table
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the water views and the rural vibes at this three-level house in Jacksonville! You'll be staying just half a mile ...
From $345 per night (USD)VRBO
From $461 per night (USD)Expedia
Renovated Ski-in/Ski-Out Condo w/ Shared Pools, Hot Tub, Sauna & Great Location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Bring the whole crew to enjoy a bevy of alpine activities at this Mount Snow getaway, a fully renovated and professional ...
From $461 per night (USD)Expedia
From $189 per night (USD)VRBO
Comfortable condo with fireplace, pool, and sauna access - near slopes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your Mountain Escape Awaits at Mt. Snow Resort Welcome to your cozy condo retreat, perfectly positioned at Mt. Snow Res ...
From $189 per night (USD)VRBO
From $722 per night (USD)Expedia
Cozy condo w/ mountain view, fireplace, balcony, shared pool, sauna, & hot tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your perfect mountain retreat in Dover, Vermont! Just a mile from the lifts at Mount Snow, this spacious thre ...
From $722 per night (USD)Expedia
From $344 per night (USD)VRBO
Cozy condo w/ wood-burning fireplace, deck, wifi, w/d, bus route, TVs, cable
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Charming Mountain Retreat in Dover, VT — Your Four-Season Escape! Tucked away in the scenic mountains of Dover, Vermont ...
From $344 per night (USD)VRBO
From $662 per night (USD)Expedia
Cozy lower unit duplex, close to Mt Snow w/ hot tub, fireplace, kitchen, w/d
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your perfect getaway in Dover, VT! This charming downstairs duplex unit is ideally located just 0.6 miles fro ...
From $662 per night (USD)Expedia
From $690 per night (USD)VRBO
Ski-in/ski-out condo w/ deck, wood-burning fireplace, wifi, community amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the heart of West Dover, VT, this trailside condo in Seasons offers the ultimate ski-in/ski-out experience at ...
From $690 per night (USD)VRBO
From $921 per night (USD)Expedia
Gorgeous home near Mount Snow with hot tub, game tables, fireplace, & desk
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This gorgeous all-season home is ready to provide the perfect landing point for an adventure you won't be soon to forget ...
From $921 per night (USD)Expedia
From $633 per night (USD)VRBO
Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
A-Frame | Hot Tub Sauna EV | Stratton 🌲 13 min to Stratton 🎿 <30 min to Magic, Bromley, Okemo & Mt Snow | ~1 hr ...
From $633 per night (USD)VRBO
From $678 per night (USD)Expedia
Fabulous 5-bedroom chalet in charming Wilmington perfect for groups
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Get ready to relax in this 5-bedroom chalet in Wilmington. The space features 3 queen beds, 2 full beds, and a cozy crib ...
From $678 per night (USD)Expedia
From $563 per night (USD)VRBO
Brookenridge Lodge | Near Mt. Snow w/ Fire Place
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Come relax at this beautiful home in Wilmington, VT. Freshly renovated with stylish upgrades, with two living ...
From $563 per night (USD)VRBO
From $1115 per night (USD)Expedia
Meadowview: Private Pool, Hot Tub, Tennis & Pickle
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Meadowview, a private 11-acre estate where modern luxury meets historic farmhouse charm. Ideal for families, ...
From $1115 per night (USD)Expedia
From $242 per night (USD)VRBO
The Studio with a View. Bring your dog, too!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
A private studio designed for relaxation in nature. Gorgeous views for reading or gathering with friends and family. Th ...
From $242 per night (USD)VRBO
From $1532 per night (USD)Expedia
Ski-In/Out Lodge | Stratton Mountain
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: Experience true ski-in/ski-out living at this spacious six-bedroom lodge on Stratton Mountain. Sleeping up to ...
From $1532 per night (USD)Expedia
From $199 per night (USD)VRBO
The Eagles Wing at The CHM - Private Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to The Eagle’s Wing at The Carriage House Manor in West Dover, VT! This is a full Private Apartment, perched at ...
From $199 per night (USD)VRBO
From $409 per night (USD)Expedia
Cozy renovated 3-bedroom house in Wilmington do it all ski, hike, golf, swim
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Make yourself at home in this 3-bedroom Wilmington house. Guests will find three queen beds, a twin bed, and a crib, per ...
From $409 per night (USD)Expedia
From $754 per night (USD)VRBO
The Aster Chalet - a modern family retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to The Aster Chalet! Our mid-century getaway has been thoughtfully updated with modern-day amenitie ...
From $754 per night (USD)VRBO
From $616 per night (USD)VRBO
Derry Woods Cabin: Views | Deck | Lowell Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Derry Woods is a modern 3 bed, 2.5 bath cabin just 3 hrs from Boston & central to Vermont’s skiing, dining, & ...
From $616 per night (USD)VRBO
From $259 per night (USD)VRBO
Spacious Country Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Freshly remodeled country home sits on a quiet, wooded lot with a large deck for summer grilling. The spacious open kitc ...
From $259 per night (USD)VRBO
From $611 per night (USD)VRBO
The Post Haus: one-of-a-kind modern VT experience
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to The Post Haus! A one-of-a kind, modern Vermont mini cabin in the Green Mountain National Forest. Th ...
From $611 per night (USD)VRBO
From $485 per night (USD)VRBO
Crosstown Retreat | 2 Miles to Mt Snow w Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Spacious 3 bedroom plus loft townhome just a 5 minute drive to Mount Snow, near the Valley Trail and Mt Snow G ...
From $485 per night (USD)VRBO
From $813 per night (USD)VRBO
Brand New: Forest Green Retreat in Brattleboro, VT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience luxury and nature at our Forest Green Retreat in Vermont. Set among lush woods, it’s the ideal getaway for ou ...
From $813 per night (USD)VRBO
From $771 per night (USD)VRBO
Spacious 4-BR Retreat Near Stratton & Mt. Snow
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Escape to Southern Vermont in this spacious 4-bedroom retreat just 10 minutes from Stratton and Mount Snow. De ...
From $771 per night (USD)VRBO
From $466 per night (USD)VRBO
Silver Birch Chalet: Mountain Apt w/ Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to The Silver Birch Chalet! A spacious family escape centrally located to dining, shopping, and four V ...
From $466 per night (USD)VRBO
From $374 per night (USD)VRBO
Only at Mt Snow!! Carinthia Slopeside walk on ski off Cannot get much closer!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay comfortably slopeside at this 2-bedroom condo. The space features two queen beds and a cozy living room with a sofa ...
From $374 per night (USD)VRBO
From $541 per night (USD)VRBO
Silver Birch Chalet: 4-bdrm family stay w/ hot tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to The Silver Birch Chalet! A spacious family escape centrally located to dining, shopping, and four V ...
From $541 per night (USD)VRBO
From $406 per night (USD)VRBO
Awesome cozy cabin with amazing views of Mt Snow.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
New for 2026: 2 Zone heating system to keep your warm throughout the cold Vermont winters! Cozy Vermont knotty pine c ...
From $406 per night (USD)VRBO
From $805 per night (USD)Expedia
Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
✔ Barrel sauna ✔ Hot tub ✔ Game room: pool table, shuffleboard ✔ Wood-burning fireplace + outdoor fire pit ✔ Outdoor ha ...
From $805 per night (USD)Expedia
From $473 per night (USD)VRBO
Luxury Stratton Village Condo | Walk to Lifts, Dining & Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hearthstone Lodge is modeled after the Grand National Park lodges of the West and is filled with unique stone and timber ...
From $473 per night (USD)VRBO
From $440 per night (USD)Expedia
Chalet With A/C, 5 minutes from golf and Mount Snow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Bring the whole family to this huge yet cozy house with large sleeping and entertaining spaces just minutes from Mount S ...
From $440 per night (USD)Expedia
From $195 per night (USD)VRBO
Charming 1-bedroom bungalow with AC in Brattleboro
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This charming turn of the century cottage has been mindfully renovated with warm colors and a meditative vibe. The space ...
From $195 per night (USD)VRBO
From $780 per night (USD)VRBO
Walk to Ski Lifts with Perfect Location! 3 Bedroom Townhome plus Loft.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy a 3 level, 3 bedroom plus loft Townhome right in Mount Snow Village. Our Townhome is meticulously cleaned and sani ...
From $780 per night (USD)VRBO
From $1208 per night (USD)VRBO
West Hill Lodge | 6-BR Estate Near Stratton
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Set on 27 private acres in Jamaica, Vermont, West Hill Lodge is a secluded mountain retreat just 8 minutes fro ...
From $1208 per night (USD)VRBO
From $358 per night (USD)Expedia
Vermont Chalet w/ Sweeping Mountain Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
*Monthly and seasonal rentals available. Please inquire directly for rates. Tucked away on a quiet country road, this c ...
From $358 per night (USD)Expedia
From $296 per night (USD)VRBO
Cozy 3 bedroom home in West Dover, VT. Perfect for skiing, hiking, and relaxing.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom home in West Dover features a mix of sleeping options, including a bunk bed, twin beds, and two queen bed ...
From $296 per night (USD)VRBO
From $549 per night (USD)Expedia
Spruce Lake Lodge | Lake Access, Close To Mt Snow!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to The Spruce Lake Lodge! Unwind on a private lakefront retreat surrounded by water and mountain vi ...
From $549 per night (USD)Expedia
From $3037 per night (USD)VRBO
New! Most Luxurious 7BRs Mountain Estate in Vermont, Hot Tub with live waterfall
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 14
The most luxurious mansion in Vermont. Just 15 min from Mt. Snow! This private mountain estate sits on 13 secluded acres ...
From $3037 per night (USD)VRBO
From $390 per night (USD)Expedia
Charming luxury tiny cabin with AC and all the amenities in peaceful Putney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Enjoy an intimate weekend escape in our 400 sq ft Tiny Cabin, located in Southern Vermont! This Home overlooks gorgeous ...
From $390 per night (USD)Expedia
From $658 per night (USD)VRBO
Vermont Retreat , Sits on Haystack Golf course and 8 min from Mt Snow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Brand new to VRBO , Family -friendly 3 bedroom Vermont town house. Located on the first hole of Haystack Golf course and ...
From $658 per night (USD)VRBO
From $240 per night (USD)Expedia
Hike, Bike & Ski! Condo Steps to Mount Snow Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Pet Friendly w/ Fee | 2 Mi to Green Mountain National Forest Just steps away from Mount Snow, this West Dover vacation ...
From $240 per night (USD)Expedia
From $901 per night (USD)VRBO
Authentic VT Chalet, Family Friendly Destination
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
The large chalet is an all-seasons Mt. Snow and Green Mountains destination for families and friends. The chalet is cle ...
From $901 per night (USD)VRBO
From $302 per night (USD)Expedia
Mt. Snow All Season Condo: w/ shared hot tub & pool, ski shuttle, tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to your vacation retreat at Mount Snow Resort, where adventure meets comfort in this unique, newly renovated con ...
From $302 per night (USD)Expedia
From $614 per night (USD)VRBO
Skybarn Vermont | Pool, 100-Mile Views, Historic Barn
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Skybarn! It’s a historic, modernized mountain-top barn. The 100-mile views of 3 states from the backyard are ...
From $614 per night (USD)VRBO
From $461 per night (USD)Expedia
Summit Dreams: Hot Tub + 2 Fireplaces | Sleeps 13
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to Summit Dreams! This spacious retreat in Dover is perfect for family gatherings. I love the open layout - it f ...
From $461 per night (USD)Expedia
From $363 per night (USD)VRBO
Bear Den: Hot Tub + Secluded | Sleeps 8 | Modern
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Bear Den! The private, modern escape tucked away in the Wardsboro woods. It is incredibly secluded, perfect i ...
From $363 per night (USD)VRBO
From $531 per night (USD)Expedia
Total Privacy on 5 acres with Hot Tub, A/C, stream
- Bedrooms:
- 4
- Bathrooms:
- 1
- Sleeps:
- 12
Enjoy the serene setting and beautiful views from this home on over 5 Acres. This charming home features an open floor p ...
From $531 per night (USD)Expedia
From $1119 per night (USD)VRBO
Long Trail House 1 bdrm condo. Seasonal Rental '26-'27 Ski Season, 23k dollars
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sleeps 4 with pullout sleeper sofa in LR, and 1 Bdrm with a king size bed. Located directly across the street from Strat ...
From $1119 per night (USD)VRBO
From $760 per night (USD)Expedia
Stratton 2BR Walk2ALL Sleeps 6 Pool Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hearthstone Lodge is modeled after the Grand National Park lodges of the West and is filled with unique stone and timber ...
From $760 per night (USD)Expedia
From $512 per night (USD)VRBO
Stratton Log Cabin: Pond + Hot Tub + Privacy!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to the rustic Stratton Cabin! Tucked away at the end of a long private driveway, the place features its own pond ...
From $512 per night (USD)VRBO
From $837 per night (USD)VRBO
Weatherhead Hollow Farmstead – Two historic homes on a private Vermont property
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Weatherhead Hollow is a private Vermont farmstead with two historic homes — the 1792 Farmhouse and the Carriage Barn — r ...
From $837 per night (USD)VRBO
From $3995 per night (USD)VRBO
Spacious 4-bedroom house with Game Room in tranquil Dover with AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience Dover like a local in this perfect 4-bedroom house. With 3 bathrooms, including showers and hair dryers, gues ...
From $3995 per night (USD)VRBO
From $848 per night (USD)Expedia
Spacious Vermont Farmhouse | 3 Mi to Mount Snow
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Come Home to Vermont! Escape to a charming farmhouse just 3 miles from Mount Snow. Made for families and friends, this ...
From $848 per night (USD)Expedia
From $438 per night (USD)VRBO
Jamaica Chalet: 3 Kings + Arcade | Starlink
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to this modern chalet in Jamaica! This home is designed for comfort. It is rare to find a rental with THREE King ...
From $438 per night (USD)VRBO
From $551 per night (USD)Expedia
Eagles Nest: Indoor Hot Tub | Sleep 13 | Barn
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to the Eagles Nest! This home is special to me because it used to be an old barn before it was converted into th ...
From $551 per night (USD)Expedia
From $397 per night (USD)VRBO
Slopeside 2-Bedroom Condo w/ Fireplace & Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a true mountain escape at Glen Run Condos, located right at the base of Mount Snow’s Carinthia slopes, provid ...
From $397 per night (USD)VRBO
Click For PricingVRBO
Beautiful Stratton Mountain- Suttle to slopes; walking distance to hill!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Home away from home - close to the slopes!! Stunning 2 bedroom/2 bath condo at Vantage Point on Stratton Mountain. Our c ...
Click For PricingVRBO
From $446 per night (USD)VRBO
A-Frame | Hot Tub| Dog Friendly | Near Mt. Snow
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Alpine A-Frame! Our beautiful mid-century A-frame cabin right down the road from Lake Raponda in Wilmingt ...
From $446 per night (USD)VRBO
From $486 per night (USD)VRBO
Renovated A-Frame Ski & Sauna Retreat + Hot Tub Near Mt Snow + Stratton
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the perfect blend of luxury, comfort, and family-friendly mountain living at this fully renovated A-frame ret ...
From $486 per night (USD)VRBO
From $645 per night (USD)VRBO
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Consider this apartment your home away from home while you visit Whitingham. Located in the historic EJ Roberts Chevy de ...
From $645 per night (USD)VRBO
From $352 per night (USD)VRBO
Stratton Woods · Secluded Vermont Cabin Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Tucked away in the woods of West Wardsboro, this charming cabin is the perfect year-round escape. Minutes from ...
From $352 per night (USD)VRBO
From $305 per night (USD)VRBO
Marvelous 3-bedroom chalet in charming Wilmington
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Enjoy a peaceful stay at this 3-bedroom chalet in Wilmington. The space features a cozy queen bed, a full bed, and two t ...
From $305 per night (USD)VRBO
From $690 per night (USD)VRBO
Wonderful 4-bedroom townhome in quaint Londonderry perfect for families
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Stay comfortably in Londonderry at this 4-bedroom townhome. The space features two cozy twin beds and two queen beds, ma ...
From $690 per night (USD)VRBO
From $388 per night (USD)VRBO
Fabulous 2-bedroom condo in Wilmington perfect for your getaway
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this pleasant condo in Wilmington. With two bedrooms featuring a queen bed and a twin bed, it’s perfect for a ...
From $388 per night (USD)VRBO
From $643 per night (USD)Expedia
Mountain Chalet in delightful Wilmington Vermont
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located 5 miles from Historic Wilmington. This Reimagined Chalet is located in the Wheeler Village neighborhood. Stay co ...
From $643 per night (USD)Expedia
From $347 per night (USD)VRBO
The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your Vermont home away from home! Nestled in the heart of Wardsboro, this cozy 3-bedroom chalet offers the pe ...
From $347 per night (USD)VRBO
From $3625 per night (USD)Expedia
Delightful 7-bedroom house in Stratton perfect for group getaways
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Stay comfortably in Stratton at this superb 7-bedroom house. With 3 king beds, 3 queen beds, and a twin bed, there’s ple ...
From $3625 per night (USD)Expedia
From $486 per night (USD)VRBO
The Manor on the Ridge | Mt Snow 5 Min · Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Steps from Mount Snow Golf Club and set among Vermont's ridgeline, The Manor on the Ridge is a designer mountain home wi ...
From $486 per night (USD)VRBO
From $460 per night (USD)VRBO
Fully equipped Bears Crossing Condo Mt Snow, VT - Swim, Hike, Bike, Golf, Relax
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Trade the crowds for fresh mountain air and wide-open spaces. This beautiful 3 Bedroom / 2 Bath condo is your perfect Fa ...
From $460 per night (USD)VRBO
From $711 per night (USD)VRBO
Shepardson Brookside: VAST+AT Hike | A/C | Brook
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 12
Welcome to this grand log cabin in Stratton! Located at the end of a quiet dead-end road (an old logging trail!), this h ...
From $711 per night (USD)VRBO
From $557 per night (USD)Expedia
Stratton Log Lodge: Hot Tub + Privacy | Sleeps 13
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to the Stratton Log Lodge! This place is special. it’s a true log cabin perched at the top of a hill with a `Gra ...
From $557 per night (USD)Expedia
From $152 per night (USD)VRBO
Cozy House on 2 Acres in the Green Mountains
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
4 Ski Mtns Within 20 Mi | Arcade Table | Forest-View Office | Gig Fiber WiFi | Jacuzzi Tub | Sauna Magic Mountain ski p ...
From $152 per night (USD)VRBO
From $338 per night (USD)Expedia
Valley Trail Riverfront Townhouse with EV Charging 2 miles from Mount Snow
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This newly renovated townhouse is located in the heart of West Dover just 2 miles from Mount Snow. The Valley Trail runs ...
From $338 per night (USD)Expedia
From $468 per night (USD)VRBO
Superb 3-bedroom townhome in charming Wilmington awaits you
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Consider this townhome your home away from home while you visit Wilmington. This peaceful retreat features three bedroom ...
From $468 per night (USD)VRBO
From $645 per night (USD)VRBO
Ski On Ski Off 3-bedroom condo in Slopeside at Stratton for a relaxing getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in Stratton, this condo is a fantastic retreat for families. Out the front door is the ski on ski off path for a ...
From $645 per night (USD)VRBO
From $704 per night (USD)VRBO
Idyllic Vermont Farmhouse
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ames Farm is a true rural retreat featuring a charming, historic Vermont Farmhouse. Built in 1780, and once a local tave ...
From $704 per night (USD)VRBO
From $1046 per night (USD)Expedia
Chalet Belle Neige: Luxury 5br with Hot tub•Fire pit•Pool table•BBQ
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Escape to the ultimate Vermont mountain retreat, just minutes from Mount Snow. Thoughtfully designed for families, group ...
From $1046 per night (USD)Expedia
From $481 per night (USD)VRBO
Peaceful 3-bedroom+loft house perfect for relaxing stays close to Stratton
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Stratton Mountain Gem — Summer Weekly Rental 3 Bedrooms + Loft • 2 Bathrooms • Sleeps 10 • Private, Sprawli ...
From $481 per night (USD)VRBO
From $2257 per night (USD)Expedia
New- 12BR Fall Getaway Foliage, Trails & Mountain Fun
- Bedrooms:
- 8
- Bathrooms:
- 12
- Sleeps:
- 19
The home is thoughtfully arranged as two distinct buildings: The Bunkhouse features all of the bedrooms, a comfortable ...
From $2257 per night (USD)Expedia
From $276 per night (USD)VRBO
Bright, cozy, dog-friendly suburban home, centrally located, off-street parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the unique character of the Brattleboro area from this 1-bedroom, 1-bathroom home. You'll be welcomed into an o ...
From $276 per night (USD)VRBO
From $653 per night (USD)Expedia
Updated 4BR townhome on golf course w/mtn views. Only mins to Mt Snow ski resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Newly renovated Spyglass Village 4-bedroom townhouse, with stunning mountain views and sunsets. Located directly on Hays ...
From $653 per night (USD)Expedia
From $342 per night (USD)VRBO
West Dover Retreat Near Mount Snow, Lakes & Year-Round Adventure-4 bd, 2.5 bath
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Relax in this peaceful West Dover retreat, surrounded by woods and perfectly situated to enjoy all that Southern Vermont ...
From $342 per night (USD)VRBO
From $352 per night (USD)VRBO
Little Cabin, rustic 4 bedroom near Mt. Snow and Berkshire East
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
The Little Cabin is a rustic wood cabin located in beautiful rural Vermont land, and a great deal for a no-frills, idyll ...
From $352 per night (USD)VRBO
From $425 per night (USD)VRBO
Great Snow in a Peaceful Home in Southern VT
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Mountain Glory - Your Winter Dream House Why brave harried airline travel when you can spend a glorious winter in nea ...
From $425 per night (USD)VRBO
From $200 per night (USD)VRBO
Unique and charming guesthouse in Brattleboro, Vermont
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
The Space Welcome to Mahalo Temple Retreat, a peaceful private guesthouse tucked into nature just minutes from downtown ...
From $200 per night (USD)VRBO