
Vacation rentals with a pool in Stratton
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Stratton
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Secluded Luxury Lodge On Stratton w/ Heated Pool
Escape to nature at the luxurious Whispering Pines Lodge, a private retreat with high-tech conveniences, a hot tub, sauna, incredible views and just minutes to Stratton. Highlights include: -Stunning panoramic mountain views from every room -Spacious lodge layout designed for families and groups -Entertainment amenities for all ages, in every season -Cozy nooks and gathering spaces for relaxation -Expansive wrap-around porch to enjoy nature year-round Whispering Pines Lodge is more than a

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)
Escape to Seasons on Mount Snow & stay in our fully equipped 2 bedroom (ski in/out) condo. Our location is the best on the mountain ... right between the main face & Carinthia Freestyle Park! Enjoy the log burning fire (wood provided), smart TV & boardgames plus the fabulous Seasons on Mount Snow facilities where you can relax in a hot tub, pool or sauna. See below for info on activities in the warmer months including hiking, biking, scenic rides, lakes, golf, camp, a spa & the fall colors!

Walk to Mt. Snow-Spa-Summer Pool
*Exterior construction on siding until end of Feb *Amenity rich studio only a 5 min walk to Mt. Snow's famed Magic Carpet (runs on weekends) *Gas Fireplace *Queen memory foam Murphy bed *Queen pull out with memory foam mattress *Well appointed kitchen *65" curved UHD TV *25Mbps Wifi *USB wall outlets *Blue tooth music streaming to TV *Ample closet space *Patio with rocking chair *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna
Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

Mid-mod VT Dream Chalet near skiing, lake & forest
Surround yourself in nature and cozy modern comfort. The romantic mid-mod-styled chalet backs to 10 acres of peaceful forest yet is just 12 min drive to Mount Snow for great skiing. 3 min. to the boat launch of gorgeous Lake Whitingham where you can rent jetskis & boats or go swimming & fishing. Hike trails to the charming town of Wilmington with its coffee shops & restaurants. Pools & hot tub up the road at clubhouse. Just steps away from iceskating, pickleball, hiking & snowmobile trails.

Premier Stratton Village Location - Pool & Hot Tub
-- Walk across the street to Stratton Ski Lifts -- Conveniently located near the Stratton Village, this condo places you at the center of all the mountain activities - skiing, mountain biking, events, weddings, shopping & dining. This updated studio includes gas fireplace, AC, stainless appliances, and nice décor. Long Trail House condos boasts underground heated parking, year-round outdoor pool with patio and multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

Cozy Vermont Antique Sugar House with Fireplace
Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

MountSnow ski on/off condo in Vermont
Ski seasons just began Pool and Sports Center is open. Hours vary by day BBQ available for use by the outdoor pool pavilion On Mount Snow, Across from the Tin Lizzy trail leading to the Sundance Base Lodge and access to the Seasons Pass trail leading back to the condo. Very unique Condo in seasons as it has high vaulted ceilings. Condo is a 2 bedroom, 2 bathroom with 2nd bedroom on 2nd floor. Plenty of tennis and pickleball courts Best parking on the mountain

Mt Snow Ski In/Out at Seasons
Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. Free parking. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

Bear's Den - Mt Snow Townhome w/ Ski Home Trail!
Renovated 3-level, 2 bedroom+ twin sleep loft, 2.5 bathroom townhouse on Mt Snow. For the non-snowy months, enjoy the outdoor heated pool, gas fire pit, grill, tennis courts & hiking trails up the mountain as well as other great local activities, lakes and festivals near by. In the winter, take the shuttle 1 mile to the mountain and take the private ski trail back home. NOTE: Pool is Open between Memorial Day & Labor Day

Winter Dream! The Handle Lodge at Snowtree Condos
The Handle Lodge at Snowtree Condos is a modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with friends and family. Make a meal in the beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge.

Mt Snow Chalet: Peaceful Escape w/Hot Tub
Escape to the serene beauty of Vermont's Green Mountains at the Mount Snow Chalet, a charming retreat nestled on a private wooded lot in the desirable Chimney Hill community of Wilmington. 🏠🌳 Just minutes from the slopes of Mount Snow, our chalet offers the perfect blend of rustic charm and modern amenities for an unforgettable getaway. Designed with love and care, we invite you to relax and stay awhile! 🥰
Popular amenities for Stratton rentals with a pool
House rentals with a pool

Stratton/Mt Snow minutes away! Hot tub + Game room

Magical Farm Getaway - a must visit!

Adams Farm-"The Little Farmhouse"

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Winter Skiing @ Mt Snow! Ski off trail sleeps 8.

Wander In | Close to Mount Snow & Stratton

Historic 1850’s Renovated Farmhouse w/ Pool!

Hollywood Bungalow in the Berkshires #C0191633410
Condo rentals with a pool

Walk to lifts & Village,Year round pool&hot tubs

Mount Snow Ski Chalet

Slopes N Seasons | Trailside Condo at Mount Snow

Renovated Condo - 5 min walk to Mount Snow

Cozy Bromley Retreat

Ski On/Off 2BR w/Pool, Fireplace & Arcade

One Bedroom Suite Near Okemo

1st Fl Condo 3BR @ Stratton Sleeps 7 Pool, Hot Tub
Other vacation rentals with a pool

Ski-In/Ski-Out Hike Okemo Condo Solitude Village

Stratton walk on/off, King beds, FP, hot tub, pool

Cozy Bear- 1 mile to Mt Snow Ski Home

Mount Snow Best View - Sauna|HotTub|Pool|Fireplace

Modern Cottage between Stratton and Mount Snow VT

Perfect getaway @ Mt. Snow!

Luxury Mid-Century Modern Vermont Home, Okemo View

Classic Rustic Mount Snow/Stratton Ski Cabin
When is the best time to visit Stratton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ2,622 | ﺩ.ﺇ2,435 | ﺩ.ﺇ1,851 | ﺩ.ﺇ1,293 | ﺩ.ﺇ1,036 | ﺩ.ﺇ1,091 | ﺩ.ﺇ1,146 | ﺩ.ﺇ1,161 | ﺩ.ﺇ1,087 | ﺩ.ﺇ914 | ﺩ.ﺇ1,080 | ﺩ.ﺇ1,950 |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about vacation rentals with a pool in Stratton

Total vacation rentals
Explore 60 vacation rentals in Stratton

Nightly prices starting at
Stratton vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 1,490 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Stratton vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Stratton rentals

4.8 Average rating
Stratton stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with pools Windham County
- Rentals with pools Vermont
- Rentals with pools United States
- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Saratoga Spa State Park
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Willard Mountain
- Fox Run Golf Club
- National Museum of Racing and Hall of Fame
- Hancock Shaker Village
- Mount Sunapee Resort
- University of Massachusetts Amherst
- Rensselaer Polytechnic Institute




