
Holiday rentals with a pool in Stratton
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Stratton

Total holiday rentals
Explore 50 holiday rentals in Stratton

Nightly prices starting at
Stratton holiday rentals start at €61 per night before taxes and fees

Verified guest reviews
Over 1,720 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Stratton holiday rentals include wifi 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!
Top-rated rentals with a pool in Stratton
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Beautiful Bromley/Manchester VT Retreat w/hot tub
"Manchester Moose!" Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Beautifully remodeled VT vacation getaway nestled in the Green Mountains. Closest skiing to quaint Manchester VT, minutes from snowmobiling, hiking, fine dining and shopping. This home features 5 bedrooms, 3 with queen beds including 2 Masters, and 2 bedrooms with double bunks. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains! YouTube video link @GreenMountainStay
4.9 out of 5 average rating, 183 reviews
~10% OFF~Walk To Mountain~Amenities
⭐️"Beautiful place in a great location - recently renovated, super clean and across the street from town." ⇒ Center of Stratton Village, walking distance to restaurants, shops, and the lifts🚶♂️🏔 ⇒ Private balcony with amazing views 🌅 ⇒ Dedicated workspace 📝 ⇒ Gas fireplace 🔥 ⇒ Fully equipped Chef's kitchen👩🍳 ⇒ Central AC/Heat ⇒ Onsite garage parking for 1 vehicle 🅿️ ⇒ Community amenities: pools, hot tubs, sauna, fitness center, tennis court, hiking trail, washer/dryer ⇒ 67 mbps Wifi
4.88 out of 5 average rating, 111 reviews
Slopeside @ Seasons on Mount Snow (Ski-In/Out)
⌲ Escape to Seasons on Mount Snow & stay in our fully equipped 3 bedroom condo where you can you can ski-in & out directly from the condo building! ⌲ Enjoy the log burning fire (wood provided), smart TV & boardgames plus the fabulous Seasons on Mount Snow facilities which include a gym, pool, hot tub, sauna & fire pit. ⌲ Spring thru fall activities in the area include hiking, biking, tennis & pickleball (at Seasons), scenic rides, lakes, golf, camp, spa & enjoying the stunning fall colors.
4.92 out of 5 average rating, 105 reviews
Base of M.S. All Seasons Fun. Deck/HotT/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.
4.92 out of 5 average rating, 128 reviews
4BR Ski Chalet | Hot Tub | Mins to Stratton, VT
Situated at the edge of protected forest land,this stay is a match for those who are seeking privacy to get away from the chaos of urban life and to decompress.How ? Enjoy the private and heated pool(until Sep15) during the day,and hang out by the outdoor fire pit when the sun is setting,and finish your evening off at the enclosed and brand new sea-salt hot tub!You will smell changes in the air as you drive through the trees,and you will hear the birds instead of the sirens when you are here.
4.89 out of 5 average rating, 135 reviews
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.
5.0 out of 5 average rating, 137 reviews
Moon Valley Country Retreat no clean fee pets yes
Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.
4.91 out of 5 average rating, 1025 reviews
Modern Cottage between Stratton and Mount Snow VT
Escape to a Charming, newly Remodeled Chalet nestled perfectly between Mount Snow and Stratton,this cozy retreat is your ideal getaway—whether you're seeking outdoor adventure or quiet relaxation. Beautifully updated and full of charm, the chalet offers a peaceful setting with easy access to hiking, skiing, and everything Southern Vermont has to offer. Calendar Tip: If your preferred dates appear unavailable, feel free to reach out! The calendar typically opens just 2–3 months in advance.
4.97 out of 5 average rating, 113 reviews
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.
4.97 out of 5 average rating, 214 reviews
Log Cabin Near Stratton/Mt Snow
Rustic log cabin for those looking for a getaway and a real Vermont experience. Pets allowed with *PET FEE* - add to your reservation There is Wifi &cell service (AT&T, Verizon). Please be aware this is not a luxury cabin, it is an authentic log cabin that we enjoy as a family during all seasons. No cable television - there is a TV with a Chromecast that you can use to stream from your phone over wifi. Firewood not provided 20 minutes to Stratton and 15 minutes to Mt. Snow
4.79 out of 5 average rating, 279 reviews
Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow
Large Log cabin home located midway between Stratton Mountain and Mt Snow and near the town of Dover. There is plenty of space for you and your nearest and dearest in this 4 bed/4 bath home. Whether you are entertaining friends and family in the open-concept living and dining space, quietly curled up with a book in front of the cathedral fireplace, or enjoying a relaxing soak in the outdoor hot tub after a long day on the slopes—this place has something for everybody!
4.9 out of 5 average rating, 250 reviews
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. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.
4.88 out of 5 average rating, 262 reviewsPopular amenities for Stratton rentals with a pool
House rentals with a pool

Luxury Mid-Century Modern Vermont Home, Okemo View
4.99 out of 5 average rating, 100 reviews
Historic Farm Stay | Heated Pool + Hot Tub
4.98 out of 5 average rating, 214 reviews
Family-friendly 4BR | Pools Hot Tub | Near Mt Snow
4.89 out of 5 average rating, 183 reviews
Hollywood Bungalow in the Berkshires #C0191633410
4.9 out of 5 average rating, 241 reviews
The 1770 House
4.9 out of 5 average rating, 144 reviews
Ski Mountain View Estate
4.96 out of 5 average rating, 142 reviews
The Vermont Barn (Mount Snow)
4.84 out of 5 average rating, 183 reviews
Stratton ski/walk on/off, King beds, FP, Hot tub
5.0 out of 5 average rating, 7 reviewsApartment rentals with a pool

Walk to Mt. Snow-Spa-Summer Pool
4.86 out of 5 average rating, 146 reviews
Great Amenities-Season Condo gym-sport center-pool
4.94 out of 5 average rating, 107 reviews
MountSnow ski on/off condo in Vermont
4.93 out of 5 average rating, 113 reviews
Mount Snow Ski Chalet
4.85 out of 5 average rating, 117 reviews
Okemo Ski Condo, Steps from Trails. Modern & Cozy
4.94 out of 5 average rating, 106 reviews
Mtn. view, easy access to village
4.92 out of 5 average rating, 26 reviews
Your Vermondo awaits: Steps to Lifts & Village.
5.0 out of 5 average rating, 61 reviews
Walk to lifts & Village,Year round pool&hot tubs
4.99 out of 5 average rating, 92 reviewsOther holiday rentals with a pool

Vermont Vacation Villa—Grapevine Getaway
4.95 out of 5 average rating, 100 reviews
Renovated Long Trail 1 Bedroom
4.97 out of 5 average rating, 34 reviews
Ski In / Ski Out 4BR / 3BA Private Hot Tub and sha
4.78 out of 5 average rating, 54 reviews
Slopeside Haven with pool access!
4.93 out of 5 average rating, 28 reviews
Summit’s Stratton Sneak Away II
4.91 out of 5 average rating, 32 reviews
Sheldon Hill Chalet | 4BR Home by Mt Snow/Stratton
4.96 out of 5 average rating, 54 reviews
Bright 3B/2.5B Stratton Condo- Amazing location!
4.88 out of 5 average rating, 26 reviews
Beautiful, Bright, Cozy 3-Bedroom Townhouse
5.0 out of 5 average rating, 14 reviewsWhen is the best time to visit Stratton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €598 | €716 | €480 | €380 | €216 | €229 | €272 | €275 | €258 | €270 | €325 | €544 |
| 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 |
Destinations to explore
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- Rentals with a hot tub Stratton
- Rentals with pools Windham County
- Rentals with pools Vermont
- Rentals with pools United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- June Farms
- Monadnock State Park
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- West Mountain Ski Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Killington Resort
- Rensselaer Polytechnic Institute
- Mount Monadnock
- Emerald Lake State Park
- Bromley Mountain Ski Resort
- Saratoga Spa State Park
- University of Massachusetts Amherst
- Massachusetts Museum of Contemporary Art
- Mount Sunapee Resort
- Mount Greylock
- National Museum of Racing and Hall of Fame





