
Holiday 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.

Walk to Mt. Snow-Spa-Summer Pool
*Exterior construction on siding until end of May *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

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

No Cleaning Fee~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

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.

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.

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.

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”.

Hollywood Bungalow in the Berkshires #C0191633410
Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

Beautiful rustic woods and fields retreat.
Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment/ mini house. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $50 per trip per dog

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.

Cozy condo within walking distance to the slopes.
Cozy condo within walking distance of the slopes and restaurants and shops at Stratton Mountain Village. After a day on the slopes relax in the hot tub or take a dip in the heated pool or maybe enjoy some time in the sauna. Then enjoy sitting in front of the gas fireplace and maybe watch a movie. TV is a smart TV, basic cable is included - personal password needed for Netflix, Hulu, etc.
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!

The 1770 House

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

Adams Farm-"The Little Farmhouse"

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Stratton ski/walk on/off, King beds, FP, Hot tub

Historic Home on 17 acres of land. Go escape!
Apartment rentals with a pool

Stratton Long Trail House: Quick Walk to Lifts!

Mount Snow Ski Chalet

Slopes N Seasons | Trailside Condo at Mount Snow

Ski in-out Seasons Condo on mtn-sports center-pool

Four Seasons Slope-side Getaway at Mount Snow

Mtn. view, easy access to village

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck

Stratton Duplex Condo Steps to Lifts, Village!
Other holiday rentals with a pool

Mt Snow 2 Bdrm Condo - Free Ski Shuttle

Quiet Retreat w/Pool/Near Saratoga /Lake George

Idyllic Dorset Home: Serene Escape w/amazing views

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

Bear Tracks Cabin - VT Escape

Slopeside Haven with pool access!

Extraordinary Stratton Ski On/Ski Off Home

Bright 3B/2.5B Stratton Condo- Amazing location!
When is the best time to visit Stratton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $923 SGD | $857 SGD | $651 SGD | $455 SGD | $364 SGD | $384 SGD | $403 SGD | $408 SGD | $382 SGD | $401 SGD | $482 SGD | $806 SGD |
| 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 holiday rentals with a pool in Stratton

Total holiday rentals
Explore 60 holiday rentals in Stratton

Nightly prices starting at
Stratton holiday rentals start at $90 SGD per night before taxes and fees

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

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

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 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!
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- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- West Mountain Ski Resort
- Bousquet Mountain Ski Area
- Saratoga Spa State Park
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- June Farms
- National Museum of Racing and Hall of Fame
- Hancock Shaker Village
- Emerald Lake State Park
- Mount Sunapee Resort
- Congress Park




