
Holiday rentals with a pool in Stratton
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Top-rated rentals with a pool in Stratton
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

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 grill, multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

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.

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”.

4BR Cabin w/ Hot Tub & Pools –15 mins to Mt Snow
Family-friendly cabin in Chimney Hill, just 15 min to Mount Snow & 35 to Stratton! Relax in our 4BR, 2BA home with a hot tub, indoor and outdoor pools, fire pit, clubhouse gym, fully equipped kitchen & cozy living spaces. Sleeps 8 comfortably (King, Queen, Full + trundle, 2 Twins) with a Pack ’n Play for little ones. Perfect for skiing, hiking, or unwinding year-round. Enjoy mountain charm, modern comfort, and easy access to trails, lakes, and Wilmington’s shops & dining.

Chic Chalet | Hot Tub · Clubhouse · Mt. Snow
Escape to The Sugar Maple Chalet, your stylish family retreat in the heart of Wilmington, Vermont. This thoughtfully updated four-bedroom home blends cozy charm with modern comforts—think high-speed Wi-Fi, a private outdoor hot tub, and a fun-filled basement bar and game room. Just a few minutes from local shops, restaurants, ski slopes, and scenic hiking trails. One well-behaved pet is welcome to join the adventure! AC installed when temperatures average above 78 degrees.

Silver Brook Cabin
Waterfront setting in a relaxing, but convenient, location in southeastern Vermont. Photos and captions do the best job of describing our cabin, adjacent brook, and very nearby Green River with its covered bridge and swimming holes. The cabin is 20 minutes from Brattleboro with its many restaurants, shops, movie theater, and galleries. Not only is the immediate area wonderful for swimming, biking, and hiking, you can also simply relax with a good book or two.

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.

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

Walk to Mt. Snow-Spa-Summer Pool
*Amenity rich studio only a 5 minute 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

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.
Popular amenities for Stratton rentals with a pool
House rentals with a pool

Mt. Snow/Stratton Ski Trip! Hot tub and 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

Wander In | Close to Mount Snow & Stratton

Historic 1850’s Renovated Farmhouse w/ Pool!
Apartment rentals with a pool

Mount Snow Ski Chalet

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

Cozy Fall Retreat: 2BR w/Pool, Fireplace & Arcade

True Ski in/Ski out with Pool, Hot tubs & Firepits

Luxury Condo * 3BD/3BA * Fall Foliage

One Bedroom Suite Near Okemo

Your Vermondo awaits: Steps to Lifts & Village.

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

Ski-In/Ski-Out Hike Okemo Mountain Condo

Modern Chalet-private deck/firepit/ clubhouse pool

Dream Catcher Farm

Summit’s Stratton Sneak Away II

Woodsy Retreat with Private Pool

Luxury Mid-Century Modern Vermont Home, Okemo View

Cottage-loft,fireplace,deck,32 acres-The Woodshed

Classic Rustic Mount Snow/Stratton Ski Cabin
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 € 60 per night before taxes and fees
Verified guest reviews
Over 1,390 verified reviews to help you choose
Family-friendly holiday rentals
40 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
4.9 Average rating
Stratton stays are highly rated by guests – averaging 4.9 out of 5!
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Saratoga Spa State Park
- West Mountain Ski Resort
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Pico Mountain Ski Resort
- Lake George Expedition Park
- Peebles Island State Park
- Hildene, The Lincoln Family Home
- Dorset Field Club
- The Shattuck Golf Club
- National Museum of Racing and Hall of Fame
- Bromley Mountain Ski Resort
- Hooper Golf Course