
Vacation rentals with a pool in Brattleboro
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Top-rated rentals with a pool in Brattleboro
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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.

Rocky Ledge at Highland Lake: Cozy 3BR Log Cabin
Nestled within the woods of Stoddard, NH, Rocky Ledge is a peaceful year-round family retreat. Our cozy log cabin has 3 bedrooms, 2 bathrooms, and a lower-level den perfect for family time. Enjoy outdoor dining on the large 3-sided deck, and cap off your days with s'mores sessions at the fire pit! Boating, hiking, swimming, and skiing are minutes away. Or, get cozy indoors and enjoy movies, puzzles, and games. Rocky Ledge is pet-friendly! We welcome up to two dogs with a flat $50 pet fee.

The 1770 House
Come and enjoy our country retreat with breathtaking mountain and valley views. This expanded 1770 farmhouse gives you 4,500 sq. ft. of space for large family and friend get togethers. The house overlooks the Green River Valley with views to Vermont. The end of a dirt road location provides an escape with views that are changing through the seasons. There are six bedrooms and three bathrooms. Have an event or special gathering from wedding to retirement let us know maybe we can help.

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”.

The Brick House on Washington Street
Three guest bedrooms in a Colonial home on Washington Street make a great launchpad for visitors to Keene. From here, it's a pleasant walk or drive to Downtown restaurants, the theatre and shops. The Sterling family has owned this pretty place since 1982 and a design studio operates in the barn portion of the space. The open living room with TV and original fireplace adjoin a "tea room" with a bright bay window. Family chef-approved, guests are welcome to use the spacious kitchen.

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

Perfect Base for Your Berkshire Adventure
Charming private guesthouse with shared pool use. Newly renovated, the space features high ceilings, queen sized bed, rustic Arts & Crafts furniture, heat/air conditioning, and kitchenette. Located in an outbuilding on the property, the guesthouse is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3 - 5.
Popular amenities for Brattleboro rentals with a pool
House rentals with a pool

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

Private chalet | hot tub, shuttle & ski home trail

Adams Farm-"The Little Farmhouse"

Serene South Deerfield Retreat

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Mountain Blossom Retreat by Evergreen Home

Woodsy Retreat with Private Pool

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

Mount Snow Ski Chalet

Slopes N Seasons | Trailside Condo at Mount Snow

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

No Cleaning Fee~10% OFF~Walk To Mountain~Amenities

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

One Bedroom Suite Near Okemo

A Village location, Steps to the Lifts & Village

Cozy condo within walking distance to the slopes.
Other vacation rentals with a pool

Berkshire Mountain House

Mt Snow 2 Bdrm Condo - Free Ski Shuttle

Lodge on the Loop: pet-friendly, hot tub & sauna

Vintage BARN Apt-POOL-HotTub-FirePit-Farms-Foliage

Trending Cabin | HotTub • Pool • Near Mount Snow

Mountain Paradise | Hot Tub | Pool | 8min Mt Snow

Luxury Mid-Century Modern Vermont Home, Okemo View

Classic Rustic Mount Snow/Stratton Ski Cabin
Destinations to explore
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- Rentals with a fireplace Brattleboro
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- House rentals Brattleboro
- Rentals with a fire pit Brattleboro
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- Rentals with a patio Brattleboro
- Rentals with pools Windham County
- Rentals with pools Vermont
- Rentals with pools United States
- Stratton Mountain
- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Stratton Mountain Resort
- Mount Sugarloaf State Reservation
- Mount Tom State Reservation
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Dorset Field Club
- The Shattuck Golf Club
- Hooper Golf Course
- Crotched Mountain Ski and Ride
- Northern Cross Vineyard
- Hancock Shaker Village
- Brattleboro Ski Hill
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Ekwanok Country Club