
House holiday rentals in Whitingham
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Top-rated house rentals in Whitingham
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Wilmington A-Frame- Cozy and Convenient
Entire charming and chic A-frame chalet conveniently located to all the amenities Wilmington has to offer. Walk into town to enjoy dining, shopping and trail hiking or take a short 15 minute drive to Mount Snow for a day of outdoor adventure. Relax on the water at Harriman Reservoir, just a 2 mile drive from the house. House is also conveniently located along the Moover route. Relax back at the house while enjoying time on the front porch or an evening on the couch. Located on Main Street.

Modern Spacious Home with Mountain Views
Modern Home in Brattleboro with mountain view & many extras: Italian-Marble master-suite, Jacuzzi/Shower for 2, walk-in closet, king bed, grill, heated garage, cable, WiFi. Open-concept living room w/ cathedral ceiling, office, & movie screen. Large open kitchen w/ wine fridge. Second bedroom w/ loft. Explore hiking trails from backyard. Pets ok! 3 mins from Vermont Country Deli & I91 Exit 2. Walking distance to dog park, swimming holes. Downtown: 4 mins Mount Snow: 40 mins Stratton: 54 mins

Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Adams Farm-"The Little Farmhouse"
A Clean Ranch style home with hardwood floors located on a 100-acre Historic Vermont Farm. Retired farmers live in separate farmhouse & are available throughout your stay. Conveniently located just minutes away from MT Snow Ski Resort, Hermitage Resort, Stratton Mt. for Skiing, Snowboarding, Tubing, Hiking & Mountain Biking. 3 miles from downtown Wilmington. Minutes to public beaches and lakes. Use our trails for snowshoeing, X-Country Skiing or hiking. Our Pool is avail July -Labor day

Country Colonial Home with rolling fields & stream
This wonderful colonial home offers wide open space on 21 acres of rolling fields with paths leading to the Green River. In the summer build your own dam or in the winter cross country ski along the edges of the stream and get a full view of the West Arlington valley. Swearing Hill is located within a mile of an old country store for all types of immediate supplies. The town of Arlington is 5 miles away, and Manchester, Vt. Is 14 miles, offering golfing, shopping, and wonderful restaurants.

Vermont lake house near Mt. Snow-fab 360 views!
Welcome to our fabulous farmhouse on 3 green acres! Enjoy amazing views of Lake Sadawga and the surrounding Green Mountains as you kick back in our cozy stylishly furnished home. The house comfortably sleeps 8+ with 4 bedrooms, 2 full bathrooms, and a finished loft space. We are located off the beaten path on a paved road with multi-car parking. This wonderful year-round retreat is a short drive to skiing at Mt. Snow, boating in Harriman Reservoir, and easily accessible to local amenities.

Berkshire Mountain retreat with Urban eco-luxuries
600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

The Vermont Farmhouse|Hiking|Dog Trails|Village
Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Peaceful cabin close to skiing & Brattleboro
Country privacy close to the best of Southern VT! This spacious home is close to skiing (20 min to Mt. Snow; 35 min to Stratton), river swimming holes, hiking, biking, art galleries and great restaurants. Open concept with fireplace, cook's kitchen, jet bathtub, gardens, winter hot tub off deck, and large patio and fire pit give the perfect vibes for your VT gathering. Secluded from neighbors but close to amenities, this home is a comfortable and peaceful retreat.

The Gate House--Experience Vermont!
The Gate House is a historic property located at the foothills of Mt Anthony. Built in 1865, the original structure of the house served as the gate house to the Colgate Estate, one of the most beautiful properties in Southwestern Vermont. Our home is just a few short miles to downtown where you can find local restaurants and breweries. We are not far from some of the best skiing/riding in the Northeast at Mt Snow, Bromley, Stratton and Prospect Mountains.

Cozy Modern Sugar House with spectacular views.
This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Stunning mid-century house on 2.5 private acres
Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.
Popular amenities for house rentals in Whitingham
House rentals with a pool

Magical Farm Getaway - a must visit!

The 1770 House

Berkshire Mountain House

The Villa - Farmhouse with Hot Tub, Pool and Pond

Serene South Deerfield Retreat

Beautiful family friendly home with views & pool!

Chimney Hill Home w/ New Hot Tub & Amenity Center!

Hollywood Bungalow in the Berkshires #C0191633410
Weekly house rentals

Mt Snow Ski Home Sleeps 13 with EV Charger Hot Tub

Tall Pines Rental | Pet Friendly | Fire Pit | Yard

*NEW* Modern VT Ski Cabin w/ Vinyl Listening Loft

Beautiful Jacksonville home- pond/mountain views

VT Outdoor Retreat-Fire Pit-Yard Games-Sleeps 11

Stonehedge Farm family getaway - swim, ski, hike

Charlemont Chalet - A 15 Acre Private Retreat

“Heaven on the Hill” Lake view from every room
Private house rentals

Cozy cottage on peaceful pond

Stratton Summer House | Trails + Swim Holes + AC

Vermont Village Retreat Near Mount Snow

Stone Ridge Cottage

Relaxing Mountain Retreat with a View

Mountaintop Views, near Private Schools, ski/golf

Secluded cabin on brook near skiing and lakes

A-Frame | Hot Tub| Dog Friendly | Near Mt. Snow
Destinations to explore
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- Pet-friendly rentals Whitingham
- Rentals with a firepit Whitingham
- Rentals with a fireplace Whitingham
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- Rentals with a patio Whitingham
- Family-friendly rentals Whitingham
- House rentals Windham County
- House rentals Vermont
- House rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Butternut Ski Area and Tubing Center
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- June Farms
- Fox Run Golf Club
- Saratoga Spa State Park
- Bromley Mountain Ski Resort
- Naumkeag
- Norman Rockwell Museum
- National Museum of Racing and Hall of Fame
- Berkshire Botanical Garden
- New York State Museum
- Emerald Lake State Park
- Hancock Shaker Village
- Rensselaer Polytechnic Institute





