Holiday rentals in Winhall

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Top-rated holiday rentals in Winhall

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Guest favourite

Home in Cavendish

5 out of 5 average rating, 35 reviews

Okemo <12 min Game room~Hot tub~Fire pit~Mtn Views

The Red Ranch is a hop, skip and jump away from Okemo Mountain Ski Resort. < 12 min to Ludlow, Okemo MTN, nearby lakes and VAST trails. This thoughtfully remodeled farmhouse ranch sits on 4 acres, with HOT TUB. Enjoy the peace and tranquility of nature just beyond your front door. Listen to the sounds of nearby streams roaring in the near distance as you sip on your morning coffee from our enormous, covered porch. This home boasts designer touches with serious attention to details throughout.

Superhost

Flat in Pownal

5 out of 5 average rating, 8 reviews

"The Triple Chambers"

This beautiful, spacious, and historic property was formerly the Inn at Oak Hill. It is convenient to Williams College, Williamstown Theater Festival, Clark Art Museum, MassMOCA, FreshGrass Festival, BerkshireStock, Jiminy Peak, Bennington College, VAST snowmobile trails, and many other destinations in southern Vermont and western Massachusetts. Comfortably furnished with modern amenities such as Wi-Fi and satellite TV, our home also surrounds you with beautifully preserved & original features.

Guest favourite

Home in Hoosick Falls

4.91 out of 5 average rating, 11 reviews

Enjoy Fall & Experience Beautiful Changing Colors

Nestled on a private 5 acres lot on the border of NY and Vermont this home is just perfect. Just 30-60 minutes from several ski areas. This charming home has everything you need to relax and enjoy . The night sky perfect for stargazing. Have morning coffee on the deck and watch as deer wander in the fields or the cows across the meadow. Enjoy a quiet evening by the fire after a long day on the slopes or soak in the oversize soaking tub! Stroller, changing table and a pack-n-play included.

Guest favourite

Cabin in Wilmington

5 out of 5 average rating, 67 reviews

Modern Chalet-private deck/firepit/ clubhouse pool

Nestled in the Green Mountains this custom modern chalet is the perfect location for your family vacation! Enjoy the peaceful tranquility, 12 min. from Mt Snow. The private wrap around deck is the place to be for morning sunrise & coffee Located in Chimney Hill, includes outdoor & indoor pool, gym, tennis, basketball cts. Harriman Reservoir & Lake Raponda for kayaking/ swimming & Wilmington restaurants & shopping are close by. The home is pet free & has high speed fiber! Insta @bearlairlodge

Guest favourite

Home in Poultney

4.89 out of 5 average rating, 9 reviews

Snowberry Farm Home Sweet Home

This memorable place is anything but ordinary. Hike the hayfields on the mowed paths! Fish in the Pond and enjoy the peace and quiet of this comfortable and spacious home. Star gazing is on the menu too! One mile to rail trail for bike enthusiasts. This house is very welcoming & well equipped for entertaining family & friends. Room for everyone & extra space for quiet reading & conversation. Cider house, craft breweries, dining options& golf all nearby. Escape Florida or Arizona summer heat!

Guest favourite

Cabin in Plymouth

4.92 out of 5 average rating, 13 reviews

Poppy's Cabin~Dogs~HotTub~FirePlace&Pit~Okemo

Rent a "room" at an inn or rent this private B & B cottage. Romantic Retreat~Rest & relax at this unique tranquil getaway. Exclusive~A Bed & Breakfast Cottage for 2 adults. 1 BR & 2 BA. Rustic charm, generous modern amenities. King bed, 2 bathrooms, fine linens, living/dining area, galley kitchen, fireplace, hot tub, outdoor shower, porch, fire pit, canoe, & dog friendly! Killington&Okemo15minutesWoodstock 30 minutes-Ludlow 10 minutes Overlooks Lake Amherst. Some features are seasonal.

Guest favourite

Villa in Pownal

4.93 out of 5 average rating, 61 reviews

Vermont Vacation Villa—Grapevine Getaway

Nestled in the stunning natural beauty of Vermont, this striking villa offers the perfect escape from the hustle and bustle of everyday life. Surrounded by rolling hills, and picturesque countryside, this home is a paradise. Whether exploring the area's cultural institutions, immersing yourself in the natural beauty of Vermont, or relaxing and unwinding with family and friends, this vacation home is the perfect retreat. Experience the magic of this beautiful area for yourself!

Superhost

Home in Readsboro

4.86 out of 5 average rating, 125 reviews

December in Peaceful Vermont (Pet Friendly)

Country Home, nestled in the Green mountains, panoramic views, with access to the road. A babbling brook to lull you asleep from the master bedroom, a clawfoot soaking tub, stocked house. Hiking, antiques, shops, lakes, ski, snowboard, covered bridges, local inns, mountain views! Enjoy Vermont! Scenic roads, nearby Mt. Snow, VAST snowmobile trails, Mt.Greylock, Mass MOCA museum, N.Adams, MA, Berkshires. Bennington Wilmington. PEACEFUL & PERFECT Vermont getaway! ☺

Guest favourite

Flat in Williamstown

5 out of 5 average rating, 116 reviews

Downtown | Waterfront | Walk to Shops

★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upgraded with the discerning guest's convenience in mind. The property is in the midst of Williamstown's popular spots: Williams College campus, theaters, museums, restaurants, shops, and golf course. It also sits by the rushing, sometimes tranquil, Green River where you can sit back, relax and enjoy the fire pit.

Superhost

Flat in Brownsville

5 out of 5 average rating, 3 reviews

Mountain Getaway

Nestled beside a hemlock grove and abutting a mountain meadow, this spacious, sun-filled rental is for the main floor of an end-unit condo, which sleeps up to two. Step out the door and hit the trails on foot or bike. You will find waterfalls, meadows, and more without leaving the property. Within a 30 minute drive you will find all the gems of a VT getaway. Maple farms, breweries, skiing, farmers markets, antiques etc!

Guest favourite

Home in Cavendish

4.95 out of 5 average rating, 22 reviews

Charming New England Cape- 10 Minutes from Okemo!

Relax with the whole family, or friends at this peaceful place to stay. Close to many local ski resorts, hiking trails, trophy fishing in the Black River off Route 131! Close to Ludlow And Historic Windsor and Woodstock VT! Only a 10 minute drive to Okemo Mountain and Jackson Gore! 30 Minutes to Killington Mountain and Magic Mountain 40 Minutes to Bromley Mountain Accessible to the natural beauty of Vermont!

Superhost

Townhouse in Peru

4.68 out of 5 average rating, 19 reviews

The Best Vermont Has to Offer!

GET AWAY to where you will have the best of all worlds! Within minutes of our beautiful spacious townhouse, there’s skiing, hiking, biking, horseback riding, Bromley Mountain Adventure Park with their famous Alpine Slide, golf, fly fishing, and every other outdoor activity you can think of. Yet nearby, there are also high-end designer outlets, local craft stores, spas and phenomenal restaurants.