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Vacation rentals in Winhall

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Top-rated vacation rentals in Winhall

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Wilmington

5 out of 5 average rating, 8 reviews

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

Enjoy stunning lake & mountain views w/ easy access to hiking, swimming, boating, & fishing (kayaks, paddle board, and bikes included). Cathedral ceilings w/ beams provide a cozy feel & heated floors give an always-warm home in the winter. Covered deck w/ grill is great for outdoor dining. Additional features include outdoor hot tub, sauna, & quality game room (pool table, shuffleboard, foosball, ping pong). 4WD/AWD required in winter. Close to Mt. Snow & downtown Wilmington w/ shops and dining.

Guest favorite

Home in Cavendish

5 out of 5 average rating, 40 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

Apartment 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 favorite

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 favorite

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 favorite

Apartment in Wilmington

4.91 out of 5 average rating, 129 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

Guest favorite

Cottage in Fair Haven

4.92 out of 5 average rating, 151 reviews

Historic Cottage 2 Bedroom 2 Bath Fast Wifi

Ski season has begun! Picturesque cottage next to the Castleton River. You can wake up to the birds chirping and fall asleep to the frogs croaking. Hourly church bells ring throughout the day. Walk down the historic slate sidewalk to the park and local beer, pastries & the best diner! Minutes to many lakes, trails & mountain activities. Perfect for day trips to Killington, Okemo, Woodstock, Lake George, Vergennes, Rutland, Burlington & Saratoga Springs. Message us about seasonal discounts!

Guest favorite

Villa in Pownal

4.94 out of 5 average rating, 66 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!

Guest favorite

Condo in Stratton

5 out of 5 average rating, 12 reviews

Top Flr Duplex 3BR 4BA - Walk to All @ Stratton Mt

Rising Bear Duplex 411 at Stratton Mt-Seasonal Rental Available Spacious 3Br/4Bth Lodge on The Commons w/ Ice Skating Pond, Heated Pool, 2 Min Walk To Ski Family Friendly Spacious Lodge With Mountain Views, Excellent Location. Inspired by the great lodges, Rising Bear is located on the Commons, with ice skating, firepits and family activities. Convenient heated underground parking space and generous living spaces make Rising Bear ideal for bigger families and group gatherings.

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 favorite

Home in Wilmington

5 out of 5 average rating, 25 reviews

Kiki's Mountain Chateau

Refresh and reset within this spacious, serene space destined to be a memorable family retreat. A charming getaway with all the comforts of home with the best nature has to offer. Located in the small town of Wilmington and just a short scenic drive to Mount Snow. Local watersports, winter sports, nature trails, foliage, bird watching, stargazing and plenty of local charm. Kiki's has enough room for everyone to unwind or gather together. ***Hot Tub has arrived!

Guest favorite

Apartment in Williamstown

5 out of 5 average rating, 118 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.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winhall vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Stay near Winhall's top sights

Stratton Mountain Resort173 locals recommend
Bromley Mountain Ski Resort187 locals recommend
Johnny Seesaw's49 locals recommend
Mulligan's43 locals recommend
Red Fox42 locals recommend
Winhall Market38 locals recommend

Other great vacation rentals in Winhall

Guest favorite

Home in Wilmington

5 out of 5 average rating, 10 reviews

Countryside SKI Retreat - Indr Pool&HotTubGameRoom

Guest favorite

Condo in Dover

5 out of 5 average rating, 10 reviews

Cozy condo with direct mountain views and shuttle

Guest favorite

Townhouse in Winhall

4.96 out of 5 average rating, 23 reviews

New! Vermont Getaway! Stratton - close to skiing!

Guest favorite

Home in Monroe

4.92 out of 5 average rating, 13 reviews

The Camp

Superhost

Home in Manchester

4.85 out of 5 average rating, 34 reviews

Your VT Ski House: Fireplace, Indoor Pool, Dogs

Superhost

Townhouse in West Dover

4.74 out of 5 average rating, 19 reviews

Beautiful 4 Bedroom Townhome Minutes from Mt Snow

Guest favorite

Home in Dover

4.88 out of 5 average rating, 66 reviews

Large Mount Snow Ski House with Hot Tub

Guest favorite

Home in Wilmington

4.87 out of 5 average rating, 101 reviews

MtSnow * Hot Tub * Pool * Air Hockey * PingPong * Darts * 16ppl

Show all

Quick stats about vacation rentals in Winhall

  • Total rentals

    320 properties

  • Nightly prices starting at

    R2,054 ZAR before taxes and fees

  • Total number of reviews

    7.5K reviews

  • Family-friendly rentals

    270 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    50 properties have a pool

Frequently Asked Questions

  • Are there Winhall townhouse rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 townhouse rentals with pools in Winhall, available on Airbnb. Make a splash and soak up the sun in style!

  • Do condo rentals in Winhall have wifi?

    Absolutely! We offer over 30 condo rentals with wifi in Winhall. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Winhall?

    Experience the best of Winhall with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly vacation rentals in Winhall?

    Winhall has more than 260 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do cabin rentals in Winhall have air conditioning?

    Absolutely! We offer over 10 cabin rentals with air conditioning in Winhall. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Winhall?

    Yes! Work meets play with ease at over 150 vacation rentals in Winhall featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do chalet rentals in Winhall have free parking?

    Absolutely! We offer over 30 chalet rentals with free parking in Winhall. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Winhall have a kitchen?

    Absolutely! We offer over 20 cabin rentals with a kitchen in Winhall. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Townhouse Rentals in Winhall?

    Enhance your stay in our Townhouse Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with free parking, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there pet-friendly vacation rentals in Winhall?

    Four-legged friends are welcome in Winhall. Choose from more than 120 vacation rentals for guests traveling with pets.

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Winhall