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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.

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Cabin in Londonderry

4.94 out of 5 average rating, 343 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Cabin in Wardsboro

4.87 out of 5 average rating, 105 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Home in Winhall

4.95 out of 5 average rating, 125 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

Home in Winhall

4.88 out of 5 average rating, 162 reviews

The Mushroom House of Manchester Vermont

Welcome to The Mushroom House. Located at the end of a private road, the house is less than 4 miles from Manchester's outlet shopping, gorgeous hiking and unmatched dining. Our property features an open floor plan main floor with a kitchen, dining and living area that neighbors the master bedroom and bath. The back deck is a accented with string lights, a grill and comfortable outdoor furniture. Down stairs has two guest rooms with queens beds, a full bathroom and a den with full futon and tv.

Cabin in Londonderry

4.94 out of 5 average rating, 113 reviews

Green Mountain base camp for year-round adventure!

Featured on Levi Kelly's Cabin Tours & Lincoln Car Ad! Deerwood Hill is a 3.6 acre base camp for all Green Mountain adventures. Perfect retreat for all seasons! Within minutes to Stratton, Magic, Bromley, Mt Snow, & Okemo ski resorts! 1 hour to Killington! Under 30 minutes to wonderful Manchester! Let us take care of you in beautiful South Londonderry! ♥Comfortably sleeps 6 ♥2nd Bedroom is open loft with full bath ☒ Booking Guest must be 25. ☒ NO PARTIES, NO SMOKING, NO PETS @deerwoodhill

Home in Winhall

4.96 out of 5 average rating, 200 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Just minutes to skiing at Stratton Mountain, Bromley and Magic. Explore 27+ acres of forest with trails, river, sculpture gardens and private pond. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. A short drive to Manchester with shops and restaurants. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Chalet in Londonderry

4.93 out of 5 average rating, 102 reviews

10 min from Stratton! Log Cabin w/ Beautiful Views

Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

Cabin in Winhall

4.91 out of 5 average rating, 140 reviews

Snow Valley Cabin-Cozy Escape Near Skiing & Nature

The Snow Valley Cabin is a three bed one-and-a-half bath chalet-style house designed for your perfect Vermont getaway. Wooden vaulted ceilings, wood-burning fireplace, beautiful view of the snow-capped Bromley mountain, and Scandinavian style details. We are conveniently located on the edge of the Green Mountain Forest just 4 miles from Bromley, 9 miles from Stratton, 14 miles from Magic, and 12 minutes to Manchester. Stay here to relax and wind down with friends and family, and even pets!

Cabin in Jamaica

5 out of 5 average rating, 217 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Rental unit in Manchester

5 out of 5 average rating, 216 reviews

Private two-bedroom suite within a two-story house

This is a private suite located on the second floor of a house. Separate entrance. The owners live downstairs. Great location with mountain views. Please note: 1) Our kitchen is fully equipped, but it has a hot plate instead of the traditional stove. 2) Instead of a full-size living room there is a small sitting area with a TV in the same area where the kitchen is located. 3) Guests don't have access to the backyard/patio, but you can enjoy the outside seating set in front of the house.

Barn in Chester

4.99 out of 5 average rating, 580 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Cabin in Winhall

4.9 out of 5 average rating, 166 reviews

Contemporary 4 bdrm Cabin Hot Tub and Sauna

Our cabin is the ideal Vermont vacation spot, with soaring wood panel rooms, massive brick fireplace in the living room, large wrap around deck, hot tub and sauna. Room for all with four bedrooms, open concept living, dining room, living room, kitchen and lower level family room. The perfect Vermont get away. The cabin is located just minutes from Stratton mountain. We have weekend Shuttle service in our neighborhood to and from the mountain during ski season.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Winhall vacation rentals

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

Barn in Manchester

5 out of 5 average rating, 24 reviews

Bromley Barn

Rental unit in Winhall

5 out of 5 average rating, 9 reviews

Cozy Mountain Studio Retreat

Townhouse in Winhall

5 out of 5 average rating, 21 reviews

New! Vermont Getaway! Stratton - close to skiing!

Rental unit in Manchester

4.92 out of 5 average rating, 25 reviews

Manchester Cottage

Chalet in Winhall

4.92 out of 5 average rating, 39 reviews

Le Chalet : beautiful renovated home - Stratton

Chalet in Winhall

4.88 out of 5 average rating, 68 reviews

Spacious Chalet W/ Endless Entertainment THE BARN

Chalet in Winhall

4.97 out of 5 average rating, 90 reviews

Minutes to Stratton! Large, private home w. sauna

Chalet in Winhall

5 out of 5 average rating, 37 reviews

5 mi to Stratton! Cozy Chalet with Game Room&Deck!

Quick stats about vacation rentals in Winhall

Total rentals
300 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
7.4K reviews
Family-friendly rentals
260 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 vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 vacation homes 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 apartment rentals in Winhall?
Experience the best of Winhall with our apartment rentals, starting at about $110 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 chalet rentals in Winhall have air conditioning?
Absolutely! We offer over 20 chalet 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 apartment rentals in Winhall have free parking?
Absolutely! We offer over 10 apartment 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 Cabin Rentals in Winhall?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with free parking, over 10 homes with air conditioning, 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.

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