Holiday houses in Winhall

4.94 out of 5 average rating, 348 reviews

Cabin in Londonderry

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!

4.95 out of 5 average rating, 141 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!

4.98 out of 5 average rating, 101 reviews

Chalet in Winhall

Mountain view chalet with hot tub & fire pit!

Welcome to the Vermont View Chalet! This spacious, family-friendly property is perfect for year-round enjoyment. With the mountain view as your backdrop, come unplug by the fire pit and unwind in the hot tub. Perfectly situated between Manchester (shopping & dining) and Bromley/Stratton (skiing and entertainment). You're also just 2 minutes away from the Appalachian trail for the best hiking and fall foliage Southern Vermont has to offer. Look no further, you've arrived at your destination.

4.96 out of 5 average rating, 251 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

5 out of 5 average rating, 245 reviews

Cabin in Jamaica

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.

4.99 out of 5 average rating, 257 reviews

Apartment in Manchester

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.

4.94 out of 5 average rating, 1,270 reviews

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

4.96 out of 5 average rating, 351 reviews

Cabin in Winhall

A-Frame Mountain Retreat near Manchester

The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 6 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

4.9 out of 5 average rating, 120 reviews

Tiny home in Athens

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

4.99 out of 5 average rating, 135 reviews

Home in Londonderry

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

4.95 out of 5 average rating, 148 reviews

Condo in Stratton

Cozy condo within walking distance to the slopes.

Cozy condo within walking distance of the slopes and restaurants and shops at Stratton Mountain Village. After a day on the slopes relax in the hot tub or take a dip in the heated pool or maybe enjoy some time in the sauna. Then enjoy sitting in front of the gas fireplace and maybe watch a movie. TV is a smart TV, basic cable is included - personal password needed for Netflix, Hulu, etc.

4.98 out of 5 average rating, 386 reviews

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.

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Popular amenities for Winhall holiday rentals

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Wi-Fi

Pool

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Air conditioning

Other great holiday rentals in Winhall

4.87 out of 5 average rating, 15 reviews

Relax & Recover Retreat | Hot Tub + Sauna + Gym

HollyRating, 5 stars1 month ago

Meredith's place was so comfortable, relaxing and very clean! We enjoyed our stay. The host's were very attentive and even reached out to us beforehand to make sure the bed situation was going to work for the number of adults that we had. We had 9 ladies staying for a ladies' weekend and we were comfortable. The location is private. Also it is near to a lot of hiking and walking options. Great place!

5 out of 5 average rating, 74 reviews

Cabin in Winhall

Log Cabin Escape Close to Skiing & Shops

LindaRating, 5 stars3 months ago

Pristine, cozy cabin in the heart of the forest, but yet close to everything. So many little extras that make you feel at home. Directions to everything in the home are clear and precise. Ian and Mikayla checked in throughout the trip and were available for any questions. The views are amazing. Our family enjoyed our visit and will definitely be back. Thank you for sharing your beautiful home!

5 out of 5 average rating, 14 reviews

Entire Chalet in Winhall, Vermont

BrianRating, 5 stars3 months ago

We enjoyed the stay, the accommodations were perfect for our family, four adults and two young children. The home is very well organized and comfortable, with things to do for the kids. Recommended.

5 out of 5 average rating, 11 reviews

Home in Peru

Highland Haus: stunning ski getaway with hot tub

AbigailRating, 5 stars3 weeks ago

The home and location are great, but the hosts are what make this place. They go above and beyond to make your stay special.

4.98 out of 5 average rating, 183 reviews

Cabin in Granville

Quaint log cabin nestled in the woods

RichardRating, 5 stars1 week ago

Desma's cabin was the perfect getaway for us... tucked away in the woodline with a small stream running through the property. Peaceful, wonderful. Comfortable. We highly recommend Desma as an excellent host and her lovely cabin as an excellent place to stay for a week to unwind.

Superhost

Chalet in Winhall

4.9 out of 5 average rating, 10 reviews

Clean cozy Stratton chalet

SherylRating, 5 stars9 months ago

Rachael's place was spacious and comfortable, with everything we needed. A great spot to unwind and enjoy all southern Vermont has to offer.

4.95 out of 5 average rating, 66 reviews

Cabin in Winhall

Stylish Getaway w/ Hot Tub & Firepit Near Stratton

Venkat SaiRating, 5 stars1 month ago

It was same like looked in pictures. Secluded nice place. Our family enjoyed the stay. Irina helped us with everything needed and we loved the stay. In winter we will come back again. Only thing for summer is NO air-conditioning but she has fans in every room.