Holiday rentals with outdoor seating in Winhall

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Winhall

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Guest favourite

Home

5 out of 5 average rating, 103 reviews

Private Mountain Lodge-Amazing views, cozy vibes

Book your holiday get away! An incredible "wrapped in nature" experience in your own private lodge! Just 3 hours from NYC and Boston, perfect for those looking for privacy, views and luxury conveniences and events. Outdoor hot tub, sauna, game room/bar area, kitchen, large yard, fire pit, Peloton bike, local lake access and skiing! Something for everyone! All season fun-hiking, concerts, shopping, skiing, fishing, and world class art. Near Williamstown, MA, Southern VT, and so much more.

Superhost

Cabin

4.9 out of 5 average rating, 278 reviews

Mountain Cottage Spectacular Views

This lovely cottage sits on 90 acres featuring gardens, fruit groves, forest, and the Hoosic River. Spectacular views of Mt Greylock. Truly an idyllic location, the perfect retreat for a lover of the outdoors but also close to cultural offerings. Less than 10 minutes to downtown North Adams and Mass MOCA. Williamstown and the Clark Art Institute are nearby as well. Plenty of long or short hikes, scenic walks and bike rides as well as local restaurants and shops that are easily accessible.

Guest favourite

Home

4.97 out of 5 average rating, 157 reviews

Bernie's & Betty's

Comfortably sleeping 6 with a large yard, screened in porch, and newly renovated bathroom, this charming 3-bedroom house is perfect for families looking for fun and adventure in the beautiful Berkshires. Minutes from Mass MoCA, Williamstown (including the Clark Art Institute), and the Appalachian Trail, it is also an easy trip to Lenox (including Tanglewood) and other South Berkshire attractions. If you like the outdoors, you will love the easy access to ski slopes, hiking and biking trails.

Superhost

Tiny home

4.78 out of 5 average rating, 92 reviews

Tiny Home w/ Parking - Pet Friendly & Fireplace!

Beautiful Bellows Falls Tiny Home named Sky’s the Limit! Anything is possible here. Please join us in the first ever unveiling of Airbnb for this quaint tiny home! It is near a plethora of shops and restaurants in the historic town of Bellows Falls. Explore for yourself, or bask in the heat of the fireplace inside the house and fire pit outside. For hikers and skiers, this home is a hidden gem. Okemo is just 37 minutes driving, and there are scenic running paths and hiking spots within town!

Guest favourite

Cottage

4.9 out of 5 average rating, 156 reviews

Green Mountain Country Cottage

Four bedroom cottage centrally located within less than 35 min. of 4 ski resorts, and next to the former Tater Hill golf club. Access to snowmobile trail on site, X-country skiing, hiking, fishing, shopping, restaurants, state parks nearby. In summer and fall mushroom foraging is very productive. For history buffs there is a revolutionary war era cemetery next to the property. Sleeps 10 to 12. The cottage is only available to family groups or responsible adults over 25. NO PARTYING ALLOWED.

Guest favourite

Home

4.93 out of 5 average rating, 40 reviews

Chuck's Place

Chuck's is a neat and tidy stand alone home dedicated to vacation rentals. Fully stocked! Private and convenient on 7 sunny acres overlooking Mt Ascutney. Plenty to do out your door- hiking, snow-shoeing, skating, sledding, skinning and family-friendly skiing over at Ascutney. Brownville Butcher and Pantry is an active gathering place in the village. The best meats and fish anywhere! More downhill and cross-country/skate skiing, restaurants, pubs, and breweries all within 25 minute drive.

Guest favourite

Treehouse

4.98 out of 5 average rating, 225 reviews

Glamping Cabin with Hot Tub on Flower Farm

<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday and immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened 'walls' to let in the breeze (& keep out the bugs), the handmade tiny cabin invites you to pause and reconnect. An excellent base camp from which to explore southern Vermont, or simply stay put and recharge.

Guest favourite

Cottage

4.96 out of 5 average rating, 213 reviews

Vermont Treehouse - Romantic Private Elegant

3 night minimum, unless prior approval, self checkin. Work remotely. This romantic, elegant, private getaway for two (or one) in our "Treehouse" with sleeping loft, full kitchen & bathroom, screened porch, deck, sauna, WiFi, BBQ grill, etc. Overlooking pasture & mountains. Enjoy the property with 3 miles hiking/snowshoe trails. Guest house on 160 acre private horse farm. Lots to do at nearby ski areas, shopping, hiking, biking, theater in summer. Or just relax. Discount for longer stays.

Guest favourite

Chalet

4.95 out of 5 average rating, 112 reviews

8Min Mt Snow, Ski, DogsOk, HotTub, FirePit, GameRm

✔ 8 Minutes to Mount Snow, 30min To Stratton, 60min to Okemo ✔ 4 Bedrooms, 3 Bathrooms, Sleeps 10 comfortably ✔ Hot Tub Under Pergola & String Lights ✔ String-Lit Fire Pit Area w/ Adirondack Charis ✔ Game Room With Air Hockey & Ring Toss ✔ Dog-Friendly ✔ Lake Whitingham/Harriman Reservoir is 20 minutes away to enjoy boating & fishing ✔ Fast Wifi For Remote Working & Streaming ✔ Quiet, Peaceful, & Private ✔ High Chair, Pack N' Play Provided ✔ All Linens/Towels/Soaps Provided

Superhost

Campsite

5 out of 5 average rating, 3 reviews

Slateville Farm ~The Pines ~ Secluded Campsite

The Pines is our last addition to Slateville Farm campsite family, it sits high on a nob among old growth pine trees & is our most remote secluded site. Trail connected, a 4x4 vehicle is needed to access the site. Seasonal sunset views are enjoyed through the trees and the site can comfortable accommodate 2-3 tents. We offer 4 wooden Viking Chairs which sit around the stone fire pit, equipped with a swivel park grill, a wooden picnic table & of course its very own custom built outhouse.

Guest favourite

Home

4.98 out of 5 average rating, 186 reviews

Magical Farm Getaway - a must visit!

Beautifully restored 18th century farmhouse situated on 4.6 private acres within a 180 acre working farm. Five bedrooms, wood stoves, ample living space, and a cheery sun room with gorgeous views make this house one of a kind. Our backyard features an in-ground, heated, salt water swimming pool (open May to mid-Oct), fire pit (open year-round), large outdoor dining table, gas grill, and a deck with lounge seating and jacuzzi (open year-round). Parties and events are not allowed.

Guest favourite

Guest suite

4.99 out of 5 average rating, 155 reviews

Peaceful Stay at Birds of a Feather Farm & Spa

Our cozy upstairs studio can accommodates up to 4 and is separate from the main house. Plush towels, linen, pillows and blankets. Kitchenette is fully stocked with everything you need for cooking. The private entrance is equipped with punch key lock to facilitate easy self check-in. A queen size sleep number bed, queen size pullout couch, table with four chairs, a dresser, one bathroom with shower, smart TV and WIFI. Heat and cooling. A spa is available and infrared sauna.