Holiday rentals with outdoor seating in Windham

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Windham

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

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Guest favourite

Chalet

4.99 out of 5 average rating, 163 reviews

Family Ski Chalet 8 mins from Stratton 15 Mt Snow!

Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back and enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled June 2023! Open floor plan w/wood burning fireplace. Main bedroom has Qn bed & twin bunks. Finished basement with new Qn size bed and twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property!

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.

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

4.92 out of 5 average rating, 39 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

Chalet

4.9 out of 5 average rating, 194 reviews

A+ Stratton shuttle, Hot Tub, Sauna, 2 masters

GREAT WINTER 2 FAMILY SHARE 4 BD 3.5 BA with 2 MASTER SUITES THIS HOUSE IS NOW BEING MANAGED BY CHRIS YOU CAN BOOK THROUGH HIM USING THIS LINK: https://www.airbnb.com/rooms/1191997457007443812?guests=1&adults=1&s=67&unique_share_id=e02ff22b-7f12-4170-8aee-f9a9f1ced1ec HOT TUB, SAUNA, 2 FIREPLACES, BBQ GRILL, OUTDOOR FIRE PIT, HEATED BEDS AND FLOORS, PIMA COTTON LINENS, GOOSE DOWN DUVET, COTTON TOWELS, FIREWOOD PROVIDED. SMART HOME WITH HOME THEATER , XBOX, HULU, NETFLIX, AND PRIME.

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

Cabin

4.97 out of 5 average rating, 151 reviews

Stylish Waterside Retreat Surrounded by Nature

Mended Oar Outpost offers peace and solitude in a beautiful and secluded setting, part of the 250-acre Lakefalls Lodge estate. The view from the enclosed wraparound porch of Chandler Meadow and the adjoining 10,000 acres of conserved land is truly breathtaking. You can go swimming, hike for miles in the woods, or spend the day canoeing or kayaking from your private dock as you watch Chandler Meadow's otters, beavers and blue herons . You might even see a moose grazing at the water's edge.

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, 111 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.