Holiday rentals with outdoor seating in Windham

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Windham

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite

Tent in Middletown Springs

5 out of 5 average rating, 43 reviews

Green Mountain Nugget Private tent site for two!

Closed Sept 15-July 1. New 9-18 holes DiscGolf onsite! Enjoy a get-a-way for two in a private, spacious tent, listen to the river as you relax out of doors on a queen size bed. Set in our meadow between a pond and river and engage with nature. Spend the evening under the stars and around the campfire (wood included), relax at the private beach, or visit the nearby lakes, state parks, stores, restaurants or Slate Valley Trails. Convenient drive to the tent. Bring towels, water shoes, & charcoal.

Guest favourite

Guest suite in Shaftsbury

4.99 out of 5 average rating, 158 reviews

Peaceful Get Away at Birds of a Feather Farm

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. Spa services are available. For Booking & Fees contact host.

Guest favourite

Cabin in Stoddard

4.97 out of 5 average rating, 154 reviews

Secluded Renovated Retreat Surrounded by Nature

Get away from it all in a secluded, yet modern cabin, which guests have loved for its "silence and beauty" and called "peaceful" and "serene". Located on the Lakefalls Estate, which maintains the roads, Mended Oar features heated floors throughout, a well-furnished kitchen with quality appliances and equipment, and luxurious linens. Hike the many trails outside the door on the snowshoes you'll find, then come inside to enjoy the wood burning fireplace (wood provided) and play a board game.

Guest favourite

Yurt in Cambridge

5 out of 5 average rating, 9 reviews

Glamping Tent w/heater

All you need for a memorable glamping experience. The amazing views and comfortable accommodations, a roaring bonfire and candlelight, miles of trails and peaceful surroundings. Canoeing, fishing, hiking, exploring, antiquing, apple picking, leaf peeping - it's all close by and the choices are all yours. You can also just sit in the sun, admire the views, watch the hawks circle above and soak in the peace and quiet. Propane heater included. This should not be used all night or while sleeping.

Guest favourite

Home in Petersburg

5 out of 5 average rating, 105 reviews

Private Mountain Lodge-Amazing views, cozy vibes

Skiers and nature lovers! 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.

Guest favourite

Home in West Windsor

4.93 out of 5 average rating, 42 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

Home in Bridgewater

4.95 out of 5 average rating, 43 reviews

Killington Ski House Close to Skyeship, Woodstock

Escape to Vermont with central access to the mountain, dining, breweries, shopping, and more! The iconic Gondola House is a 3-level home comfortably sleeping up to 10 people with 5.5 bedrooms and 2 bathrooms. 10 min to Skyeship Lodge. 5 min to Long Trail Brewery. 15 min to Woodstock. 16 min to Bear Mountain lodge. The space includes a large open living, dining and stocked kitchen with dishwasher. Mud room with laundry. Gorgeous outdoor hot tub, covered porch with grill and plenty of seating.

Guest favourite

Chalet in Dover

4.95 out of 5 average rating, 120 reviews

Hot Tub-8Min Mt Snow Ski-Game Room-FirePit-Dogs Ok

✔ 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 in Granville

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

Cottage in Monroe

4.91 out of 5 average rating, 119 reviews

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

Guest favourite

Apartment in Williamstown

5 out of 5 average rating, 119 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.

Guest favourite

Cabin in Fort Edward

4.95 out of 5 average rating, 307 reviews

Farm Stay! - 20 min from Lake George-30 Saratoga

• A 10-acre farm with a cozy 10x16 cabin, queen-sized bed. • Proximity to Lake George, West Mountain, Gore Mountain, and Saratoga Springs • Amenities, including WIFI, TV, fire pit, BBQ grill, fridge, microwave, coffee maker, heat, and AC. • The camp has an outdoor handwashing station with running water provided by a hose, an indoor heated shower, and a port-a-potty for bathroom needs.