Tiny house vacation rentals in Windham County

Find and book unique tiny house rentals on Airbnb

Top-rated tiny house rentals in Windham County

Guests agree: these tiny house rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

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!

Guest favorite

Tiny home in Putney

4.94 out of 5 average rating, 112 reviews

Cottage core dreamland A woodland retreat

Take it easy in this unique and tranquil getaway. A woodland retreat in a sound sanctuary where you have the opportunity to receive a sound healing session, or simply rest in quietude. Specialized ceremonies are offered as well please inquire further. It is a peaceful cabin, on the same property as the owners, with dogs and free range chickens. There is a back deck, space for a fire, a full kitchen and bathroom. There is a loft for sleeping so you must be comfortable going up and down a ladder

Superhost

Chalet in Wilmington

4.79 out of 5 average rating, 188 reviews

Vermont Cabin

Looking for a quick getaway to take in the culture of southern Vermont? Check out this cozy rustic cabin in the woods that comfortably sleeps 2 and is centrally located between skiing, hiking, golfing, camping and unique dining and shops. The cabin is 5 miles from Mount Snow and 5 miles from historic downtown Wilmington, nestled on a quiet private road, but also located just a short walk from the free Moover public transportation Route 7 East Dover Road Stop. Free parking for three vehicles.

Superhost

Home in South Londonderry

4.85 out of 5 average rating, 149 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

This NEW and VERY romantic abode…The Honey Pond Treehouse is made especially for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…You will enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes! @bentapplefarm

Guest favorite

Tiny home in Whitingham

4.91 out of 5 average rating, 98 reviews

Cozy Lakeside Tiny Home, Near Skiing

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store, located 5 minutes away, will make you fresh egg sandwiches, pastries, and coffee. For lunch, come in and get fresh made subs or our famous brick oven pizza slices. A perfect getaway for couples, friends, or family in every season. Enjoy kayaking, fishing, ice skating and boating on serene Sadawga Lake. It's a quick drive to skiing at Mount Snow, shopping and dining in Wilmington, and direct access to the VAST trail.

Top guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 265 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite

Cottage in Londonderry

4.96 out of 5 average rating, 217 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 favorite

Tiny home in Athens

4.95 out of 5 average rating, 201 reviews

Luxury “Tiny” House, Immersed In Nature (Timbery)

The Timbery: This is a brand new, fully handmade, timber frame "tiny" house. The house is nestled in the forest, accessible by foot. With 17 vertical ft. of floor to ceiling windows, this property represents a unique experience to fully immerse yourself into nature. It is like lying down on the forest floor and looking out the front of your tent. Except instead of wet sleeping bags and dirty hair, you enjoy a queen sized bed, in home theater, full kitchen and 71in soaking tub. NO SMOKING

Guest favorite

Tiny home in Brattleboro

4.86 out of 5 average rating, 148 reviews

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

Guest favorite

Tiny home in Jamaica

4.94 out of 5 average rating, 1,254 reviews

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

Top guest favorite

Barn in Marlboro Township

4.96 out of 5 average rating, 312 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Top guest favorite

Cabin in Guilford

4.96 out of 5 average rating, 530 reviews

Serenity Now - Couples Retreat or Writer's Dream

COUPLES RETREAT or SOLO EXCURSION Perfect setting to swoon your partner or write the novel of your dreams. A romantic destination for Engagements, Honeymoons & Anniversaries. Guilford Vermont - no cleaning fee - Easy drive from Boston & NYC ROMANCE SPECIAL - Guests staying 4-nights or more, receive Vermont Made hard cider, cheese crackers and chocolate ($50.00 value) Ask me about ELOPEMENT & VOW RENEWAL CEREMONIES

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What guests are saying

“Elm” Cozy Pond-side Cabin w/wood stove

4.92 out of 5 average rating, 115 reviews1 month ago

super cute quiet accomodations and perfect spot for a quick birthday getaway. Sean was super friendly, very responsive, but also gave privacy and space. the only thing I recommend is bringing a roll of TP with you as there wasnt any in the outhouse, but we had some because we always bring w/us just in case and I'm very confident Sean would have gotten us some right away if we asked. We would definitely go back.

Tiny home in Brattleboro

What guests are saying

Rustic Cabin in foothills of Green Mountains

4.99 out of 5 average rating, 181 reviews1 month ago

The only airbnb we have ever returned to. Sean and Nicole are the best hosts and very cool people. The cabin is a perfect little off grid home nestled away in the woods. Extremely clean and cozy. Great little stove kept us very warm during the cold windy winter nights. Very comfortable bed. Quick 10minute drive to restaurants and activities. Don’t hesitate to stay here! Thanks for another fantastic weekend.

Tiny home in Dover

What guests are saying

Foxglove Tiny House - a modern tiny getaway

4.77 out of 5 average rating, 129 reviews1 month ago

The tiny home was truly GORGEOUS! Very clean and had a lot of amenities. It was perfect for a quick getaway with my fiancé as we looked at wedding venues in the area. My only grievance was the lack of service in the area and everything was closed early but that’s just the area itself - though was saved with the WiFi hotspot available! If you’re looking for a quiet private getaway to unplug, this is definitely a great choice. The aesthetic was awesome. They included a very helpful binder that was very thorough with everything that made the entire place foolproof. The fireplace was a favorite. Full kitchen. The hosts were also very responsive in allowing us to have a late checkout before our long journey home. One of my favorite tiny homes I’ve rented through Airbnb.

Tiny home in Jamaica

What guests are saying

Chapel of Love - Tiny House Life

5 out of 5 average rating, 4 reviews1 month ago

The Chapel of Love housed me for over three months. It met or exceeded all of my expectations. Small, yes. Efficient, very. Lots of windows for sunlight from all angles. Everything I needed in a nice, homey interior. Plenty of storage for food and sundries. Great additional storage in the two loft spaces, which made the long-term stay perfectly doable, even with a bunch of ski equipment/gear. Domenic and Sarah are excellent hosts: on-property; extremely responsive; there to assist (quickly) with any concerns or issues. Really friendly folks!

Tiny home in Jamaica

What guests are saying

Stylish Mountain Home Near Ski, Golf + Manchester!

4.71 out of 5 average rating, 41 reviews2 months ago

A few of us stayed here for a weekend ski trip in Stratford. Perfect location. 15min from Stratford and 10min from Bromley. Tons for restaurants close by and cute dowtown district for shopping. House was perfect. A lot bigger than the pics show. 4 bedrooms with mutiple beds. Good for adults and if u have children. Hot tub nice bonus for sore muscles after skiing. Would definitely book here again.

Home in Winhall

What guests are saying

Riverbed Treehouse @hot tub & a new sauna & views!

4.86 out of 5 average rating, 116 reviews4 weeks ago

Ben is probably one of the host with the most beautiful choice of places to pick! I can’t wait to come back and try them all! Our stat in LondonDerry was amazing it was the best surprise for my girlfriend’s birthday, if you’re looking for a romantic and relaxed vacation in a quiet and beautiful place you can’t choose a better one! Definitely will come back again, Thank you Ben for the amazing experience you let us have.

Treehouse in Londonderry

What guests are saying

Tiny A-Frame Rest House in Woods

5 out of 5 average rating, 22 reviews5 months ago

Absolutely a wonderful little spot. An amazing tiny home experience. My wife and I stayed for a few days to relax and unwind and it was just what we needed. The house was comfortable and beautiful, we enjoyed the view from the loft and also sitting on the deck. It was easy to find and Katie was very responsive and friendly.

Tiny home in Chester

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