
Tiny house vacation rentals in Windham County
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Top-rated tiny house rentals in Windham County
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Family-friendly tiny house rentals

Cozy private cottage in the woods of Vermont
Ice Pond camp was exactly as Darva described it. Quaint, cozy, very well kept clean, and comfortable. Darva was quick to connect with many details nearly as soon as I booked, and provided the necessary communications throughout my stay. I love the history of the property and how it has such meaning. Darva and her family have a wonderful place with all the needed amenities. Thanks so much, Darva, for sharing this special place with the rest of us.

Beautiful Art Studio with hot tub/sauna #1 Airbnb
The cabin was beautiful and perfect for a getaway from the city! We loved watching the sunset from the hot tub and cooking in the beautiful kitchen.

Last Frontier Log Cabin
We had a wonderful stay here for our weekend ski trip! The place was beautiful and had everything we needed and the area was so peaceful. Just make sure to prepare to lose service in the area, but once you get there the WiFi is great! The hosts were very communicative and proactive about a snow storm that hit during our stay as well. We would love to visit again!

Fernando’s nature hideaway - XCountry Skiing
Nice place to stay. Beautiful area.

Cozy Mountain Getaway
Really enjoyed our stay. Close to skiing. Ashley was a wonderful hostess.
Tiny house rentals with a patio

"Mountain View" Rustic Cabin Retreat w/Fireplace
This place had so much more to offer than we were expecting. The cabin was clean, well-equipped yet minimalistic, and very cozy. You can tell that great attention was put into the details, from the rustic decor, to the flannel robes, to the french press coffee maker. Everything was beautiful and functional. The property has so much to explore- wish we had more time to explore the grounds and soak it all in before we had to leave. Sean was also an awesome host, he was walking around the property when we arrived and helped direct us to our cabin. He was super responsive when the wood stove needed more pellets, and offered us some recommendations for dinner! All of the other staff and guests we encountered were lovely as well. This place is perfect for anyone looking to unplug and connect with nature while still having access to toilets, running water, etc.

“Hickory” Rustic Cabin Retreat with Fireplace
Beautiful glamping experience! Highly recommend if you're looking for a cozy haven in the heart of nature, rustic, woodsy, and peaceful. The cabin was adorable and well-furnished, the bed was much more comfortable than it looks in the picture and came with both a soft quilt and a fur overlay, as well as fluffy pillows. The fireplace was a nice addition, and gas powered so it's easy to use. The hot tub was wonderful (although it is shared with other guests on the campground), there was a spot right next to the house for a great bonfire, and plenty to explore in the area. The port-a-potty next door was clean and not too bad to use. Host was responsive, very helpful and super nice! (he let us hang out on the grounds past checkout time, which was so appreciated.) The only thing I would reccomend is that if you're planning to build a campfire in a relatively rainy season (we came late May), pre-buy your own dry firewood as most of the wood here for sale was wet. Would come again!

Rooted Moon Retreat…Sun filled cabin in the forest
Fantastic little place! Cute and full of character. Loved the place while it’s not very large - we all felt like we had enough room. We wish we could have stayed another night. We look forward to a future visit to this quaint home!

“Sugar Maple” Rustic Cabin Getaway with Fireplace
Such a cozy and lovely stay! I slept so well in the comfy, warm bed, and waking up to the peaceful sounds of the woodland birds. I had a brief stay and unfortunately had to arrive late at night, but I was warmly greeted by so many sweet kitties! Thank you Sean and others at the camp for making me feel welcomed and helping to for create such a peaceful place to stay. It was so fun to explore the grounds!

A frame cabin with Hot tub near Stratton, VT
my 2 best friends stayed the weekend for my 30th and it was amazing, a dream home, so very peaceful. all of us are moms, and this place was so relaxing and we will definitely be back. Christina even left a bottle of bubbles which was just what we needed. she is an amazing host

Riverside Wellness Escape: Cold Plunge & Sauna!
Wonderful stay, coming from west Springfield to the beautiful nature that this tiny home had to offer was so worth it! Loved every part of it the beautiful river and the amazing sauna was incredible! The owners were so welcoming and caring! So worth it ❤️

The Pines Cabin | New Tiny Home Near Mt Snow!
Lovely home. Small but just right for the two of us. Clean, nicely furnished. Full amenities like a full-size house. There’s no TV but we didn’t miss it (there is wifi for your devices). Kitchen has just about everything needed (a nonstick/ceramic/carbon steel pan would have been helpful for eggs). Ductless mini-split for heat/AC. Wish we could have used the fireplace, but there was too much snow to find kindling. Stairs/ladder up to the loft are not for the clumsy nor faint of heart, but we didn’t have any issues. Bed in the loft was comfortable. Bunk beds on the main floor that we didn’t use. Overall, a very nice place. We would have no hesitation to stay here again.

Bambi Inn Jamaica
Airsteam was beautiful and clean. Jonathan always responded within a few minutes. Eating places were usually a 25+ minute drive. A nice stream was nearby. The questions I did have were very quickly answered. Wouldve been nice if Mother Nature welcomed us with good weather rather than saying goodbye with nice, sunny, dry weather. Good Breakfast suggestions: Cup & Saucer; Wilmington Bobs Diner; Manchester
Tiny house rentals with outdoor seating

Serenity Now - Couples Retreat or Writer's Dream
great place to stay, peaceful, quite, and restful. Lisa was responsive and gave us our space to have fun. we will definitely look forward to going back again.

Stratton; 5 min. Pikes Falls, 1 min. Fire pit
What a perfect tiny home and what a perfect stay! Very quiet rural location, the tiny home is pristine and cozy, decorated with love. Very good heating system, good water pressure in the shower. Would definitely stay again.

Jamaica Mod A Frame
Awesome place near Stratton and Mt snow. Beautiful surroundings and tranquil stream nearby. Wood burning hot tub worked really well. I started it and went to dinner for a couple hours and when I got back it was over 100 degrees.

Vermont Treehouse - Romantic Private Elegant
Warm, inviting cabin with gorgeous 360 degree views, giving the feeling of living with nature rather than apart from it. It is obvious that a great deal of care and love went into this place... many small, artistic details that create a magical vibe. We were cozy and comfortable during a snowstorm and quite content to stay home and soak up the peace and beauty. Kitchen was great for meal prep and the coffee and breakfast cake were appreciated after our long journey. The sauna was delightful, restorative and well equipped; we enjoyed it tremendously! Next time we would pack robes for walking back upstairs after sauna-time (we didn't realize that the sauna area was accessed from the outdoors rather than inside the cabin). We had plenty of privacy for our winter retreat, which we value. We didn't want to leave this special place, and are already plotting our return. Many thanks Sandy and Jim!

A-Frame Mountain Retreat near Manchester
The place is beautiful, private, quiet, cozy. Monique is super accessible and friendly, I felt super comfortable being able to take my dogs. The house is complete in the details, they thought of everything to make the place as pleasant as possible! Thank you Monique...

Cheerful cabin retreat in the woods and mountains
What an incredible place. Quiet, beautiful, restorative. The cabin's amenities make it easy to enjoy your time inside and outside the cabin. The bed and pillows are well-maintained and comfortable, and the sheets are of high quality. The light pollution is much lower here, so star gazing is an incredible experience. There are hiking/snowmobiling trails accessible by a short walk from the house. If it is tick season, be prepared with repellent!

Vermont Cabin
Chads cabin was a perfect fit for our short stay. Great for a weekend getaway. This little Aframe was exactly as described and met our needs.

Cozy Lakeside Tiny Home, Near Skiing
Thoroughly enjoyed staying at Christopher's Tiny House. it was just right for my minu retreat. The space was just as described and very calm and welcoming.
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- The Shattuck Golf Club
- Dorset Field Club
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area
- Hildene, The Lincoln Family Home
- Clarksburg State Park
- Ekwanok Country Club
- Brattleboro Ski Hill
- Bretwood Golf Course
- Hooper Golf Course
- Fox Run Golf Club