
Tiny house holiday rentals in Windham County
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Top-rated tiny house rentals in Windham County
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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
We had a wonderful time in this beautiful rural Vermont oasis. Exactly what we were looking for! The place is quintessential VT…. So if you are looking to spend a few nights in a reconverted barn on farmland…. Well, this is it. We loved being able to walk the property, and the jacuzzi and sauna were a real highlight. Directions getting in and figuring out our building were a bit confusing at first but we figured it out. We had a few small issues but Ben was responsive and did his best to take care of them quickly - with varying levels of success. The outdoor area could use some easier access and a bit more attention, but we were told that it is in the works. We would stay again in a heartbeat!

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
Cabin was perfect for my partner and I. I’d recommend checking in with Ben whether your car is okay as mine is a FWD sedan and I had no issues this spring. The hot tub and fire pit was great. Unfortunately I didn’t get a chance to try the sauna but I had a look and it seemed awesome. Highly recommend New American Grill down the road. Will definitely come back one day.

Honeycrisp Cottage - A Tiny Timber Frame
Andrea’s place was stunning. Even though we had to head home early due to circumstances beyond our control with a Nor’easter that took place, Andrea was very understanding and accommodating. The accommodation was stunning. Modern, clean, and the views were immaculate. I can’t thank Andrea enough for being so easy to work with and being flexible with our check in and communicating! Thanks again, would highly recommend anyone looking!

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
We really enjoyed our stay and the town of Brattleboro as a whole. We loved the local restaurants and cafes. Kiplings and The Porch are a must visit. We found the recommendations in the welcome binder. While there we explored the trails surrounding the property. We did the full loop (yellow trail). It was about a mile and a half and a moderate hike, coming from a beginner. The interactions we had with Sean and others on the property were all pleasant. The cats roaming around the outdoor areas were adorable and fun to watch. We also really enjoyed the hot tub! The view is spectacular. Overall the stay was fantastic, just be aware this is an off grid kind of experience. This cabin is also down at the bottom of a fairly steep hill, making it more secluded but quite far from the wash house and hot tub. The cabin is a bit dusty and gets quite warm during the day. The bed and sofa are a bit uncomfortable but did the trick for a two night stay.

A frame cabin with Hot tub near Stratton, VT
Had a lovely couples weekend getaway at this airbnb! The place was very cute and cozy with a nice large kitchen - we enjoyed making meals together and there was plenty of space for all of us. It really nice to have a separate bathroom for each couple and the bedrooms were comfy with a really nice bathtub setup upstairs! The location was great - we did some hiking nearby and it was very quick to drive into the town and get groceries. Overall, had a great stay and would highly recommend staying here!

Riverside Wellness Escape: Cold Plunge & Sauna!
If you have found this gem consider yourself lucky. This peaceful escape is amazing. We loved listening to the sound of the river as we went to sleep. Waking up surrounded by the trees with the sun peaking through was incredible and we spent time on the riverside beach. We did a cold plunge and used the sauna - an incredible experience. A great way to slow down and enjoy life again. The Fat Crow restaurant down the street was top notch. Jocelyn and Ajay are awesome hosts. Already planning our next trip back.

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
My husband and I spent our honeymoon here for a week and it was absolutely amazing. Very beautiful area and it was the perfect amount of private. Lisa was amazing and responded quickly whenever we messaged her. The cabin itself was the perfect size and perfectly clean. 10/10 would recommend<3

Sage House at Camp Greenwood Vermont with Sauna
We went up to the area for 2-day wedding and this was such a great option for relaxation and restoration in between events. Thanks so much for a wonderful weekend!

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
Amazing, beautiful, comfortable, designed with every detail thoughtfully curated. Welcoming, incredibly spacious, calming… all while listening to the rushing waters of the river. You will not be disappointed. In fact, your expectations may well be exceeded. Thank you 🙏🏽.

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.
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Bousquet Mountain Ski Area
- National Museum of Racing and Hall of Fame
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Ekwanok Country Club
- Hooper Golf Course