Tiny house holiday rentals in Windham County

Find and book unique tiny home rentals on Airbnb

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Popular amenities for tiny home rentals in Windham County

Family-friendly tiny home rentals

Top guest favourite
Cottage in Dover
4.96 out of 5 average rating, 237 reviews

Cozy private cottage in the woods of Vermont

YehyeonRating, 5 stars6 months ago
Darva's camp is amazing. It was so cozy and private, yet it didn't feel too isolated or scary. Darva was really understanding and communicative. There's so much nature to explore around the camp, and you must sit outside at night and see the stars! We loved exploring the area too, food was good wherever we went & people there are super nice. We had the best time - our kid and doggo didn't want to leave. We will be back on a longer stay!
Superhost
Cabin in Londonderry
4.76 out of 5 average rating, 399 reviews

Beautiful Art Studio with hot tub/sauna #1 Airbnb

JoseRating, 5 stars1 week ago
Had a really great time. Ben was quick to respond and accommodating. His place we rented for 4 days was exactly what we were looking for. The description and photos were on point. Wonderful secluded and peaceful place for a romantic getaway, or for a small family. Hope to come back again soon in the near future.
Guest favourite
Cabin in Brookline
5 out of 5 average rating, 53 reviews

Last Frontier Log Cabin

EmilyRating, 5 stars3 months ago
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!
Superhost
Cabin in South Londonderry
4.65 out of 5 average rating, 420 reviews

Fernando’s hideaway - XCountry Skiing Cabin

CyrusRating, 5 stars1 month ago
10/10 experience!! Honestly it was so much better than what I expected, they did great on creating a safe / affordable and peaceful spot :)
Guest favourite
Cabin in Jamaica
4.89 out of 5 average rating, 388 reviews

Cabin 7min to Ski Stratton-Wood Stove,Views,DogsOK

NataliaRating, 5 stars3 weeks ago
The cabin was perfect for a cozy weekend getaway! In fact, it was even more lovely in person than the photos. We did some lovely hiking in the area and visited nearby farms. Our dog loved the space and slept like a log after a day of hiking. On the day it rained, we had the best time staying inside, reading, playing games, and listening to music. There are clear instructions everywhere to help make sure everything is used properly. While it was too cold and rainy to make too much use of the outdoor amenities, we were able to easily grill. We hope to come back in the summer to make fire pits and swim in the nearby brook! Overall wonderful stay, it was everything we were looking for.
Cabin in Jamaica
4.83 out of 5 average rating, 47 reviews

Cozy Mountain Getaway

BettinaRating, 5 stars2 months ago
Really enjoyed our stay. Close to skiing. Ashley was a wonderful hostess.

Tiny home rentals with a patio

Guest favourite
Tiny home in Brattleboro
4.95 out of 5 average rating, 199 reviews

"Mountain View" Rustic Cabin Retreat w/Fireplace

WilliamRating, 5 stars2 weeks ago
Our stay at the Mtn View cabin was great! Everything was very clean, and despite the colder weather, the cabin was nice and warm thanks to a well stocked pellet stove. We were pleasantly surprised to have a double burner stove instead of the advertised single burner. That made cooking breakfast a bit easier! Sean and crew were very responsive anytime we had questions. I would definitely recommend to anyone looking for a quiet getaway from the city.
Guest favourite
Tiny home in Brattleboro
4.94 out of 5 average rating, 161 reviews

“Hickory” Rustic Cabin Retreat with Fireplace

NatalieRating, 5 stars3 weeks ago
Had a solo trip the cabin was super clean it is dog friendly and I was surprised that there wasnt even any dog hair on the furniture. Host was on property and super nice. Place was very quiet and peaceful. Local restaurants and shops were nice. It does rain a lot and can get pretty muddy but i just took my shoes off when i went inside. Hot tub is clean and plenty of bathroom options.
Guest favourite
Home in Jamaica
4.83 out of 5 average rating, 69 reviews

Rooted Moon Retreat…Sun filled cabin in the forest

GauravRating, 5 stars14 months ago
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!
Guest favourite
Tiny home in Brattleboro
4.87 out of 5 average rating, 214 reviews

“Sugar Maple” Rustic Cabin Getaway with Fireplace

ColtonRating, 5 stars2 weeks ago
Great quiet getaway for April VT weather
Guest favourite
Cabin in Winhall
4.91 out of 5 average rating, 64 reviews

A frame cabin with Hot tub near Stratton, VT

ErinRating, 5 stars1 month ago
The cottage was just what we were looking for for a romantic weekend away. The house was cozy and well stocked and the area had lots to do from shopping, to hiking, and dining!
Guest favourite
Tiny home in Newfane
4.94 out of 5 average rating, 64 reviews

Riverside Wellness Escape: Cold Plunge & Sauna!

JohnRating, 5 stars1 week ago
Absolutely stunning place to stay. Fell asleep to the sound of the river below at night and woke by jumping in it every morning. The sauna was amazing. Perfect for relaxing and unplugging. Location is close to tons of fun places. Restaurants with great food or hiking trails with beautiful views and waterfalls.
Superhost
Tiny home in Wilmington
4.81 out of 5 average rating, 43 reviews

The Pines Cabin | New Tiny Home Near Mt Snow!

TomRating, 5 stars2 months ago
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.
Guest favourite
Campervan/Motorhome in Stratton
5 out of 5 average rating, 14 reviews

Bambi Inn Jamaica

GaryRating, 5 stars2 months ago
The Bambi Inn is absolutely perfect for what it is. Impeccably maintained, on a beautiful piece of property and very convenient for a more cost effective ski weekend lodging. We had some hiccups but we were able to navigate them. It was a very special getaway for myself and two daughters (age 7 and 8). Highly recommend.

Tiny home rentals with outdoor seating

Top guest favourite
Tiny home in Jamaica
5 out of 5 average rating, 11 reviews

Stratton, 5 min. Pikes Falls, 1 min. Fire pit

RitaRating, 5 stars6 months ago
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.
Guest favourite
Home in Wilmington
5 out of 5 average rating, 11 reviews

Outdoor Enthusiasts Paradise!

EmilyRating, 5 stars3 months ago
Our family had a beautiful, peaceful ski/snowboard vacation at Samantha’s home. The house was exceptionally clean and Samantha was an attentive host. We’ll hopefully visit again!
Top guest favourite
Chalet in Jamaica
4.98 out of 5 average rating, 258 reviews

Vermont Chalet

MichaelRating, 5 stars1 week ago
I had a blast in the beautiful Chalet. Everything was what I was expecting and more. The review matched the property and vibes. From the beautiful views outside to the cozy vibes in the loft upstairs, it was amazing. I had a couple of questions for Jason and he answered insanely quick and was very helpful with his information. The Pac-Man was a great addition too. P.S 24,910 is my high score!! I totally recommend and might even come back some time in the future. The host, cabin, property, and area was delightful, nothing but love for this stay!!
Superhost
Cottage in Chesterfield
5 out of 5 average rating, 3 reviews

Cottage on Spofford Lake “Barn”

ChristopherRating, 5 stars6 months ago
The cabins were terrific. We had three cabins as a group. They are across the street from Spofford Lake, which has a small beach and a dock. We had a terrific night hanging out on the beach while lighting a fire in the pit. We had a great visit at Copper Cannon Distillery (located down the road) and went on a few hikes.
Superhost
Cabin in Jamaica
4.89 out of 5 average rating, 161 reviews

Jamaica Mod A Frame

JeffreyRating, 5 stars1 month ago
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.
Superhost
Guest house in Brattleboro
4.91 out of 5 average rating, 517 reviews

Mahalo Temple Retreat

LeoRating, 5 stars2 weeks ago
The Mahalo temple was a home away from home. Cozy place to relax and unwind with plenty of amenities. We had wet snowy weather which kept us away from the hiking we planned for the trip, but the bnb was a respite from the cold.
Top guest favourite
Cabin in Winhall
4.96 out of 5 average rating, 347 reviews

A-Frame Mountain Retreat near Manchester

LeahRating, 5 stars4 days ago
Monique and Jason’s A-Frame cabin exceeded our expectations! They thought of every little detail you would need in a home away from home. The decor was great, the kitchen was stocked with so many utensils and gadgets (I was not expecting to find a zester for my dinner recipe but it was there!) and the bath towels were amazingly oversized, which is a rare find! The A-Frame was the perfect spot for a girls weekend. We loved the record player (especially Alanis and Noah Kahan) and had a great time celebrating our dog Harley’s 9th birthday pawty there. Would highly recommend and can’t wait to stay again!
Guest favourite
Tiny home in Townshend
4.98 out of 5 average rating, 63 reviews

Cheerful cabin retreat in the woods and mountains

CarinaRating, 5 stars1 month ago
My pup and I had a great escape from Boston, and this cabin was the perfect place to land and take in the beautiful scenery outside every window. The screened-in porch and lofted bed are adorable, and my pup and I loved the wood stove. The cabin is equipped with everything, there is a store nearby, and it had a lot of convenient dog items as well. I was glad that I had my Subrau on the mountain roads since it was a rainy weekend. Thanks so much!

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