Tiny house vacation rentals in Windsor County

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Top-rated tiny house rentals in Windsor County

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

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Top guest favorite

A modern ensuite bathroom features a spacious double shower with dual rainfall showerheads and elegant black fixtures. Two built-in benches and a large window offer natural light and a view of the surrounding landscape. White subway tiles create a clean, contemporary look.

Tiny home in Fairlee

5 out of 5 average rating, 131 reviews

Private, 1 bedroom boutique tiny home

This boutique tiny home is situated in the picturesque Upper Valley of Vermont. The nearly 50 acres of private land is equal parts woods and water. You will wake to the mooing of dairy cows. Have your coffee on the porch while watching birds dive for their breakfast on the pond. Inside you will find every modern amenity. A fully appointed chef's kitchen. A living area filled with comfy furnishings and a cozy fireplace. Upstairs is a queen bedroom with an ensuite double showered bathroom. Heaven!

Superhost

An aerial view captures the Honey Pond Treehouse nestled among lush greenery, overlooking a tranquil pond. Rolling hills and distant mountains provide a scenic backdrop, as the sky glows with warm hues from a setting sun.

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

A wooden deck is featured in the foreground, leading to a small sitting area with a patterned chair beside a black side table. Lush greenery surrounds the space, providing a natural setting, while a gravel path and stacked firewood are visible in the background.

Tiny home in Clarendon

4.9 out of 5 average rating, 225 reviews

Secluded tiny house resort - DOG FRIENDLY

New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

Top guest favorite

A spacious outdoor deck features a mix of seating, including lounge chairs and a table set for two. String lights are elegantly draped above, providing a warm glow. Surrounding trees add to the natural setting, enhancing the peaceful atmosphere.

Cabin in Stockbridge

4.95 out of 5 average rating, 107 reviews

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

Guest favorite

A rustic cabin is nestled among the trees, showcasing its wooden exterior and a metal roof. Tall windows allow natural light to fill the space. Surrounding greenery, including ferns and bushes, adds to the secluded atmosphere. A stone wall and picnic table can be seen in front.

Cabin in Sharon

4.92 out of 5 average rating, 262 reviews

Cozy secluded ‘birds nest’ off-grid cabin

Back to basics living, simple rustic charm, circa 1900 cabin in the woods getaway, spend time in nature surrounded by forest, brook, wildlife, hiking trails, fall foliage. Close to Woodstock and S. Royalton, fully off-grid. No electricity or plumbing, yet lanterns and fresh water jugs provided. Unwind from the outside world and reconnect with your self or your loved ones and the natural world around you. Loft with real beds, well stocked kitchen, propane oven, grill, outhouse, Glamping!

Top guest favorite

A wooden boardwalk extends over a tranquil pond, surrounded by lush greenery and tall grasses. Bright flowers bloom nearby, adding color to the natural setting. Sunlight reflects gently on the water's surface, creating a serene outdoor atmosphere.

Cabin in West Windsor

4.97 out of 5 average rating, 242 reviews

Sunset Cabin - your private romantic hideaway

Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just minutes from Mt. Ascutney's hiking/biking trails and in the middle of fantastic cycling country. Near local race including the VT100, Vt overland, VT50. Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring VT!

Guest favorite

The exterior of Bearfoot Cottage is highlighted, featuring a combination of wood and metal finishes. A spacious deck with steps leads to the entrance, framed by large windows. A fire pit sits nearby, complemented by comfortable seating arrangements on the gravel surface.

Tiny home in Chester

4.99 out of 5 average rating, 134 reviews

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Tiny living at its best! Welcome to Bearfoot Cottage, a custom-designed Tiny House escape nestled on 15 acres in Southern Vermont. Enjoy the entire property to yourself with hot tub, Char-Griller BBQ, & Solostove firepit. Hike or snowshoe Ladybug Trail to our babbling brook. Then explore the best of Okemo Valley all at your fingertips! Ski/Snowboarding (+more Winter sports), biking, hiking, fishing, dining, breweries, and live music/nightlife. Your vacation is what you make it!

Top guest favorite

A charming cabin constructed from natural materials is nestled among lush trees in a forested area. Sunlight filters through the leaves, casting dappled shadows on the ground. The cabin features large windows that invite the surrounding greenery inside.

Tiny home in Hartland

4.96 out of 5 average rating, 186 reviews

Cabin on the Hill

Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

Guest favorite

A cozy cabin is presented in a snowy landscape, featuring wooden exterior walls illuminated by warm lighting. Large windows allow glimpses of the interior, where a comfortable sleeping area and a kitchenette are visible. Snow blankets the surrounding trees and ground, enhancing the serene winter setting.

Cabin in Royalton

4.94 out of 5 average rating, 301 reviews

Scandinavian design Cabin w/ private hiking trail

*NEW FROM JULY '24: a Goodland Wood Burning Hot Tub* Welcome to our charming cabin nestled in the heart of the woods, where comfort meets tranquility. This 400 sq. ft retreat is bathed in natural light, boasting high-quality appliances, strong WiFi and thoughtfully curated design furniture to ensure a cozy and memorable stay. Conveniently located near several ski resorts (Saskadena 6, Killington, Stowe) , the pristine White River, and picturesque villages like Woodstock, VT.

Guest favorite

A cozy cabin is nestled among the trees, showcasing a rustic wooden exterior with large windows. It overlooks a gentle slope covered in green grass and wild plants, with sunlight filtering through the canopy above, creating a serene and inviting atmosphere.

Guesthouse in Woodstock

4.98 out of 5 average rating, 241 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

Guest favorite

A newly built tiny cabin is nestled among lush green trees, accessed by a wooden deck leading to a cozy seating area. Natural stones and grass surround the cabin, enhancing its peaceful woodland setting, while warm lights add a welcoming touch.

Cabin in Pittsfield

4.98 out of 5 average rating, 155 reviews

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! MUST have AWD/4x4 for winter access on dirt road and driveway. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the winter beauty Vermont has to offer!

Guest favorite

A spacious living area features a light gray sectional sofa with decorative pillows, facing a large window with natural light illuminating the room. A glass coffee table displays a wooden tray, while a kitchen area is visible to the right, complementing the cozy atmosphere.

Cabin in Rochester

4.95 out of 5 average rating, 466 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

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What guests are saying

1BR mountain view retreat with kitchenette

4.59 out of 5 average rating, 29 reviews1 month ago

I really enjoyed staying at this property. It was the perfect size for a solo trip or a trip with one other person. The views are stunning and the property is quiet and private. Great hiking, good food, and shopping are all very close. The hosts were very responsive and accommodating. They offered free early check in which was great. If you are looking for a relatively inexpensive getaway in a beautiful place, I would highly recommend this property. Just an FYI for anyone that isn’t familiar with driving backroads in Vermont this time of year. March through early June is “mud season.” The road on which the property is located was a bit muddy in parts. It wasn’t anything that my RAV 4 couldn’t handle, but just be careful if you don’t have an AWD vehicle.

Home in Weston

What guests are saying

Sage House at Camp Greenwood Vermont with Sauna

4.91 out of 5 average rating, 35 reviews1 month ago

This tiny house is the cutest and coziest place. Very well made and the decor and vibe were spot on. I absolutely loved it. The sauna is a huge bonus as well. The place is the exact representation of the photos. Overall a very great stay and the hosts were super responsive.

Tiny home in Chester

What guests are saying

Fat Sheep Farm & Cabins - Ascutney Cabin

5 out of 5 average rating, 59 reviews3 weeks ago

Among dozens of trips to Vermont, our stay at Fat Sheep Farm is newly at the top of the favorites list! The location is remote yet not too far from other villages for more dining, grocery and recreation options. The cabin was cute, cozy, clean and included every pan and kitchen utensil needed for cooking in. Delicious pumpkin-chocolate chip scones and a basket of fresh eggs greeted us upon arrival, can’t beat that! On clear nights, the back patio is a great place for star-gazing. The cabin we stayed in, the Ascutney, accommodates pets and we brought our 2 cats on their first vacation. Their views may vary! Suzy and Todd were super friendly and the best part of the stay was tagging along for the morning farm chores, learning about the day to day logistics and, most of all, interacting with all the amazing animals (sheep dog in training, Cocoa, stole my ❤️).

Farm stay in Windsor

What guests are saying

The Cluck House

4.99 out of 5 average rating, 134 reviews6 months ago

Tina and Mike were nice, friendly and welcoming. We enjoyed our stay at Tina’s place and our dog had a great time playing outside as well. We took a lot of beautiful pictures. It is a great location and very peaceful. Tina recommended a Turkish restaurant. They had really good food and coffee.

Tiny home in Woodstock

What guests are saying

Cozy Guest Cabin w/private hot tub and bath

4.81 out of 5 average rating, 62 reviews5 months ago

Very cozy spot whether you're looking for a place to relax or to venture out like myself. Can be a bit noisy at times due to the highway but if you aren't a light sleeper this place is a great spot. Very clean and as advertised and Carl was very responsive and polite.

Guesthouse in Hartland

What guests are saying

Beautiful Cabins in the Mountains

4.61 out of 5 average rating, 23 reviews3 weeks ago

This cabin was a 10/10! I would definitely recommend staying here! It’s the perfect getaway to escape and have a peaceful trip! Bring everything you would need to camp. The gas stove takes some time to heat up but once you get it going the cabin is definitely warm and cozy. We were here during an ice storm and were warm the entire time! It’s also in a great location if you want to ski. Todd is also a very responsive host and super friendly! If you’re considering booking, I would go for it! I would return in a heartbeat.

Farm stay in Plymouth

What guests are saying

Romantic Cabin on Charming Vermont Farm

5 out of 5 average rating, 7 reviews42 months ago

This lovely cabin is really all you could possibly want out of a great nature escape. Amazing natural sunlight, comfy bed, heated outdoor shower, fire pit, and hiking trails right on the property itself. Also within 10mins of Gile mountain which offers breaktaking 360 degree views of the nearby mountains. They were really great hosts, had some great recs for hiking, and had some awesome furry friends on the property. I will definitely be staying here again!

Tiny home in Norwich

What guests are saying

The Vershire Fortress

4.92 out of 5 average rating, 91 reviews1 month ago

What a delight! I was here to get away and write for a few days, and it was exactly what I needed. beautiful views, comfortable, cheerful, and elegant. It has everything you could need, and it was all easy to figure out. The only issue I had was the drive to and from the house bc it is peak mud season and the roads were in rough shape. I was really glad I had the recommended all wheel drive car bc you slide around quite a bit otherwise.

Cottage in Vershire