Tiny house vacation rentals in Windsor County

Find and book unique tiny house rentals on Airbnb

Top-rated tiny house rentals in Windsor County

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A set of glass doors opens to a spacious outdoor area featuring a stone fire pit surrounded by blue chairs. Lush greenery forms the background, enhancing the tranquil setting. Natural light streams in, highlighting the inviting atmosphere of the space.

Tiny home in Clarendon

4.9 out of 5 average rating, 228 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.

Guest favorite

A private boat is seen docked at a wooden pier, surrounded by lush greenery. The calm river reflects the surrounding trees, creating a serene scene. Light filters through the foliage, enhancing the peaceful atmosphere of the waterfront.

Guesthouse in Springfield

4.85 out of 5 average rating, 373 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Top guest favorite

A rustic cabin is nestled among trees, featuring a spacious outdoor deck. Red accents frame the entrance, and steps lead down to a fire-pit area surrounded by green grass. The expansive views of the surrounding mountains are visible in the background.

Cabin in Stockbridge

4.95 out of 5 average rating, 109 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.

Top guest favorite

The rustic cabin, surrounded by lush trees, features a porch with a picnic table. The wooden structure is designed with a gabled roof and large windows, providing a welcoming entrance. Flower boxes adorn the front, enhancing the natural setting.

Cabin in West Windsor

4.97 out of 5 average rating, 249 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

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, 265 reviews

‘Bird Nest’ cozy majestic off-grid retreat w/sauna

Secluded rustic charm, circa 1900 cabin in the woods getaway, spend time in nature surrounded by forest, brook, wildlife, hiking trails, fall foliage, mountain biking skiing. Sauna, Cold Plunge, Outdoor Shower & Hot Bath. 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, grill, outhouse, Glamping! Close to Woodstock, VT and South Royalton, 30 mins to Killington VT or Hanover NH

Top guest favorite

The loft area is adorned with a colorful quilt laid over a spacious bed. Wooden walls and a sloped ceiling create a warm atmosphere, while a window offers natural light and views of the surrounding nature.

Tiny home in Hartland

4.96 out of 5 average rating, 193 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.

Top guest favorite

A wooden deck features a small round table and two chairs, surrounded by lush greenery. A fire pit area with seating is visible below, nestled among the trees, providing a peaceful outdoor gathering spot.

Home in West Windsor

4.98 out of 5 average rating, 124 reviews

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Top guest favorite

A cozy living room area features a comfortable sofa and a coffee table centered on a patterned rug. Natural light floods in through sliding glass doors that lead to an outdoor deck, showcasing the surrounding greenery. Decorative wall art and a small desk add character to the space.

Cabin in Mount Holly

4.98 out of 5 average rating, 245 reviews

Private Cabin/PetsOK/Minutes to Okemo/AC/Fast Wifi

Enjoy the beauty of Vermont at our private cabin. Situated on acres of woods next to a small creek, the cabin is 15 minutes to Okemo Mountain, excellent hiking on the Appalachian Trail and scenic Vermont towns for dining and shopping. With a queen bed loft, a double bed bedroom and a pull out sofa, the cabin sleeps up to 4 people. The kitchen is nicely equipped and there is a charcoal grill outside. High speed fiber optic internet will keep you connected. Max 2 pets allowed.

Guest favorite

A wooden deck extends from the guest house, surrounded by tall trees and lush greenery. Sunlight filters through the leaves, casting dappled shadows on the floor. A gentle stream can be seen flowing nearby, adding to the tranquil ambiance of the setting.

Guesthouse in Woodstock

4.98 out of 5 average rating, 242 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

The interior of the cabin features warm wooden beams and flooring, creating a cozy atmosphere. A comfortable blue sofa is positioned next to a wooden coffee table. A spiral staircase leads to a lofted area, while large windows allow natural light to fill the space.

Cabin in Pittsfield

4.98 out of 5 average rating, 157 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

The kitchen area features modern cabinetry with open shelving displaying various dishware and utensils. Stainless steel appliances, including a stove and refrigerator, are present. Natural light floods the space through a window, illuminating the bamboo floor with a woven mat underneath.

Cabin in Rochester

4.95 out of 5 average rating, 472 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.

Guest favorite

A tranquil outdoor scene is depicted, featuring neatly hung fabrics catching the sunlight against a backdrop of lush green hills. The well-maintained lawn is surrounded by vibrant plants, with the silhouette of a large tree providing shade in the distance.

Tiny home in Woodstock

4.99 out of 5 average rating, 135 reviews

The Cluck House

The Cluck House (360sq. ft) was converted from a chicken coop into a 1 bedroom guest space in the 1950’s. Today it is still used for extra sleeping quarters during the warmer months (May 15-Oct 15). Please Note: The Private Full Bathroom Is Located In The Main Farmhouse, just a short walk across the lawn. We are pet friendly and welcome guests who wish to travel with them. We charge a $35 Cleaning Fee per trip.