Tiny house vacation rentals in Connecticut River

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Top-rated tiny house rentals in Connecticut River

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

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Top guest favorite

A modern cabin exterior is framed by fresh snow, showcasing large picture windows that invite natural light. Outdoor seating is visible beside a fire pit, surrounded by a peaceful winter landscape of trees blanketed in snow.

Tiny home in Dorchester

4.99 out of 5 average rating, 142 reviews

Trailside Stays - Tiny House in the Woods-Blue Jay

This charming and elegant little cabin will transport you into nature. The feeling of camping outdoors with indoor amenities. Part of the brand-new campsite, Trailside Stays that is conveniently located alongside the ski and mountain bike trails at Green Woodlands. This tiny house features 1 high quality queen-size bed, linens, kitchenette, large picture windows, bathroom with shower, heating and A/C, outdoor seating and grill top fire pit. Don't see your dates available? Check the other cabins!

Superhost

Tiny home in Bennington

4.92 out of 5 average rating, 243 reviews

Ski, Hot tub, Hike & MORE at Waterfront Tiny House

Waterfront oasis. Relax in fully equipped Tiny House with wifi, cable tv, bath & shower tucked in a private wooded setting overlooking a small waterfall in nature's paradise on Powder Mill Pond and Contoocook River. Hike, Swim, Fish, Kayak, Canoe, Paddle boat. Private fire pit. Hot tub. Eclectic dining, 4 golf courses, shops, breweries, skiing all nearby. Just outside of Peterborough in Southern New Hampshire, only 1.5 hours from Boston or 2.25 hrs. from Hartford in legendary Monadnock Region.

Guest favorite

A small, red tiny house is set against a backdrop of lush trees. A white deck with an umbrella offers a shaded outdoor space. Steps lead up to the entrance, showcasing the charming design and inviting surroundings.

Tiny home in Canton

4.9 out of 5 average rating, 109 reviews

Tiny House On Wheels!

The Tiny House is a great getaway close to the Western Mountains of Maine. Auburn, Augusta & Farmington are also close by. It has a sleeping loft upstairs with a full size foam mattress and a day bed downstairs with a twin foam mattress. It’s on two acres, two lakes nearby great for fishing, boating & swimming. Sunday River Ski Resort is just 45 minutes away. The Tiny House has a small fridge/freezer, microwave, toilet, shower, heat/AC & deck to relax on Please Note: No cooking in the house.

Superhost

A tranquil view of Dudley Pond is captured, showcasing calm waters reflecting the clear blue sky. Lush greenery borders the pond, with a distant house visible among the trees. A gentle ripple is seen in the water, suggesting a serene atmosphere.

Home in Wayland

4.78 out of 5 average rating, 486 reviews

Tiny house experience steps from the water!

-Tiny house experience in quiet private neighborhood on its own lot with great backyard & fire pit on private secluded St. -prof cleaned after each guest -High speed internet/ expanded cable -Built in full bed with queen sleeper futon bed that can sleep 2 more -Just a few steps from beautiful Dudley Pond for swimming/fishing and great walking trails Wayland is one of nicest towns in MA yet only a min or two from anything you need and less than half hour from Boston. texts returned instantly

Superhost

A tiny house with two solid glass walls is nestled among tall trees, surrounded by vibrant green foliage. The sunlight filters through the leaves, illuminating the natural forest floor, covered in a mix of earthy tones and scattered greenery.

Tiny home in Jay

4.93 out of 5 average rating, 229 reviews

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak

Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $150.

Top guest favorite

A tiny house is nestled in a wooded area, surrounded by trees. A gravel parking area is visible alongside it, with a fire pit and seating arranged nearby. A propane grill rests on the patio, and an umbrella provides shade over a table.

Tiny home in Wallkill

4.99 out of 5 average rating, 287 reviews

Get Away to "Hygge" Tiny House on 75 Private Acres

Escape to 75 acres of secluded, private land and lounge in this "hyggelig" tiny house. The house has everything you need, from heat and A/c, strong wifi, TV with streaming (sign in to Netflix, HBO, etc), full working kitchen (gas stove, oven, microwave), shower and bathroom. This tiny house has an incredible amount of light coming in from the very large windows throughout. Outdoor amenities include wood patio, propane bbq grill, dining table/chairs, fire pit. Lawn games available on request.

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, 226 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.

Superhost

Two striped chairs are positioned on a manicured lawn, overlooking the calm Upper Delaware River. Lush greenery surrounds the area, with trees lining the riverbank. Smooth stones lead down to the water, creating a serene setting ideal for relaxation and enjoying nature.

Tiny home in Barryville

4.78 out of 5 average rating, 102 reviews

Tiny House on Gorgeous Private Riverfront Property

Our private tiny home is on a 1/3 mile of beachfront property with private access along the pristine Upper Delaware River, located on the scenic national byway. The Delaware River Valley runs right between the Catskill and Pocono Mountains. Our quaint hamlet of Barryville, NY offers antique shops, Farmers' market, local restaurants, and is close to other river towns, and Bethel Woods Performing Arts Center, the original Woodstock site. "A Nature, Community, Arts and Culture Lover's Paradise"

Guest favorite

A charming tiny house built from warm wood is nestled among trees in a wooded area. A wooden bridge leads to the porch, enhancing access. Surrounding foliage displays rich autumn colors, creating a natural atmosphere of tranquility.

Tiny home in Wilmington

4.94 out of 5 average rating, 305 reviews

Tiny house in the Adirondacks!

This tiny house located in the Adirondacks in Wilmington, New York is cozy, cute and comfortable! It is convenient for many Adirondack activities including all types of biking, hiking, ,fishing, swimming, leaf peeping or just a quiet getaway. It is just minutes from Whiteface Mt. and a growing network of mountain bike trails. Ten miles to the beautiful village of Lake Placid .This tiny house is equipped with a kitchen, fire pit, and outdoor bathroom . Sleeps 3 adults comfortably.

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, 135 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!

Guest favorite

A tiny home sits under a clear night sky, featuring warm wooden siding and a well-lit entrance. A cozy fire pit is surrounded by a lounge chair and a hammock nearby. An umbrella provides shade to the outdoor seating area.

Tiny home in Worcester

4.9 out of 5 average rating, 101 reviews

Fall Foliage and Tiny Home Glamping @ Maia's Place

Enjoy a true Tiny Home Glamping experience at Maia's Place! Located only 20 minutes from Cooperstown and baseball fields. Enjoy beautiful views of the mountains all around. This tiny home sits on a private two acres, has an outdoor patio area for lounging, grilling, and star gazing at night. The inside is fully equipped with a convection stovetop, fridge, bathroom, wifi hotspot, and queen-sized bed with a 5x5 east-facing picture window to capture the perfect sunrise!

Guest favorite

A modern bathroom vanity is featured, showcasing a white countertop with a sleek sink and contemporary faucet. The cabinetry below offers storage space, while a large mirror reflects the light and enhances the room’s ambiance.

Tiny home in Au Sable Forks

4.88 out of 5 average rating, 121 reviews

Modern Tiny House

Charming oasis in the quaint Village of AuSable Forks centrally located 30 mins either to Lake Placid or Plattsburgh NY. Located 20 mins from Whiteface Mountain/15 mins to AuSable Chasm. Walking distance to town including deli, pizza place, grocery store, local pub and of course fishing on the AuSable River. Short drive to tons of hiking, boating, mountain biking and skiing and all that the Adirondacks has to offer.