Tiny house vacation rentals in Massachusetts

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Top-rated tiny house rentals in Massachusetts

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

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Guest favorite

A light-filled living area features a white sofa and a comfy wicker chair, arranged around a wooden coffee table. The space is adorned with soft blue accents, a textured area rug, and a piece of artwork, contributing to a cozy and inviting environment.

Tiny home in Dennis Port

4.82 out of 5 average rating, 475 reviews

★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes

Welcome to SAND PEBBLE COTTAGE! We are PET FRIENDLY! ($25/nt) This 300sq.ft "TINY HOUSE" is 0.4 mi from the ocean beach & 1/2 mi from Dennisport village At the end of a cul-de-sac, this tiny cottage has everything you need ✅ 4/10mi to beach & village ✅ Kitchen w/marble counters ✅ 2 Bike ✅ Deck w/furniture & charcoal BBQ ✅ Parking-2 cars ✅ Separate bedroom ✅ Full A/C ✅ Bring your sheets/towels-we do not provide linens ✅ Pet friendly-only 1 pet as the cottage is tiny $25/nt

Top guest favorite

A serene dock extends over tranquil waters, surrounded by lush greenery. Soft lighting illuminates the path and seating area, creating a peaceful ambiance for evening relaxation. The setting invites reflection and appreciation of the natural surroundings.

Cabin in Littleton

4.99 out of 5 average rating, 169 reviews

Private & Remote, Enjoy Outdoors, Sleep in Luxury

Bit of a wonderland (57 Acres, 100+ 5-star reviews). A place you won't soon forget. Complimentary firewood, 1/2 hour from Boston, camp but sleep in luxury. This cabin is privately located on a retired Christmas tree farm, about a one-quarter mile off the public road. Listen to the water flow, and watch the sunset over the wetlands. This site is ideally suited for a couple looking for an outdoor experience retiring to the comfort and security of a luxury tiny house. Everything is solar-powered.

Guest favorite

A whimsical tower with a conical roof is framed by lush greenery. A stone path leads to an intricately carved wooden door, surrounded by seasonal flowers. Natural stone and rustic wood elements enhance the enchanting garden setting.

Tiny home in Tyringham

4.97 out of 5 average rating, 356 reviews

Enchanted Tiny Tower nestled in the Berkshires

Whimsical and romantic tower on the Santarella Estate in Tyringham, MA in the heart of the Berkshires. Live out your fairytale in this two-story unique, tiny home. First floor offers 3 rooms in one with kitchenette, sitting area, and dining room looking out on to the babbling brook. Upper bedchamber with canopied bed provides amazing views of sky and trees through massive, mill windows. Perfect destination for a relaxing getaway or special stay while exploring all the Berkshires has to offer.

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

Guest favorite

Bungalow in Dartmouth

4.95 out of 5 average rating, 174 reviews

Updated Vintage Bungalow with Incredible Views

This space has been fully updated in the spring of 2020. Incredible unobstructed panoramic views. It is 400 sq' with an additional 350 sq ' of living space on the deck. The neighborhood is quiet, but you are a stones throw from I-195, making places like Boston, Providence and the Cape and Islands very easy to get to. The décor is bright and funky! Close to UMASS. Extensive custom area and house guide is at the Bungalow with everything you need to know to maximize your experience in the area!

Guest favorite

A serene lake scene is framed by lush greenery, with gentle mist rising from the water at dawn. Soft hues of orange and pink illuminate the sky, reflecting on the calm surface of the lake. A grassy area leads to the water's edge.

Tiny home in Holland

4.96 out of 5 average rating, 101 reviews

C. Chief Cook delightful tiny house

Enjoy peaceful surroundings of this rustic destination. Come relax at this former camp under renovation. Hang out by Lake Siog where you can paddle board, kayak, use the rowboat, find a meditation site, light a campfire or just rock on the hammock. Lake Siog has a number of hiking and biking trails and the Quinebog River Canoe Trail. We are close to the Brimfield Antique Flea Market, Palmer Antique Co-ops, Old Sturbridge Village and restaurants, wineries, and breweries like Treehouse Brewery.

Superhost

The interior features a combination of wooden textures and colorful wall panels. A staircase leads to the sleep loft, while a kitchenette area includes a small coffee station. Decorative elements, such as a wall sign and a fire extinguisher, are also visible.

Tiny home in Pembroke

4.85 out of 5 average rating, 104 reviews

Tiny farm house on horse farm

Set in a quiet cul-de-sac at the end of our driveway, this tiny house is part of our family compound and working horse farm. We have and many animals. Enjoy your space, knowing we are just 50 yards away should you need anything. This is a true tiny house experience. The kitchenette has everything you need. The sleep loft is accessible by a ladder and has a low ceiling. Disclaimer there is no door on the toilet, which is tucked away in the kitchen area. WiFi connection is not guaranteed.

Top guest favorite

A charming tiny house is nestled among tall trees, featuring a wooden porch with steps leading up to the entrance. Vibrant stained glass windows and warm wood tones enhance the inviting appearance, while natural light filters through the surrounding foliage.

Tiny home in Wellfleet

4.98 out of 5 average rating, 302 reviews

Magical Writers Cabin + hot tub in Wellfleet Woods

Escape to our unique Writer’s Cabin in the peaceful woods of Wellfleet—a magical retreat that feels like you're staying in a treehouse! You'll be surrounded by nature yet just minutes' drive from stunning beaches, crystal-clear ponds, scenic trails, and a short stroll to charming Wellfleet harbor and quaint town center. Relax and unwind at our brand-new Magnolia Spa (opening in June), featuring a hot tub and sauna. On-site massage therapy begins in July—ask us about exclusive guest rates!

Top guest favorite

A compact bathroom features a wall-mounted sink with a black faucet and a circular mirror above it. Soft beige curtains hang next to a shower area. A woven basket holds neatly rolled towels, while natural wood accents complement the light-toned wooden walls.

Tiny home in Northampton

4.98 out of 5 average rating, 186 reviews

Tiny Home Retreat

The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.

Superhost

An outdoor view illustrates the surrounding landscape of the tiny house, featuring a gravel path leading to a wooden structure. Lush greenery and towering trees create a serene setting, with a patio area visible in the background that includes seating for outdoor dining.

Tiny home in Edgartown

4.87 out of 5 average rating, 147 reviews

Unique Vineyard Tiny House “The Banana Stand”

A Martha’s Vineyard tiny house perfect for a relaxing trip to the island. Included with a parking spot and private entrance, this tiny house has the privacy and amenities you need for an island getaway. Located just 2-miles from all the shops and dining that downtown Edgartown has to offer, staying in "The Banana Stand" provides full use of the kitchenette, bathroom, outdoor shower, sofa bed, wifi, outdoor fireplace, and grill. Vineyard uniqueness meets tiny house comfort.

Guest favorite

The exterior of a rustic double treehouse is visible, surrounded by tall trees and lush greenery. The structure features weathered wood and spacious deck areas with steps leading up to the entrance. Warm light emanates from the windows, hinting at a cozy interior.

Treehouse in New Marlborough

4.91 out of 5 average rating, 122 reviews

Double 3 Bedroom Tree House in the Berkshires

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

Guest favorite

A covered porch area features wicker seating with decorative cushions, inviting relaxation. A small table is positioned between the chairs, with a view of a landscaped yard visible through the railing. Potted flowers add a splash of color, enhancing the outdoor ambiance.

Cottage in Provincetown

4.81 out of 5 average rating, 474 reviews

Private cottage green friendly and pet friendly

. Private quiet Restored and renovated stand alone cottage in the west end location complete with new renovation of kitchen and bathroom. Recently added an Extended bay window, new skylight, and brand new dishwasher Green friendly and pet friendly From June 28 to September 10 this is only a Saturday to Saturday rental only . Bear week and carnival week is a surcharge of $50 more per night. When you bring a pet there is a separate cleaning fee of $40 non refundable