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

French doors open into a cozy living area where a sectional sofa is visible. A small green table with a bouquet of flowers sits in front, while sunlight illuminates the space. Outside, garden views reveal lounge chairs and vibrant flowers.

Guesthouse in Gloucester

4.96 out of 5 average rating, 272 reviews

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

Top guest favorite

Guest suite in Uxbridge

4.99 out of 5 average rating, 353 reviews

Beautiful, Unique, & Cozy Cedar Flat

Come enjoy this new and beautifully designed space in historic Uxbridge, MA. Set up like a tiny house, it is the most cozy and clean place you will visit. A ship’s ladder will take you to the queen loft bed or use a new PotteryBarn sleeper sofa. The Frame TV will act as a beautiful painting if you prefer to "unplug." Climate control and a hammock chair are a perfect combo! Located on a quiet street, it is an easy 25 min. drive to Providence or Worcester, and only 50 min. to downtown Boston.

Top guest favorite

A vibrant sunset is captured over a tranquil lake, with the horizon presenting rich hues of orange and yellow against a backdrop of wispy clouds. Silhouetted tree foliage frames the scene, enhancing the peaceful ambiance as the sun descends beyond distant mountains.

Guest suite in Tyngsborough

4.98 out of 5 average rating, 247 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Located on a lovely small lake with a panoramic view from the bedroom, private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room-so not an 'entire' home but more than just a room! Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park mills, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants and tax-free shopping. 1 hr from Boston and near many New England highlights.

Guest favorite

An inviting living area features vaulted wooden ceilings and large windows showcasing views of the surrounding nature. A modern wood-burning fireplace is prominently positioned, complemented by comfortable seating. Natural wood flooring adds warmth to the space, creating a cozy and open atmosphere.

Chalet in Otis

4.94 out of 5 average rating, 418 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

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, 365 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.

Guest favorite

Bungalow in Dartmouth

4.95 out of 5 average rating, 176 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!

Top guest favorite

A serene sunset can be seen over calm waters, with the sun rising behind a lighthouse. The sky transitions from orange to soft pink and light blue, while the lighthouse stands silhouetted against the horizon, creating a peaceful coastal scene.

Cottage in Plymouth

4.94 out of 5 average rating, 270 reviews

Ocean View Cottage

Charming cottage with an ocean view in a private setting seaside community with updated kitchen that does NOT include a stove however there is a cooktop, microwave and toaster oven, 3/4 bathroom w a shower. Firestick/RokuTV. It is ONE room, open concept with a comfortable memory foam easy fold out king couch. The cottage is separate from the house and has its own entrance w own parking for 2 cars. 1 mile from the beach and 5 miles from downtown. **PLEASE NOTE ONLY 2 PERSON OCCUPANCY**!!

Guest favorite

An open door reveals the entryway of a rustic cabin. A patterned rug leads into a softly lit interior, where a cozy bed is visible in the background, framed by natural wood accents and windows that invite the outside in.

Cabin in Cummington

4.98 out of 5 average rating, 216 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Top guest favorite

The entrance to the Bridge of Flowers is showcased, featuring a decorative sign surrounded by vibrant floral landscaping. Pathways lined with plants and stones lead into the serene area, while a lamppost adds to the charming ambiance. The setting is tranquil and inviting.

Apartment in Shelburne Falls

4.98 out of 5 average rating, 562 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Top guest favorite

An inviting entryway is showcased, featuring a warmly decorated door and charming wooden accents. A blue chair sits beside a small table, complemented by a vibrant area rug. Surrounding plants add a touch of greenery, enhancing the welcoming atmosphere of the tiny house retreat.

Place to stay in Wellfleet

4.97 out of 5 average rating, 239 reviews

Romantic Cape Cod Tiny House + Hot Tub

Welcome to the Romantic Hideaway, our magical, secluded tiny house nestled between lush gardens and the woods alongside our property. Just a short drive to ocean beaches and freshwater ponds, and a pleasant walk to the quaint center of Wellfleet. Wake to birdsong and enjoy fresh muffins on your sunny, private deck. Your stay includes access to our Magnolia Spa with hot tub and sauna (June+); massage is available in July at special guest rates. A sweet, quiet escape on the Outer Cape.

Top guest favorite

A weathered wooden barn displays the sign 'Milestone Farm,' illuminated by the soft evening light. The rustic texture of the wood is showcased, reflecting the farm's charm. Nearby elements, such as a mailbox, add context to the property’s welcoming environment.

Tiny home in Northampton

4.99 out of 5 average rating, 204 reviews

Tiny House Farm Retreat: Mountain Views, Fire pit

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.

Guest favorite

Lush greenery surrounds a flowing river, with vibrant green leaves overhead and ferns lining the banks. The water can be seen gently moving over rocks, creating a peaceful natural setting in the woods.

Treehouse in New Marlborough

4.91 out of 5 average rating, 129 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.