Vacation rentals in Sunderland

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Top-rated vacation rentals in Sunderland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.95 out of 5 average rating, 152 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Top guest favorite
A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.
Chalet in Otis
4.95 out of 5 average rating, 481 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

Top guest favorite
The exterior of a Dutch Colonial farmhouse is showcased, featuring a symmetrical design with multiple windows on the upper level. Neat landscaping accentuates the front yard, including well-maintained shrubs. A vibrant tree is visible to the left, adding color to the inviting setting.
Home in Sunderland
4.98 out of 5 average rating, 61 reviews

Farmhouse on working dairy farm

Spacious and charming Dutch Colonial farmhouse on a family- owned, active dairy farm. Located in Sunderland's historic district, it has access to great dining, hiking trails on Mt. Toby, the Connecticut River, and is a short distance from Amherst and the Five College Area. This beautiful home features a recently remodeled kitchen, four large bedrooms, dining and living rooms, office, and a lovely screened-in porch with gorgeous views of Mt. Sugarloaf, farm fields and the Connecticut Riverbank.

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 397 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite
A comfortable sleeping area is furnished with a spacious bed, layered with light bedding. A sectional gray sofa is positioned nearby, providing additional seating. Natural light fills the room, highlighting the clean, modern decor. A doorway leads to another room, expanding the suite's layout.
Guest suite in Sunderland
4.99 out of 5 average rating, 164 reviews

Bright private suite mins. from Five College area

Welcome to our bright, newly renovated suite in the historic Elihu Smith home, built in 1847. Centered on historic S. Main Street in Sunderland, we are minutes from UMass, Amherst, Hadley, Deerfield, and located on the local bus route connecting directly to UMass and Amherst. Ideal for stays of any length of time, for business or pleasure during any time of the year and walking distance to the Millstone market, as well the Bridgeside Café. Suite is professionally cleaned between each stay.

Top guest favorite
Guest suite in Village of Pelham
4.99 out of 5 average rating, 170 reviews

Under the Hemlocks – Boutique Retreat – Amherst

Escape to a private bijou guest suite under the hemlocks—a refined, scent-sensitive retreat, small and elegant by design. Enjoy a deep clawfoot soaking tub, private courtyards with bistro dining and fire pit, plus a unique off-grid screened garden sanctuary—the Writer's Retreat. Under the Hemlocks invites you to slow down, unplug and rediscover the simple pleasures—morning birdsong, evenings by the fire, a long soak. Minutes from Amherst, UMass, Amherst College & Emily Dickinson Museum.

Top guest favorite
An expansive view of rolling hills and distant mountains is visible through a treeline, with a foreground of manicured green grass and apple trees. The cabin's wooden structure is partially seen on the right, enhancing the connection to nature.
Cabin in Williamsburg
4.97 out of 5 average rating, 130 reviews

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Top guest favorite
Apartment in Leverett
5 out of 5 average rating, 115 reviews

Forest Hideaway—Light, Privacy, Washer/Dryer

Wake up among 100-year-old trees, then drive 12 minutes into Amherst. Or hike out the door toward wooded trails. The apartment sits with our house on 5 acres of mature forest, high on a hill and facing the woods. With a kitchen & washer/dryer, the apartment is both peaceful and practical, great for a weekend getaway or an extended stay, ideal for academics needing space for contemplation or for a couple visiting family. (Read about the steep driveway if planning a winter trip.)

Top guest favorite
A spacious, two-story dark wooden building is nestled among trees, showcasing a welcoming entrance with a large front porch. Lush green grass surrounds the structure, enhancing its serene setting. Bright blue skies and scattered clouds further complement the inviting atmosphere.
Apartment in Conway
4.96 out of 5 average rating, 220 reviews

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Top guest favorite
The charming exterior of the 18th-century farmhouse features yellow clapboard siding and a classic red front door. Symmetrical windows line the facade, surrounded by a manicured lawn and the shade of nearby trees.
Farm stay in Whately
5 out of 5 average rating, 38 reviews

Beautiful 18th Century Farmhouse

Enjoy the beauty of a bygone era while staying in this 18th-century farmhouse, located on the historic Quonquont Farm property, a working farm and orchard. The building has been lovingly restored with custom raised paneling and antique details, and is beautifully decorated with period furniture. The house overlooks a quiet, maple-lined street in a peaceful and secluded area just minutes from 91.

Top guest favorite
Guest suite in Amherst
4.96 out of 5 average rating, 323 reviews

Sunlit Cozy Cabin 8 Private Acres By Colleges

Escape to this peaceful, sun filled log cabin set on 8 private acres minutes from Amherst center, UMass and Amherst College. With its vaulted ceiling, warm electric fireplace, and views of the surrounding gardens, the cabin offers a cozy retreat. Relax on the spacious deck, unwind by the pool, or explore nearby trails and Atkins Reservoir.

Top guest favorite
A spacious kitchen is equipped with modern appliances and quartz countertops. Ample cabinetry provides storage, while a breakfast bar features comfortable seating. Natural light filters through large windows, highlighting a clean, organized space, perfect for meal preparation.
Home in Sunderland
5 out of 5 average rating, 96 reviews

Sunderland house - 5 College area

Full house in Sunderland in a quiet neighborhood. Close to the Five College area, UMass, Amherst, Mount Holyoke, Hampshire and Smith. Built in 1949 but newly renovated in 2024. Minutes from Yankee Candle and Treehouse Brewery. We welcome all well-behaved dogs, (with prior approval).

Popular amenities for Sunderland vacation rentals