Vacation rentals in Sunderland

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Top-rated vacation rentals in Sunderland

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Top guest favorite

A serene pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.

Cottage in Petersham

4.99 out of 5 average rating, 212 reviews

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Top guest favorite

The spacious studio apartment features a well-equipped kitchen with a countertop and bar seating. Natural light filters through the windows, highlighting wooden cabinetry and modern appliances. The open layout includes a cozy seating area, creating a functional living space beneath sloped ceilings.

Apartment in Williamsburg

4.95 out of 5 average rating, 110 reviews

The cozy clubhouse

Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

Top guest favorite

A cozy studio bedroom features a spacious bed draped with a striped quilt, complemented by a decorative rug. Natural light enters through a window adorned with soft curtains. An art piece hangs above the bed, with a small table and two chairs accommodated nearby.

Guest suite in Greenfield

4.95 out of 5 average rating, 205 reviews

Pristine Oasis with Private Bath

Our studio space (250 sq ft) is separate from the main house and located on the outskirts of Greenfield MA. The location provides easy access to downtown, restaurants, shopping areas and Interstate 91. Modern decor, tiled artsy bathroom, lots of garden art, and sweeping views of Berkshire foothills make this a great choice for foliage season, summer recreation and choice winter skiing. One Queen bed. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to Canada.

Guest favorite

An open living area features a mix of textures with exposed wood beams and a colorful patchwork quilt hung on the wall. A red couch sits across from a decorative rug on tiled flooring, with a wood stove and welcoming chalkboard in view.

Cabin in Sunderland

4.95 out of 5 average rating, 130 reviews

Mt Toby Retreat

Our home in Nature! Post & beam house w/ cabin-like, rustic feel, made of pines milled from forest behind house. Piano for songwriters. Borders state forest w/ trails waterfalls, creeks, caves, old growth forest, lookout at summit, 5000 acres of Mt. Toby... Lots of sugar maples - prime location for leaf peeping. Mon/Tues blocked for cleaning, but message if you want a week stay! 5-10 min to Montague Bookmill, Mt Sugarloaf, Historic Deerfield, 15-25 min to Amherst, Northampton, Greenfield.

Top guest favorite

A serene sleeping area is present, featuring a spacious bed adorned with a patterned duvet. Large windows frame the view of the surrounding trees, inviting natural light into the space. A small bookshelf stands in the corner, complementing the wooden floors and walls.

Cabin in Cummington

4.98 out of 5 average rating, 228 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 bright studio features a cozy sleeping area with a spacious bed, a comfortable yellow armchair, and two plush couches. A coffee table sits in the center, with large windows allowing natural light and views of greenery. A television is mounted on the wall.

Apartment in Shelburne Falls

4.98 out of 5 average rating, 581 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

The exterior of a light blue guesthouse is framed by lush greenery and trees. A distinctive tower is visible atop the building. The setting conveys a sense of seclusion in a natural environment, with a glimpse of the yard in the background.

Cottage in Deerfield

4.97 out of 5 average rating, 182 reviews

Dreamy Guesthouse: sauna and private deck

You will feel like you're deep in the country while being close to everything on this 11-acre homestead, surrounded by woods. Featuring an infrared sauna, breezy porch, and firepit, this private guesthouse (next to our residence) is a 15-min walk to Deerfield Academy, Bement, Eaglebrook, and Historic Deerfield; a short drive to all five colleges; and less than three miles from award-winning Treehouse Brewery. Halfway between Brattleboro and Northampton, this is the perfect valley spot.

Guest favorite

A private deck area features colorful flower beds and potted plants. A large hanging chair is visible alongside patio seating, with a wooden deck leading toward the entrance. Sunshine filters in, highlighting the inviting outdoor space.

Apartment in Whately

4.94 out of 5 average rating, 218 reviews

Cozy, Private, Central 1 Bdrm, Large Yard

Half of an adorable bungalow in beautiful, private, picturesque setting. Minutes to 91, Northampton, Amherst, 5 colleges, Treehouse Brewery, Butterfly Conservatory, Historic Deerfield, Mohawk Trail… Oversized sunny bedroom with queen bed, pull-out double sofa. Living room has large sectional sofa, t.v. Full kitchen, with common appliances and cookware. Bathroom with shower/tub. Vaulted ceilings throughout. Slider to private deck and large yard, all separated from owners side of house

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, 186 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

A well-maintained stone walkway leads to a private entrance, flanked by a wooden railing and a vibrant flower bed featuring red and yellow tulips. A white picket fence adds charm, while a BBQ grill is positioned nearby on a paved area.

Apartment in Greenfield

4.96 out of 5 average rating, 436 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Small, cozy private Apt is located in West Greenfield in a quiet, safe neighborhood. Guests have own private driveway and entrance. There are 2 TV’s, one in living room & bedroom. High speed internet. Queen size bed & desk. Apt. Is 2 min's to Rt. 2, Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes

Top guest favorite

A living area features warm wooden paneling, hardwood floors, and natural light illuminating the space. A comfortable gray sofa is positioned on a colorful area rug, with a brick fireplace as a focal point. A wooden table and chair are present for workspace or dining.

Guesthouse in Amherst

4.96 out of 5 average rating, 636 reviews

Cozy get-away!

This quiet option is less than two miles from the center of downtown Amherst, a thriving college town with museums, libraries, small stores, restaurants for every budget, hiking trails galore. We offer a relaxing, TV-free space in a friendly, safe, residential neighborhood. Five minute walk to 2 bus stops. If you are looking for some privacy with access to western Mass., you've found it!

Top guest favorite

The living room features a comfortable sectional sofa and an armchair, paired with a round coffee table in the center. Large windows allow natural light to illuminate the space, complemented by indoor plants and light-colored walls.

Apartment in Greenfield

4.98 out of 5 average rating, 198 reviews

Lovely 2nd floor Apartment

This lovely spacious 1 bedroom apartment is situated on a quiet street in the heart of Greenfield. Only a 3 minute ride to a charming downtown & restaurants Enjoy lots of natural light and a calm office space with an additional futon for rest. Free parking on premises and access to nearby baseball field and tennis courts. A place you'll love to come back to.