Vacation rentals in Sunderland

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Top-rated vacation rentals in Sunderland

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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
4.94 out of 5 average rating, 124 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 charming garden area is enclosed by a white picket fence, featuring an array of colorful flowers and tall sunflowers. The gray facade of the house provides a serene backdrop to the vibrant foliage, creating a welcoming atmosphere in the outdoor space.
Apartment in Conway
4.98 out of 5 average rating, 114 reviews

House Above the Hollow

A lovely peaceful spot set in the beautiful rolling hills of Conway Massachusetts, overlooking historic Pumpkin Hollow. In close proximity to Shelburne Falls, Deerfield, Greenfield, Amherst and Northampton along with the famed Tree House Brewery, just 10 min away. There are many sights, country roads, trails to explore, along with many varied restaurants to enjoy. "One of the most peaceful, scenic places I've ever stayed. You can really hear yourself think." Kathy Connolly Old Sabyrook CT.

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, 136 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.

Superhost
The exterior of a restored farmhouse is showcased, featuring a welcoming porch with pillars and multiple windows. The structure is surrounded by a grassy lawn, framed by trees in the background. A stone wall delineates the property, adding a natural element to the scene.
Home in Montague
4.94 out of 5 average rating, 194 reviews

Modern farmhouse close to Montague Retreat Center

This is a fully restored 1880 farmhouse five min. from Montague Retreat Center, 20 min. from Amherst and 25 min. to Northampton. Our house has modern amenities: radiant concrete floors, high end appliances/countertops, a steam shower and 7 ft, radiant heated copper bath tub. Lots of light, open spaces, cathedral ceilings and an outdoor playset for kids. The house is set on 3/4 of an acre with lots of beautiful gardens and is located near Montague Center, where there are restaurants and shops.

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 354 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!

Guest favorite
A spacious living area is highlighted by a curved sectional sofa facing a media console, featuring a variety of television options. Large windows invite natural light, while warm wooden beams add structural interest to the ceiling.
Home in Deerfield
4.81 out of 5 average rating, 253 reviews

Perfectly Polished Deerfield Home 5 min to I-91

A perfectly polished home, nestled in the Sugarloaf Mountain Range with a view of Mount Toby! This property offers 4 bedrooms and 4 beds. With over 2000 sqft of living space, you will enjoy coming home to wind down after a day at Yankee Candle, hiking, or other event in the beautiful Pioneer Valley. The house has something for everyone, whether it’s streaming your favorite show on Netflix, Hulu or Prime Video or relaxing on the patio deck while the kids enjoy the huge pool and water slide!

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, 116 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, 110 reviews

Forest Hideaway—Light, Privacy, Washer/Dryer

Wake up among 100-year-old trees, then drive ten 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 peaceful and practical, ideal for a weekend getaway or an extended stay, great 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 charming cabin with a rustic red exterior is nestled among the trees. It features a unique cobblestone chimney and multiple windows that allow natural light to flood the interior. A path leads to the entrance, surrounded by lush greenery.
Cabin in Shutesbury
4.99 out of 5 average rating, 106 reviews

Paradise Boathouse

Take a break and unwind at this peaceful oasis. The Paradise Boathouse is your hideout in the woods, nearby to Lake Wyola. Come to retreat and reset in this charming cabin with cobblestone chimney and mini- claw foot tub. This is a perfect place for writers and nature lovers. In winter enjoy the wood stove and a view of the lake below. Ice skating, ice fishing and x cross country skiing are right outside your door. And in summer swimming, boating and hiking!

Top guest favorite
A living room is displayed, featuring a comfortable blue couch adorned with patterned pillows. Three framed landscape images are mounted on the wall above a wooden coffee table. Natural light enters through a window with sheer curtains, illuminating a cozy reading nook in the background.
Apartment in Northampton
4.99 out of 5 average rating, 229 reviews

Cozy Haven: Convenience & Charm

Welcome to our charming Florence, Massachusetts Airbnb! Only 10 minutes from downtown Northampton, our newly renovated property blends comfort, convenience, and natural beauty. Our location provides swift access to Northampton's vibrant heart. Within a 10-minute drive, you'll be amid bustling streets with eclectic shops, superb dining, and a lively arts scene. Explore boutiques, galleries, and cafes that define Northampton's creative and entertaining spirit.

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, 481 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
Guesthouse in Amherst
4.96 out of 5 average rating, 683 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!

Popular amenities for Sunderland vacation rentals