
Holiday rentals in Sunderland
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Top-rated holiday rentals in Sunderland
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Amherst *NEW - Campus Convenience & Social Privacy
Your family will be comfortable and entertained when stay at our place. Conveniently located in the 5 college area, yet situated where all your guests can gather in quiet privacy. Just minutes from UMass Amherst and Amherst College as well as centrally located to the Hadley, Northampton, Sunderland and Deerfield areas. With 4 bedrooms (2 King bedrooms),an additional pull out couch, 2.5 baths, open living room/kitchen, and a large back deck there is plenty of space for comfort and socializing!

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.

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.

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.

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, TV. 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

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.)

The Suprenant House
Cozy home in the 5 college area, close to downtown Amherst minutes from UMASS and Amherst College in a rural part of Town with endless scenic views. Free fast Wifi and parking. During your stay you can enjoy a fully stocked kitchen, laundry essentials, books, board games and other activities. Your hosts live directly next door to the property and available to help at any time. You will be staying next to a working farm, where there are trucks and machines working daily.

The Silo | Next to UMass & open farmland/ nature
The Silo is one of only about 100 purpose-built silo homes—designed and constructed as a house, not converted from a farm structure. Adjacent to UMass and one mile from Amherst Center, it borders open farmland with wide-open skies, distant mountain views, and spectacular sunsets that feel worlds away. Inside, curved walls and natural light connect you with the landscape. Your guest suite is completely private, with its own exterior entrance and no shared indoor spaces.

Sunny Studio Apartment
Private neighborhood. Sunny second floor studio apartment, private entrance. Cathedral ceilings, renovated full bathroom, huge south facing windows. King sized bed + twin daybed in large open studio. Includes full kitchen + private laundry area. Beautiful outdoor picnic table and cozy fire pit. Close to all 5 colleges and major hospitals. 5 minutes to Umass. Walk to Cushman Cafe. Enjoy all the Pioneer Valley has to offer! Longterm rental available upon request.

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.

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.

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.
Popular amenities for Sunderland holiday rentals
Stay near Sunderland's top sights
Other great holiday rentals in Sunderland

New, Tranquil Apartment w/views of Mt. Sugarloaf

Serene South Deerfield Retreat

Cozy Private Basement Studio Near Downtown

Treetop Haven

Montague Meadows - Space for the Whole Family

Amherst Treehouse

Luxury mid-century forest home, mins from downtown

Lakefront Oasis at Lake Wyola
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- Stratton Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Stratton Mountain Resort
- Butternut Ski Area and Tubing Center
- University of Connecticut
- Bousquet Mountain Ski Area
- Dcu Center
- Ski Sundown
- Mount Monadnock
- Clark University
- Naumkeag
- University of Massachusetts Amherst
- Massachusetts Museum of Contemporary Art
- Norman Rockwell Museum
- Mount Greylock
- Hancock Shaker Village
- Mount Holyoke College
- Connecticut Convention Center
- Naismith Memorial Basketball Hall Of Fame
- Berkshire Botanical Garden
- The Montague Bookmill





