
Holiday rentals in Sunderland
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Top-rated holiday rentals in Sunderland
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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

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.

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 local ski resort Berkshire East. There are many sights, country roads, trails to explore, along with many varied excellent 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.

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.

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.

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!

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.

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.

Quiet Forest Apartment—Light, Books, Washer/Dryer
Wake up among 100-year-old trees, then drive ten minutes into Amherst for museums or sushi. Or hike out the door toward wooded trails. The apartment sits with our house on 5 acres of mature forest. 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.)

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

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!

Charming & quiet, walk to colleges
Cozy one bedroom second floor apartment nestled in a quiet friendly neighborhood. Bathroom renovated Nov 2022. Original 1800s woodwork with modern touches perfectly balances old and new, a reflection of our historic town. A short walk to great restaurants, museums, cafes, farm to table bistros and local pubs.
Popular amenities for Sunderland holiday rentals
Other great holiday rentals in Sunderland

Luxury 3BR home in the forest, mins from downtown

Spacious, Sunny* Woodland Retreat

Wood Turtle Woods

Serene South Deerfield Retreat

Sunny Studio Apartment

Amherst Treehouse

The Walnut Apartment

Cabin Style Rustic Getaway, with mini-splits
Destinations to explore
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- Stratton Mountain
- Six Flags New England
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Mount Greylock Ski Club
- Bushnell Park
- Brimfield State Forest
- Norman Rockwell Museum
- Bigelow Hollow State Park
- Wintonbury Hills Golf Course
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Bright Nights at Forest Park
- Nashoba Valley Winery, Distillery, Brewery and Restaurant
- Bousquet Mountain Ski Area
- Talcott Mountain State Park
- Hartford Golf Club
- Mount Tom State Reservation
- Beartown State Forest
- Berkshire Botanical Garden
- The Shattuck Golf Club
- Hooper Golf Course




