Cottage vacation rentals in Pioneer Valley

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Top-rated cottage rentals in Pioneer Valley

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Top guest favorite

Cottage in Petersham

4.99 out of 5 average rating, 210 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

Superhost

Cottage in Shutesbury

4.92 out of 5 average rating, 229 reviews

Lake Wyola House Shutesbury Massachusetts

Bright, airy recently remodeled three Bedroom lakefront home on Lake Wyola. Most rooms have a Lake View. Beds and bedding are new, each bedroom has a ceiling fan. A super place to make awesome memories. Perfect for a family vacation or romantic getaway. (6 people, two cars max) Close to local colleges, Amherst, Northampton and many attractions. Comfortable and relaxing. Big Screen TVs in the living room and master bedroom. Cable and Wifi. Full kitchen, washer & dryer. Sorry no pets.

Guest favorite

Cottage in Bernardston

4.88 out of 5 average rating, 335 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

Our quite and comfy home is conveniently located less than 2 miles from I-91, but a 1/4 mile down a country road giving you lots of privacy. The cottage is less than a mile from Crump 'N Fox Golf; 2 miles from Northfield Mount Hermon; 10 minutes from Greenfield & Stoneleigh Burnham; 15 min to Brattleboro, Deerfield Academy, Bement & Eaglebrook; 20 min to UMass, Amherst & Northampton; 30 minutes to Keene NH & Shelburne Falls and 45 min to the Basketball Hall of fame in Springfield & Mt Snow VT.

Guest favorite

Cottage in Southwick

4.98 out of 5 average rating, 125 reviews

Lake View, Hot Tub, 4 Kayaks, Central AC, Fire Pit

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for 2 families. (4 adults w/4 kids or 6 adults) Minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Top guest favorite

Cottage in Hinsdale

4.99 out of 5 average rating, 160 reviews

Cozy Cottage in the Berkshires

Come and enjoy our "happy place" year round! Our cozy, neat as a pin cottage is located in the beautiful Berkshires with gorgeous Ashmere lake views, spectacular flower beds and beach/lake access. Summer, fall, winter or spring, the cottage welcomes you, complete with a gift basket and fresh flowers. Enjoy the view of the lake off the spacious deck or play games in the grassy yard complete with fire pit for roasting marshmallows. Waterfront is only a minute or two walking distance away.

Guest favorite

Cottage in Becket

4.9 out of 5 average rating, 112 reviews

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 231 reviews

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit (access via uneven steps) • Canoe & 2 kayaks • Smart TV & 4 Google smart speakers • 1 Gigabit Wi-Fi • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Top guest favorite

Cottage in Deerfield

4.97 out of 5 average rating, 181 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

Cottage in Vernon

4.97 out of 5 average rating, 117 reviews

Vintage Bolton Lake

Fall colors coming soon!! Enjoy vintage charm and the calming lake waters! Vintage is nestled on the shores of picturesque Middle Bolton Lake. Relax, unplug, and savor the good life of times past. The cottage has been tastefully updated and outfitted with period furnishings to allow for vacationing in comfort and style. As our guest, you will enjoy full use of the cottage, WiFi, property, propane grill, smokeless firepit, kayaks and much more. Come enjoy vintage lakefront lifestyle.

Superhost

Cottage in Orange

4.92 out of 5 average rating, 190 reviews

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.

Guest favorite

Cottage in Becket

4.95 out of 5 average rating, 288 reviews

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX(will consider pets.)(90 second walk through wooded path to lake)

Guest favorite

Cottage in Orange

4.93 out of 5 average rating, 270 reviews

The Fishing Cottage: A Sweetwater Stay

Located on the shore of Tully Pond, The Fishing Cottage is a designed vacation home with breathtaking views of Tully Mountain. This 4-season Cottage has real salvaged barn wood walls; up-cycled maple floors and one-of-a kind scratch built furniture and lighting fixtures. The deconstructed architecture leaves exposed the electrical conduit and copper plumbing pipes, making the cottage feel alive and organic.