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Cottage vacation rentals in Western Massachusetts

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Top-rated cottage rentals in Western Massachusetts

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Cottage in Shutesbury

4.93 out of 5 average rating, 201 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 bed room 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 livingroom and master bedroom. Cable and Wifi. Full kitchen, washer & dryer. Sorry no pets.

Cottage in Petersham

4.99 out of 5 average rating, 153 reviews

Cider House Cottage

Antique guest cottage on a country 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.

Cottage in Bernardston

4.88 out of 5 average rating, 289 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.

Cottage in Highland

4.91 out of 5 average rating, 543 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

Cottage in Kinderhook

4.98 out of 5 average rating, 176 reviews

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

Cottage in Williamstown

4.9 out of 5 average rating, 165 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 full futon. Dog friendly for up to 2 dogs .More than two dogs will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

Cottage in Chichester

4.99 out of 5 average rating, 515 reviews

Garden Cottage In The Catskills

This quaint, relaxing cottage sits among Flowering Gardens in spring & summer, incredible Fall Foliage in autumn, & a Wonderland in Winter. Enjoy a peaceful cozy & private space with nature at your doorstep, an outdoor fire pit, stargazing, & your own stone patio at the edge of the woods. We love to share our garden, come pick your own! We are in the heart of The Catskill Mountains, 2 miles from the vibrant town of Phoenicia, in the hamlet of Chichester near the Stony Clove Creek

Cottage in New Lebanon

4.94 out of 5 average rating, 178 reviews

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.

Cottage in Shaftsbury

4.99 out of 5 average rating, 605 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

Cottage in Orange

4.94 out of 5 average rating, 133 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.

Cottage in Becket

4.96 out of 5 average rating, 134 reviews

Cozy lakeside cottage

Two-bedroom cottage on the lake with a dock nestled in the woodsy Sherwood Forest Community. Relax with the whole family at our quiet and peaceful oasis. You can swim, fish, kayak, and canoe in the water right from our private beach. Great place for a lakeside campfire at night. Our dock is perfectly situated for practicing yoga, meditation or quiet contemplation. Please note that accessing the house as well as getting down to the dock requires climbing stairs.

Cottage in Becket

4.94 out of 5 average rating, 239 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

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)

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Popular amenities for Western Massachusetts cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Great Barrington

4.93 out of 5 average rating, 239 reviews

Artist Cottage

Cottage in Ledyard

4.9 out of 5 average rating, 150 reviews

Waterfront cottage overhanging the water!

Cottage in Woodstock

4.9 out of 5 average rating, 377 reviews

Famous Architect - Streamside Cottage w/ hot tub

Cottage in Phoenicia

4.89 out of 5 average rating, 806 reviews

Romantic hot tub cottage. Hiking/breweries nearby.

Cottage in Litchfield

4.89 out of 5 average rating, 262 reviews

Litchfield - Hot Tub - Mohawk Mountain - Fireplace

Cottage in Narragansett

5.0 out of 5 average rating, 191 reviews

♥CozyGetaway-Narragansett-15min to Newport-HotTub♛

Cottage in Red Hook

4.92 out of 5 average rating, 325 reviews

Goose Landing Cottage by the lake with NEW Hot Tub

Cottage in West Hurley

4.94 out of 5 average rating, 251 reviews

Woodstock Carriage House HotTub FirePit Pool

Pet-friendly cottage rentals

Cottage in Florida

4.83 out of 5 average rating, 106 reviews

Peaceful Mountain Cabin by Ski, Kayak, Museums +!

Cottage in North Bennington

4.89 out of 5 average rating, 295 reviews

Romantic Private Vermont Cottage - Waterfront

Cottage in Gilboa

4.94 out of 5 average rating, 203 reviews

Home Alone Mountain Retreat

Cottage in Dover

4.95 out of 5 average rating, 216 reviews

Cozy summer cottage in the woods of southern VT

Cottage in Hillsdale

4.94 out of 5 average rating, 171 reviews

Cozy Cottage Catamount, Berkshires Walk to Brewery

Cottage in Red Hook

4.98 out of 5 average rating, 600 reviews

bright serene + spacious barn

Cottage in Craryville

4.91 out of 5 average rating, 483 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Cottage in High Falls

4.99 out of 5 average rating, 413 reviews

Sun Cottage- "A view with a room(s)."

Private cottage rentals

Cottage in Sturbridge

4.93 out of 5 average rating, 123 reviews

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

Cottage in Shaftsbury

4.96 out of 5 average rating, 113 reviews

Rollin Cottage

Cottage in Lanesborough

4.92 out of 5 average rating, 221 reviews

Stone School Cottage

Cottage in Newfane

4.89 out of 5 average rating, 216 reviews

Ridgeview: Cozy Cottage with a View

Cottage in Newbury

4.96 out of 5 average rating, 387 reviews

Tranquil Getaway-Dartmouth Lake Sunapee Region

Cottage in Guilford

4.92 out of 5 average rating, 134 reviews

Peaceful Cozy Cottage in the Vermont Woods

Cottage in Accord

4.88 out of 5 average rating, 218 reviews

Sweet Cottage on a Farm Road

Cottage in Woodstock

4.99 out of 5 average rating, 278 reviews

Grapevine Cottage

Destinations to explore