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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, 197 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.

Apr 10 – 17

G$71,680 GYD per night

Cottage in Petersham

4.99 out of 5 average rating, 151 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.

Sep 25 – Oct 2

G$30,070 GYD per night

Cottage in Bernardston

4.88 out of 5 average rating, 287 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.

Mar 24 – 31

G$24,319 GYD per night

Cottage in Lanesborough

4.93 out of 5 average rating, 220 reviews

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

Sep 12 – 19

G$37,820 GYD per night

Cottage in Kinderhook

4.98 out of 5 average rating, 173 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.

Oct 15 – 22

G$29,831 GYD per night

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!

Feb 11 – 18

G$33,967 GYD per night

Cottage in New Lebanon

4.94 out of 5 average rating, 176 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.

Dec 16 – 23

G$24,135 GYD per night

Cottage in Shaftsbury

4.99 out of 5 average rating, 600 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.

Mar 6 – 13

G$90,680 GYD per night

Cottage in Dover

4.95 out of 5 average rating, 216 reviews

Cozy summer cottage in the woods of southern VT

-The Ice Pond Camp, East Dover, VT. Small well equipped country cottage, surrounded by nature & quaint beauty. Enjoy the lovely Southern Vermont seasons as you relax, disconnect, recharge & spend your days living a slower pace - surrounded by authentic rural beauty. Close to Wilmington and West Dover, (home of Mount Snow) and towns such as Putney and Brattleboro. Just minutes away are scenic villages, green farms, brooks,ponds and lakes, walking trails & country roads.

May 30 – Jun 6

G$24,731 GYD per night

Cottage in Orange

4.94 out of 5 average rating, 132 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.

Dec 15 – 22

G$25,116 GYD per night

Cottage in Becket

4.95 out of 5 average rating, 130 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.

Nov 28 – Dec 5

G$63,739 GYD per night

Cottage in Becket

4.94 out of 5 average rating, 237 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)

Jan 26 – Feb 2

G$39,482 GYD per night

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, 236 reviews

Artist Cottage

Sep 7 – 14

G$55,342 GYD per night

Cottage in Woodstock

4.9 out of 5 average rating, 376 reviews

Famous Architect - Streamside Cottage w/ hot tub

Sep 27 – Oct 4

G$38,988 GYD per night

Cottage in Phoenicia

4.89 out of 5 average rating, 802 reviews

Romantic hot tub cottage. Hiking/breweries nearby.

Aug 22 – 29

G$37,804 GYD per night

Cottage in Narragansett

5.0 out of 5 average rating, 189 reviews

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

Feb 2 – 9

G$41,948 GYD per night

Cottage in Ledyard

4.9 out of 5 average rating, 145 reviews

Waterfront cottage overhanging the water!

Dec 22 – 29

G$60,822 GYD per night

Cottage in Litchfield

4.89 out of 5 average rating, 259 reviews

Litchfield - Hot Tub - Mohawk Mountain - Fireplace

Sep 12 – 19

G$74,087 GYD per night

Cottage in Red Hook

4.92 out of 5 average rating, 324 reviews

Goose Landing Cottage by the lake with NEW Hot Tub

Dec 18 – 25

G$49,292 GYD per night

Cottage in Kerhonkson

4.84 out of 5 average rating, 141 reviews

Gunks Cottage|Fire Pit|Pool|Near Minnewaska Park

Dec 8 – 15

G$46,972 GYD per night

Pet-friendly cottage rentals

Cottage in Florida

4.82 out of 5 average rating, 102 reviews

Peaceful Mountain Cabin by Ski, Kayak, Museums +!

Dec 11 – 18

G$30,913 GYD per night

Cottage in North Bennington

4.9 out of 5 average rating, 291 reviews

Romantic Private Vermont Cottage - Waterfront

Jul 24 – 31

G$39,598 GYD per night

Cottage in Craryville

4.91 out of 5 average rating, 482 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Oct 30 – Nov 6

G$25,836 GYD per night

Cottage in Gilboa

4.94 out of 5 average rating, 201 reviews

Home Alone Mountain Retreat

Nov 6 – 13

G$33,042 GYD per night

Cottage in Red Hook

4.98 out of 5 average rating, 599 reviews

bright serene + spacious barn

Sep 24 – Oct 1

G$78,659 GYD per night

Cottage in Catskill

4.96 out of 5 average rating, 233 reviews

1930's Cottage charm air conditioned near hiking

Sep 23 – 30

G$20,556 GYD per night

Cottage in Argyle

4.99 out of 5 average rating, 115 reviews

Three Pines Lake House on Cossayuna Lake

May 12 – 17

G$49,223 GYD per night

Cottage in Claverack

4.98 out of 5 average rating, 244 reviews

‘Clavashack’ Country Cottage

Aug 18 – 23

G$40,940 GYD per night

Private cottage rentals

Cottage in Highland

4.91 out of 5 average rating, 538 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

Sep 15 – 22

G$32,585 GYD per night

Cottage in Newfane

4.89 out of 5 average rating, 216 reviews

Ridgeview: Cozy Cottage with a View

Apr 15 – 22

G$29,369 GYD per night

Cottage in West Stockbridge

4.98 out of 5 average rating, 107 reviews

Historic 1810 Farmhouse - Fully Renovated

May 31 – Jun 7

G$41,685 GYD per night

Cottage in Saugerties

4.93 out of 5 average rating, 217 reviews

New:Cozy Barn-Style Retreat Minutes From Woodstock

Oct 2 – 9

G$64,235 GYD per night

Cottage in Sturbridge

4.93 out of 5 average rating, 122 reviews

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

Jun 5 – 12

G$52,541 GYD per night

Cottage in Shaftsbury

4.96 out of 5 average rating, 112 reviews

Rollin Cottage

Oct 16 – 23

G$29,250 GYD per night

Cottage in Chichester

4.99 out of 5 average rating, 514 reviews

Garden Cottage In The Catskills

Sep 25 – Oct 2

G$25,711 GYD per night

Cottage in Hinsdale

4.99 out of 5 average rating, 141 reviews

Cozy Cottage in the Berkshires

Sep 24 – Oct 1

G$53,850 GYD per night

Destinations to explore