Cottage vacation rentals in Berkshire County

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Top-rated cottage rentals in Berkshire County

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Guest favorite

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 5 – 12

G$37,862 GYD per night

Guest favorite

Cottage in Great Barrington

4.93 out of 5 average rating, 235 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Oct 20 – 27

G$53,654 GYD per night

Guest favorite

Cottage in Sheffield, The Berkshires

4.93 out of 5 average rating, 103 reviews

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Nov 15 – 22

G$53,879 GYD per night

Guest favorite

Cottage in Hinsdale

4.99 out of 5 average rating, 141 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.

Apr 19 – 26

G$53,864 GYD per night

Guest favorite

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!

Jul 20 – 27

G$37,379 GYD per night

Superhost

Cottage in Canaan

4.9 out of 5 average rating, 126 reviews

Plan your Berkshires by the lake

Very comfortable three-bedroom cottage in a quiet, private association on Queechy Lake. There is also a pullout queen size couch. Perfect for families. Hi-speed Spectrum internet, AllClad cookware, electric range, microwave, sharp knives, coffee maker, charcoal BBQ, and tons of places to hike. Apple TV and a Bose Bluetooth soundbar. There is also a large Solo Stove firepit as well as 2 kayaks and a paddle board for tooling around the lake. Close to supermarkets. 15 minutes to Tanglewood!

Sep 9 – 16

G$54,842 GYD per night

Superhost

Cottage in Florida

4.82 out of 5 average rating, 101 reviews

Peaceful Mountain Cabin by Ski, Kayak, Museums +!

ENJOY A MOUNTAIN ADVENTURE You will fall in love with this magic cottage nestled within 2 acres of old growth forest. Breathe in the fresh air enjoying the mountain vistas and sipping some hot cocoa. Warm up by the pellet stove or gaze at the stars seating by the fire pit. Berkshire East Ski is a few min away as well as the famous hairpin turn and many national forests. MASS MoCA only 15 min away, and Mt. Greylock is nearby as well as many outdoor adventures, restaurants & pubs.

Nov 12 – 19

G$29,480 GYD per night

Guest favorite

Cottage in New Lebanon

4.94 out of 5 average rating, 175 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.

Oct 31 – Nov 7

G$24,141 GYD per night

Guest favorite

Cottage in New Marlborough

4.96 out of 5 average rating, 104 reviews

Converted Berkshire schoolhouse on a quiet river

Renovated schoolhouse on a quiet river in the Berkshires. This is the perfect place to unwind. Great for families and friends to relax and reconnect. Take a walk to the waterfalls, play croquet on the lawn, gather dinner from our seasonal garden and enjoy 'smores around the fire pit. Very private and woodsy, but close to Butternut for skiing, Great Barrington for shopping and access to all the music and art the Berkshires has to offer. Home is stylish, comfortable and inviting.

Oct 19 – 26

G$49,047 GYD per night

Guest favorite

Cottage in Becket

4.95 out of 5 average rating, 128 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.

Aug 17 – 24

G$98,742 GYD per night

Guest favorite

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)

May 5 – 12

G$38,665 GYD per night

Superhost

Cottage in Pittsfield

4.9 out of 5 average rating, 69 reviews

Cottage Getaway - access all the Berkshires offer!

Looking for a cozy getaway in the beautiful Berkshires? Come relax in a newly updated cottage that feels remote, but is located in the heart of Berkshire County. With quick driving access to all the area has to offer – skiing, hiking, outdoor exploring, lakes & waterfalls, museums, farms, apple orchards, one-of-a-kind eateries, bars, cafés, shopping, dispensaries, and more – all nestled in the valley of the comforting Berkshire Hills!

Aug 14 – 21

G$35,127 GYD per night