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 Becket

4.93 out of 5 average rating, 169 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 • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • 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

Guest favorite

Cottage in Lanesborough

4.93 out of 5 average rating, 237 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.

Guest favorite

Cottage in Williamstown

4.89 out of 5 average rating, 179 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs .More than one dog 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!

Guest favorite

Cottage in Williamstown

4.99 out of 5 average rating, 105 reviews

Charming Williamstown Cottage

This beautifully restored small home in the heart of Williamstown is the perfect location for visitors to the attractions of the Berkshires. Walk to the theater, shopping, restaurants, Williams College campus and Sterling and Francine Clark Art Institute. A king master bedroom, 2 twins in the second upstairs bedroom, a full sized futon in the 3rd bedroom and a queen sleeper sofa provides sleep for 7-8 in total. All the amenities one might need for a comfortable stay are here for you!

Guest favorite

Cottage in Great Barrington

4.93 out of 5 average rating, 266 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.

Guest favorite

Cottage in Hinsdale

4.99 out of 5 average rating, 152 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 Sheffield, The Berkshires

4.92 out of 5 average rating, 131 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.

Guest favorite

Cottage in New Marlborough

4.95 out of 5 average rating, 118 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.

Guest favorite

Cottage in New Lebanon

4.95 out of 5 average rating, 185 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.

Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 267 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)

Guest favorite

Cottage in Monterey

5 out of 5 average rating, 45 reviews

Beaver Lodge

Come and enjoy total relaxation on 4 acres with a beaver pond, a meadow and forest. Feel like in a resort with a hammock, outdoor patio! All in the Berkshires, close to Tanglewood, Lake Garfield, Ski Butternut. The eco friendly house offers 3 bedrooms, the main on the first floor, one and a half bathrooms, a fully equipped kitchen, outdoor dining area, wood burning fireplace, electric car charger.

Guest favorite

Cottage in Lanesborough

4.93 out of 5 average rating, 142 reviews

The Sail Loft

Cozy, private house from 1850, located in the heart of the Berkshires. On a quiet street across from a pond, the cottage has access to the Ashuwillticook rail trail. Relax on the private back porch, or in the large bath tub. Sleep in late in the king sized bed, and then enjoy what the Berkshires has to offer. Close to several downhill and cross country ski spots, hiking trails and Tanglewood!