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Featured Cottages in The Berkshires and around

Perfect Vacation Get Away - Historical New Marlborough
Exterior

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (55)
"Lovely place!"
The price is €229
includes taxes & fees
31 Jul - 1 Aug
Perfect Vacation Get Away - Historical New Marlborough
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Exterior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (39)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Exterior

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (4)
"A lovely cabin centrally located in the Berkshires! Had everything we needed for our stay, including air conditioning during a heat wave! "
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Charming historic cottage on scenic road to Mt. Greylock
Exterior

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (111)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
East Otis Vacation Rental w/ Private Deck & BBQ!
Exterior

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (9)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Lake Views & Dock Access - Pittsfield Cottage!
Exterior

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (3)
"We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood."
Lake Views & Dock Access - Pittsfield Cottage!
Private Island - Largest Fresh Water Reservoir in Mass....
Outdoor dining

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....
Beachwood Cottage
Exterior

Beachwood Cottage

10.0 out of 10, Exceptional, (4)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage
Quiet rustic cottage with shared lake access
Exterior

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (109)
"Lovely lake house at the end of a long private road, perfect for a quiet getaway, close to all kinds of hiking and other natural attractions. Our hosts were super friendly and responsive. Highly recommended."
Quiet rustic cottage with shared lake access
Grandparent’s Cottage 250 steps to the lake
Sun-loungers, beach towels

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (7)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is €360
includes taxes & fees
3 Aug - 4 Aug
The Blue Elm - A Historic Berkshire Cottage
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Exterior

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.2 out of 10, Wonderful, (11)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Outdoor dining

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Cozy Becket Cottage Escape w/ Lake Access!
Cottage (2 Bedrooms) | Interior

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Outdoor dining

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

10.0 out of 10, Exceptional, (3)
"House was great. Great location. Clean and comfortable. No hair dryer like the listed stated. Host was quick to respond. Will stay again."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Outdoor dining

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

10.0 out of 10, Exceptional, (3)
"Stayed for 3 nights over Presidents Day weekend, and we loved the spot! Recently refreshed with a new kitchen, floors and fixtures, it’s still felt warm and inviting. The electric fire / heater in the living room was well used, and we cooked our meals with the new appliances and well equipped kitchen. Proximity to Great Barrington, Stockbridge, Lenox, Lee, and all of the outdoor adventures (and shopping/restaurants) worked out perfectly, even given the snowy/ice weather. Plenty of space for the...
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Modern Home Overlooking Mt. Greylock, Williamstown!
Terrace/patio

Modern Home Overlooking Mt. Greylock, Williamstown!

Modern Home Overlooking Mt. Greylock, Williamstown!
Cozy Berkshire cottage with fireplace.
Exterior

Cozy Berkshire cottage with fireplace.

9.8 out of 10, Exceptional, (25)
"House and property were beautiful, well stocked and perfectly situated close to everything but also quiet and scenic. Owner was fantastic to deal with. She was helpful and accommodating, even had a sweet card and little gift to welcome us. Would definitely stay here again!! "
Cozy Berkshire cottage with fireplace.
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Outdoor dining

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck
Waterfront Cottage 10 Min From Great Barrington
Terrace/patio

Waterfront Cottage 10 Min From Great Barrington

10.0 out of 10, Exceptional, (97)
"very comfortable, great location on the lake, and near good hiking and nice towns"
Waterfront Cottage 10 Min From Great Barrington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top The Berkshires Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Very nice"
David 1-night trip
Posted 22 hours ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between €229 and €360 per night. Whatever your budget, you'll find an ideal place to get in touch with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in The Berkshires?
Explore our 95 cottages in The Berkshires and then select your favourite. Whether you're organising a holiday with the whole fam or a break with pals, your perfect stay is just a few clicks away with Expedia.
Why book your cottage in The Berkshires with Expedia?
Booking a cottage in The Berkshires is as easy as clicking on your travel dates and choosing an ideal place for outdoor fun and relaxation. From upmarket retreats to affordable stays and cottages that include perks like a hot tub, Expedia has something for all styles and tastes. As for the best deals around? We've got them too!