Search The Berkshires Cottages

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3
In one month
Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Cottages in The Berkshires

Perfect Vacation Get Away - Historical New Marlborough
Enjoy al fresco dining and socializing in this serene outdoor patio area surrounded by lush greenery and trees.

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (55)
"2nd time here so I give it excellent review."
$256 nightly
The price is $281
Jul 31 - Aug 1
Total includes taxes and fees
Perfect Vacation Get Away - Historical New Marlborough
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Surrounded by tall trees, this cozy cabin offers a peaceful retreat in a natural setting.

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
Relax in the inviting porch area with Adirondack chairs and a cozy table.

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
Stroll through the serene garden, surrounded by vibrant flowers and lush greenery, with a charming house in the background.

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (110)
"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
Lake Views & Dock Access - Pittsfield Cottage!
Sit by the lake and enjoy a serene moment with a cup on the dock.

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....
Relax in this cabin's open-plan living area with a fireplace, scenic lake views, and comfortable seating.

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
Cozy interior with a brick fireplace, wooden ceiling, and a panelled wall.

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
Enjoy cooking in this well-equipped kitchen with a central island, dishwasher, stove, and refrigerator.

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
Enjoy outdoor dining or relaxation on the porch, surrounded by a serene lawn and mature trees.

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!! "
$369 nightly
The price is $412
Jul 16 - Jul 17
Total includes taxes and fees
The Blue Elm - A Historic Berkshire Cottage
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Relax in a peaceful room with large windows overlooking the surrounding trees, a perfect spot for socializing and taking in the views.

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!
Cozy cabin with a fireplace, dining area, and forest views.

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
Guests can enjoy an outdoor space with a table, chairs, and umbrella amidst lush greenery.

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
Enjoy cooking in this well-equipped kitchen with a microwave, stove, refrigerator, and coffee maker.

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

10.0 out of 10, Exceptional, (2)
"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!
Relax in a serene space with a seating area, large windows, and lush views.

Modern Home Overlooking Mt. Greylock, Williamstown!

Modern Home Overlooking Mt. Greylock, Williamstown!
Cozy Berkshire cottage with fireplace.
Enjoy meals in the kitchen with a stainless steel sink and black countertop, and dine at the round table with a mosaic top.

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
Enjoy cooking in this well-equipped kitchen with a large island, stainless steel appliances, and a window above the sink.

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
Enjoy the serene views from the cabin's spacious balcony with two lounge chairs.

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
Skiing & Hiking: Water-view Home in the Berkshires
House (3 Bedrooms) | Interior

Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between $281 and $412 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 91 cottages in The Berkshires and then select your favorite. Whether you're organizing a vacation 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!