Search The Berkshires Cottages

Start date: Check-in selected.
End date: Check-out
    bundle and save illustration

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
    one key illustration

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Cottages in The Berkshires

Our top choices for The Berkshires cottages

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....
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"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!! "
$362 nightly
The price is $404
Sep 2 - Sep 3
Total with taxes and fees
The Blue Elm - A Historic Berkshire Cottage
Perfect Vacation Get Away - Historical New Marlborough
Exterior

Perfect Vacation Get Away - Historical New Marlborough

9.2 out of 10, Wonderful, (57)
"Lovely place!"
$253 nightly
The price is $278
Oct 1 - Oct 2
Total with taxes and fees
Perfect Vacation Get Away - Historical New Marlborough
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)
"We were there for 2 nights for visiting day at a camp in the Berkshires. The home is very comfortable and clean. We enjoyed our stay! "
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
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, (114)
"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
Entire cottage in Berkshire Villiage
Exterior

Entire cottage in Berkshire Villiage

3.0 star property
9.8 out of 10, Exceptional, (6)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
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, (7)
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
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!

9.4 out of 10, Exceptional, (13)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Beachwood Cottage
Exterior

Beachwood Cottage

9.6 out of 10, Exceptional, (5)
"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
Luxury Vacation Rental in the Berkshires!
House (3 Bedrooms) | Interior

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Spacious Historic Home in the Berkshires!
House (5 Bedrooms) | Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
A-frame Cabin w/ Furnished Deck in Becket!
House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
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
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!
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, (6)
"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
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
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Terrace/patio

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From 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)
"Very nice house. Owners very helpful."
Cozy Berkshire cottage with fireplace.
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

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Room was very clean. There is a lot to do at the property, 2 pools, activities for the kids. Lots of things to do in the area "
Judy 2-night trip
Posted 4 days ago
Vacation Village in the Berkshires
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

10/10 Excellent
"Fantastic breakfast, perfect location, fun vibe, beautiful pool area, an environment that encourages conversation with other guests. Room was spacious but needed a nightstand on either side of the bed. "
Leigh 1-night trip
Posted 11 days ago
The Porches Inn at Mass MoCA

Find out more about The Berkshires

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews
Accommodation
97 Cottages
Lowest Price
$278
Highest Price
$404

Explore a world of travel with Expedia

Explore a world of travel with Expedia