Search Cottages in The Berkshires

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for The Berkshires cottages

Exterior

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is SAR 702
SAR 1,370 total
includes taxes & fees
31 May - 1 Jun
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (2 reviews)
"It was an excellent place to stay. Super comfy and quiet, falling asleep to the sound of the creek. Well equipped with everything you need. Good fast wifi. Excellent value for the money. Great place if you want to really get away from it all."
United States
Seva L.
The price is SAR 507
SAR 887 total
includes taxes & fees
26 May - 27 May
Brookside cottage near the mountains and outdoor recreation
House (3 Bedrooms) | Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is SAR 735
SAR 2,078 total
includes taxes & fees
29 May - 30 May
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is SAR 4,162
SAR 8,174 total
includes taxes & fees
9 Jun - 10 Jun
Berkshires farm, 30+ guests, 50 acres
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.
View all properties
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"I loved the use of space for local artists to display there art. Beautiful work. The hotel was very clean. Loved that you could get a coffee or water throughout the day. I wish that the pool was opened all day. Ample parking"
Carol 2-night trip
Posted 6 hours ago
Hotel Downstreet, an Ascend Collection Hotel

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between SAR 887 and SAR 8,174 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 87 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!
How can I find cheap cottages in The Berkshires?
The easiest way to compare cheap cottages in The Berkshires is with Expedia's user-friendly filter tool. Refine your search by budget, star rating and amenities to discover excellent rates with only a few clicks.