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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for The Berkshires cottages

House (3 Bedrooms) | Interior

1. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is SAR 657
SAR 1,632 total
includes taxes & fees
11 Aug - 12 Aug
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Terrace/patio

2. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is SAR 822
SAR 1,526 total
includes taxes & fees
14 Aug - 15 Aug
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Exterior

3. Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
10.0 out of 10, Exceptional, (84 reviews)
"We had the most wonderful stay! The house and the property were beautiful, the amentities were excellent, and Linda Jane was an incredibly generous and accommodating host. We visit Bennington every year for Thanksgiving with family and we hope to rent with Linda Jane again in the future."
United States
Karissa A.
The price is SAR 713
SAR 1,531 total
includes taxes & fees
31 Aug - 1 Sep
Perfect for a peaceful get away in clean fresh Vermont air!
Exterior

4. 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 4,108
SAR 8,114 total
includes taxes & fees
8 Sep - 9 Sep
Berkshires farm, 30+ guests, 50 acres
House (4 Bedrooms) | Interior

5. Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
The price is SAR 969
SAR 2,860 total
includes taxes & fees
21 Aug - 22 Aug
Mtn-view Retreat in Huson Valley: Great for Groups
House (3 Bedrooms) | Interior

6. 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 841
SAR 2,081 total
includes taxes & fees
10 Aug - 11 Aug
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
House (4 Bedrooms) | Interior

7. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is SAR 1,427
SAR 2,454 total
includes taxes & fees
10 Aug - 11 Aug
3 Mi to Mount Snow: Spacious West Dover Home
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 Inn

The Yankee Inn

10/10 Excellent
"The staff were friendly, helpful with finding restaurants and other local attractions. Our room was immaculate and nicely furnished with modern furnishings in great condition. The room was quiet--we never heard our neighbors. It was pleasant to sit on the balcony and read. The location is great, 15 or 20 mins to Tanglewood depending on time. A very nice breakfast with lots of choices. We would definitely recommend this Inn to friends, and plan to return for future trips to Tanglewood and The Berkshires. ."
John 2-night trip
Posted 8 hours ago
The Yankee Inn

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between SAR 1,526 and SAR 8,114 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 90 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.