Photo by Photo courtesy of Berkshire Visitors Bureau

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Check prices for these dates

Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
In one month
16 Jan - 18 Jan
In two months
13 Feb - 15 Feb

Our top choices for The Berkshires cottages

Exterior
Pet-Friendly Hudson Escape w/ Hot Tub

Cottage in Stottville

Pet-Friendly Hudson Escape w/ Hot Tub
2.0 star property
The price is €297
includes taxes & fees
1 Jan - 2 Jan 2026
Pet-Friendly Hudson Escape w/ Hot Tub
House (3 Bedrooms) | Interior
Wilmington Retreat Near Trails, Skiing & Festivals

Cottage in Wilmington

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveller
The price is €625
includes taxes & fees
28 Dec - 29 Dec
Wilmington Retreat Near Trails, Skiing & Festivals
Exterior
Berkshires farm, 30+ guests, 50 acres

Cottage in New Lebanon

Berkshires farm, 30+ guests, 50 acres
2.0 star property
The price is €1,494
includes taxes & fees
12 Jan - 13 Jan 2026
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.
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Top The Berkshires Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Wonderful breakfast, amazing relaxing hot tub, Beautiful clean room, staff friendly very helpful. Will stay again !!"
Karen 1-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews
3
Accommodation
84 Cottages
Lowest Price
€297
Highest Price
€1,494

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between €297 and €1,494 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 84 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!
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.
What is there to do in The Berkshires near my cottage?
One of the most important travel accessories for your The Berkshires trip is a good itinerary! Tanglewood Music Centre, Shakespeare and Company and The Mount are among the most popular sights if you're on your way to Lenox. Williamstown is also home to terrific attractions, such as Chapin Library of Rare Books and Manuscripts. In the mood to explore more? Carve out some time for Hopkins Observatory and Williams College Museum of Art too.

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