Photo by Photo courtesy of Berkshire Visitors Bureau

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Our top choices for The Berkshires cottages

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 NZ$1,030
includes taxes & fees
28 Dec - 29 Dec
Wilmington Retreat Near Trails, Skiing & Festivals
2.0 star property
The price is NZ$605
includes taxes & fees
20 Jan - 21 Jan 2026
Pet-Friendly Hudson Escape w/ Hot Tub
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
The price is NZ$629
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
2.0 star property
The price is NZ$2,952
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

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews
4
Accommodation
84 Cottages
Lowest Price
NZ$605
Highest Price
NZ$2,952

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between NZ$605 and NZ$2,952 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.
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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