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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

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 3.793.956 ₫
10.467.421 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
House (3 Bedrooms) | Interior

2. 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 5.820.864 ₫
14.400.402 ₫ total
includes taxes & fees
21 Sept - 22 Sept
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
House (4 Bedrooms) | Interior

3. Spacious Vermont Farmhouse 3 Mi to Mount Snow

Spacious Vermont Farmhouse 3 Mi to Mount Snow
3.0 star property
West Dover
The price is 9.874.680 ₫
20.303.382 ₫ total
includes taxes & fees
20 Sept - 21 Sept
Spacious Vermont Farmhouse 3 Mi to Mount Snow
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"Extremely friendly and helpful staff. Only complaint is very low toilet and slow internet speed."
robert 21-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews
1
Accommodation
65 Cottages
Lowest Price
10.467.421 ₫
Highest Price
20.303.382 ₫

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between 10.467.421 ₫ and 20.303.382 ₫ 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 65 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.