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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for The Berkshires cottages

House (3 Bedrooms) | Interior

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 £328
includes taxes & fees
29 Jun - 30 Jun
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Exterior

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, (82 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 £285
includes taxes & fees
30 Jun - 1 Jul
Perfect for a peaceful get away in clean fresh Vermont air!
Terrace/patio

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is £270
includes taxes & fees
30 Jun - 1 Jul
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
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 £1,829
includes taxes & fees
8 Jul - 9 Jul
Berkshires farm, 30+ guests, 50 acres
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 £418
includes taxes & fees
28 Jun - 29 Jun
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
House (4 Bedrooms) | Interior

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 £493
includes taxes & fees
23 Jun - 24 Jun
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 Red Lion Inn

The Red Lion Inn

8/10 Good
"I did not stay in the main building but had a room in a separate building on the same block. I quite liked my room away from the inn. It was roomy, quiet, across the street from a church, easy walk to the cafe, and there was a bunny 🐰 eating grass outside each night. I think I will request such a room away from the hubbub when I return. The food at the Red Lion's Inn's 'Widow's' tavern was delicious. Just know the buildings are indeed OLD so if you are seeking great water pressure or modern vibe, this is not your place. Love the history of this place!"
Tina 5-night trip
Posted 1 hour ago
The Red Lion Inn

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews
83
Accommodation
94 Cottages
Lowest Price
£270
Highest Price
£1,829

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between £270 and £1,829 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 94 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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