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Search The Berkshires Cottage Rentals from CA $574

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for The Berkshires cottages

A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

1. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (54 reviews)
"Great lake house in the beautiful Berkshires. House looked just like the online pics. Kitchen fully stocked with everything you would need. Lake view & backyard were amazing! Lots of fun using kayaks & canoes."
United States
Rose Angela M.
The price is CA $335
CA $788 total
includes taxes & fees
Oct 23 - Oct 24
Cozy Cottage-Sunset On The Lake
An outdoor patio with a fire pit, a grill, and outdoor furniture.

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

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is CA $314
CA $584 total
includes taxes & fees
Oct 22 - Oct 23
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
A cabin with a wooden deck, a covered porch, and a gravel driveway.

3. 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 CA $319
CA $790 total
includes taxes & fees
Oct 5 - Oct 6
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A house with a porch and a small shed in the background.

4. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
The price is CA $449
CA $835 total
includes taxes & fees
Oct 27 - Oct 28
Waterfront Lake Cottage - Lake Access -Kayaks
A two-story house with a balcony, a chimney, and a window with a view.

5. 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 CA $1,288
CA $2,765 total
includes taxes & fees
Oct 7 - Oct 8
Berkshires farm, 30+ guests, 50 acres
A house with a deck, surrounded by trees and a grassy slope.

6. 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 CA $208
CA $574 total
includes taxes & fees
Oct 5 - Oct 6
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A wooden deck leading to a house with a view of a road and greenery.

7. Spacious Vermont Farmhouse 3 Mi to Mount Snow

Spacious Vermont Farmhouse 3 Mi to Mount Snow
3.0 star property
West Dover
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

Hotel On North

Hotel On North

8/10 Good
"Floors creak as it's an old hotel but the room and bathroom were really spacious. The town is meh bur the hotel was nice."
Robin 2-night trip
Posted 4 hours ago
Hotel On North

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews
55
Accommodation
84 Cottages
Lowest Price
CA $574
Highest Price
CA $2,765

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between CA $574 and CA $2,765 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 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.
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 Center, 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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