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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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)
"Quiet and peaceful"
United States
Michael S.
$505 nightly
The price is $564
Oct 23 - Oct 24
Total with taxes and fees
Cozy Cottage-Sunset On The Lake
A cabin with a wooden deck, a covered porch, and a gravel driveway.

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
$499 nightly
The price is $554
Oct 12 - Oct 13
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
An outdoor patio with a fire pit, a grill, and outdoor furniture.

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

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
$339 nightly
The price is $380
Oct 14 - Oct 15
Total with taxes and fees
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
A two-story house with a balcony, a chimney, and a window with a view.

4. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
$1,843 nightly
The price is $1,871
Nov 9 - Nov 10
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
A red building with a sign that reads 'WORLD'S BEST CHRISTMAS SHOP.'

5. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Charlemont
$499 nightly
The price is $558
Nov 8 - Nov 9
Total with taxes and fees
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
A house with a porch and a small shed in the background.

6. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
$520 nightly
The price is $588
Oct 27 - Oct 28
Total with taxes and fees
Waterfront Lake Cottage - Lake Access -Kayaks
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

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"It was fine. No breakfast that I saw"
Michael 1-night trip
Posted 11 hours ago
Best Western Plus Berkshire Hills Inn & Suites

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews
54
Accommodation
82 Cottages
Lowest Price
$380
Highest Price
$1,871

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between $380 and $1,871 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 82 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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