Photo by Photo courtesy of Berkshire Visitors Bureau

Search The Berkshires Villa Rentals from CA $264

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Nov 20 - Nov 22
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Jan 8 - Jan 10

Our top choices for The Berkshires villas

An outdoor patio with a fire pit, wicker furniture, and string lights.

1. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our 2 night stay, everything was clean and worked smoothly. The hot tub and couch were the favorites, also enjoyed the coffee maker very much. Would highly recommended staying here!"
United States
Ross O.
The price is CA $264
CA $494 total
includes taxes & fees
Nov 10 - Nov 11
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A modern two-story house with large windows and a balcony.

2. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (13 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is CA $706
CA $817 total
includes taxes & fees
Nov 10 - Nov 11
Cozy Valley View Post & Beam Villa!
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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Learn more about The Berkshires

Tucked in western Massachusetts, this region blends culture and nature with world-class museums and lush hiking trails. Catch a summer concert at Tanglewood, explore Norman Rockwell's art in Stockbridge, or ski the slopes at Jiminy Peak in nearby Hancock.

See all hotels in The Berkshires
A large white building with multiple chimneys, surrounded by lush gardens with various flowers.
Photo by Photo courtesy of Berkshire Visitors Bureau
Open Photo by Photo courtesy of Berkshire Visitors Bureau

Top reviews in The Berkshires

A large, two-story house with a well-maintained lawn and a fence.
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
Lee

10/10 Excellent

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.
Canada
Lise
Reviewed October 17, 2019
Devonfield Inn B&B

Frequently Asked Questions

How much do villas in The Berkshires cost?

Prices for villas in The Berkshires range between CA $264 and CA $706 per night. No matter your budget, you'll find someplace that suits your needs with Expedia. 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.

Why book your villa in The Berkshires with Expedia?

We think planning a vacation shouldn't be hard, so if you're on the lookout for villas at a competitive rate, Expedia has your back. Save those pennies and select an all-inclusive stay, or splurge on a high-end villa to spoil your nearest and dearest. Our handy filters make it simple to find a property in The Berkshires that you'll adore.

How can I find cheap villas in The Berkshires?

The simplest way to score cheap villas in The Berkshires is with Expedia's filter tool. Fine-tune your search results by amenities, budget and star rating to land awesome prices in just a few keystrokes.

What is there to do near my villa in The Berkshires?

You'll discover almost endless ways to spend your time in The Berkshires. If you're on your way to Lenox, don't miss Tanglewood Music Center, Shakespeare and Company and The Mount. Planning a getaway in Williamstown? Chapin Library of Rare Books and Manuscripts, Hopkins Observatory and Williams College Museum of Art are among the top attractions in this city.

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