1632+ Rental Villas and Private Getaways in The Berkshires |
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The Berkshires Villa Rentals

About The Berkshires Vacation Rentals

There are more than 1632 incredible getaway rentals that are available in The Berkshires. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in The Berkshires.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in The Berkshires, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in The Berkshires. Places to stay near The Berkshires are 1055.66 ft² on average, with prices averaging CA $619 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in The Berkshires. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Private Villas, Resorts, and Rentals in The Berkshires

Type Count
Vacation Homes 860
Holiday Apartments 178
Cottages 76
Cabin Rentals 58
B&B 56
Others 26
Ski Chalet Rentals 12
Villas 12
Unique Vacation Rentals 2

Use these Quick Filters to Find a Vacation Rental in The Berkshires

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in The Berkshires with BedroomVillas.

Weather in The Berkshires, MA

View the weather forecast for The Berkshires before booking your The Berkshires Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near The Berkshires's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World The Berkshires's Research Top Attractions For Your Vacation


Jiminy Peak Mountain Resort
Tanglewood Music Center
Mass MoCA
Williams College
Ski Butternut
Norman Rockwell Museum
National Shrine of the Divine Mercy
Lee Prime Outlets
Bousquet Ski Area
Mount Greylock
Williamstown Theatre Festival
Cranwell Golf Club
Jacob's Pillow
Berkshire Museum
Hancock Shaker Village
Otis Ridge
Pittsfield State Forest
October Mountain State Forest
Beartown State Forest
Savoy Mountain State Forest

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Berkshire County 1,016 Properties
Hancock 146 Properties
Jiminy Peak Mountain Resort 146 Properties
Great Barrington 144 Properties
Lenox 100 Properties
Williamstown 83 Properties
Pittsfield 71 Properties
Lee 59 Properties
Becket 47 Properties
Stockbridge 43 Properties
North Adams 36 Properties
Monterey 35 Properties

Complexes around The Berkshires, MA


Wyndham Bentley Brook 34 Properties
Jiminy Peak 28 Properties
Ski 26 Properties
Berkshires 3 Properties
Courtyard 3 Properties
Econo Lodge Lee Great Barrington 3 Properties
Fairfield Inn 3 Properties
Fairfield Inn 3 Properties
Hampton Inn Suites 3 Properties
Hilton Garden Inn Pittsfield 3 Properties
Holiday Inn Club Vacations Oak N Spruce Resort 3 Properties
Holiday Inn Express Hotel Great Barrington Ihg 3 Properties
Howard Johnson 3 Properties
The Hill 3 Properties
The Williams Inn 3 Properties
See More Complexes

Frequently Asked Questions About The Berkshires?

What are the top hotels or resorts in The Berkshires?

We provide an array of great vacation destinations in The Berkshires. If you are looking to stay in or around the The Berkshires area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in The Berkshires:

How many vacation rentals have private pools in The Berkshires?

We have 121 luxury villas and vacation rentals featuriung a private pool in and near The Berkshires. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in The Berkshires is best for families?

Searching for a family-friendly getaway in The Berkshires? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in The Berkshires?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 1632 in the The Berkshires area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in The Berkshires. 

Nearby Neighborhood (1) 
Neighborhood Property Count
Sherwood Forest Rental Villas and Private Getaways in Massachusetts 69

People Also Ask

There are 128 hotels in The Berkshires 72 resorts, and 1108 rentals

Recently Booked Hotels, Resorts, or Rentals in The Berkshires