1568+ Private Villas and Holiday Rentals in The Berkshires |
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The Berkshires Holiday Rentals

About Casai's Private Villas and Holiday Rentals in The Berkshires

Discover more than 1568 vacation rentals available in The Berkshires. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in The Berkshires.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in The Berkshires, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near The Berkshires. On average, places to stay near The Berkshires offer 1046.31 ft², with nightly prices averaging CA $617.

With Casai, finding and comparing holiday rentals in The Berkshires is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in The Berkshires

Type Count
Vacation Homes 823
Holiday Apartments 171
Cottages 72
Villas 12

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

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in The Berkshires.

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

Top Attractions Around The Berkshires, MA

Casai offers a large selection of top attractions around The Berkshires . Research things to do on your vacation before you visit The Berkshires.


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

Other Places to Stay in The Berkshires, MA


Berkshire County 1,148 Properties
Great Barrington 160 Properties
Hancock 157 Properties
Jiminy Peak Mountain Resort 157 Properties
Lenox 133 Properties
Williamstown 105 Properties
Pittsfield 88 Properties
Lee 70 Properties
Becket 49 Properties
Stockbridge 45 Properties
Monterey 39 Properties
Otis 38 Properties

Frequently Asked Questions About The Berkshires?

What are the top holiday rentals in The Berkshires?

With numerous options available in The Berkshires, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in The Berkshires:

How many holiday rentals have private pools in The Berkshires?

Discover a selection of holiday rentals with private pools near The Berkshires with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in The Berkshires are best for families?

If you're searching for a family-friendly holiday home in The Berkshires, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in The Berkshires:

How many Casai.ca holiday rentals are available in The Berkshires?

As of 2025, Casai boasts over 1568 properties listed in the The Berkshires area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in The Berkshires.

Nearby Neighborhood (1) 
Neighborhood Property Count
Sherwood Forest Vacation Rentals in Massachusetts 54

People Also Ask

There are 1568 The Berkshires, MA Holiday Rentals

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