275+ Private Villas and Holiday Rentals in Great Barrington |
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Great Barrington Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Great Barrington

Discover more than 275 vacation rentals available in Great Barrington. 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 Great Barrington.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Great Barrington, 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 Great Barrington. On average, places to stay near Great Barrington offer 1354.15 ft², with nightly prices averaging US $583.

With Casai, finding and comparing holiday rentals in Great Barrington 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 Great Barrington

Type Count
Vacation Homes 196
Cottages 19
Holiday Apartments 17
Villas 1

Use these Quick Filters to Find a Holiday Rental in Great Barrington

★ 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 Great Barrington.

Weather in Great Barrington, MA

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

December - February
High 44°F       Low 20°F
March - May
High 68°F       Low 24°F
June - August
High 83°F       Low 57°F
September - November
High 78°F       Low 30°F

Top Attractions Around Great Barrington, MA

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


Ski Butternut
Beartown State Forest
Housatonic River Walk
Lake Buel
Dry Hill
Lake Mansfield Park
Mahaiwe Performing Arts Center
Les Trois Emme Winery
W.E.B. Du Bois Boyhood Homesite
Art et Industrie
Tanglewood Music Center
Catamount Ski Area
Mohawk Mountain Ski Area
Norman Rockwell Museum
National Shrine of the Divine Mercy
Lee Prime Outlets
Bousquet Ski Area
Lime Rock Park
Olana State Historic Site

Other Places to Stay in Great Barrington, MA


W.E.B. Du Bois Boyhood Homesite 140 Properties
Lake Mansfield Park 139 Properties
Mahaiwe Performing Arts Center 137 Properties
Housatonic River Walk 134 Properties
Art et Industrie 115 Properties
Ski Butternut 110 Properties
Alford 102 Properties
Dry Hill 57 Properties
Beartown State Forest 54 Properties
North Egremont 31 Properties
Egremont 31 Properties
New Marlborough 27 Properties

Frequently Asked Questions About Great Barrington?

What are the top holiday rentals in Great Barrington?

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

How many holiday rentals have private pools in Great Barrington?

Discover a selection of holiday rentals with private pools near Great Barrington 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 Great Barrington are best for families?

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

How many Casai.nz holiday rentals are available in Great Barrington?

As of 2026, Casai boasts over 275 properties listed in the Great Barrington area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Great Barrington.


People Also Ask

There are 275 Great Barrington, MA Holiday Rentals

Recently Booked Holiday Rentals in Great Barrington