The Berkshires holiday rentals

Search hundreds of travel sites at once for holiday home deals in The Berkshires

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Best The Berkshires holiday rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

R0 - R20 591R20 591 - R41 164R41 164 - R61 736R61 736 - R82 309R82 309+ per night

Property Types

ApartmentCottageHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in The Berkshires

Show all
Beautiful 1920's Colonial 20 Minutes from Tanglewood - Great Barrington
Beautiful 1920's Colonial 20 Minutes from Tanglewood
Great Barrington, MA, United States
Pet-friendly
Air conditioning
R4 691+
Check availability
Berkshire Mountain Cottage: in the Heart of the Berkshires - Great Barrington
Berkshire Mountain Cottage: in the Heart of the Berkshires
Great Barrington, MA, United States
Pet-friendly
Air conditioning
R5 271+
Check availability
Nestled minutes from Main Street, Great Barrington - Great Barrington
Nestled minutes from Main Street, Great Barrington
Great Barrington, MA, United States
Air conditioning
R5 306+
Check availability
Downtown GB apartment walk to shops and restaurants - Great Barrington
Downtown GB apartment walk to shops and restaurants
Great Barrington, MA, United States
Air conditioning
R5 552+
Check availability
Great Barrington apartment, Short walk to downtown - Great Barrington
Great Barrington apartment, Short walk to downtown
Great Barrington, MA, United States
Air conditioning
R6 009+
Check availability
Romantic Berkshires Cottage - Stunning Views, Pool - Great Barrington - Dining room
Romantic Berkshires Cottage - Stunning Views, Pool
Great Barrington, MA, United States
Free Wi-Fi
Pool
Pet-friendly
R6 167+
Check availability
Lakefront Berkshires Retreat with Deck, Dock and Boat! - Great Barrington - Bedroom
Lakefront Berkshires Retreat with Deck, Dock and Boat!
Great Barrington, MA, United States
7.2Good(20)
Free Wi-Fi
Pet-friendly
R9 101+
Check availability
Perfect Great Barrington Spot, Nature, and Views! - Great Barrington
Perfect Great Barrington Spot, Nature, and Views!
Great Barrington, MA, United States
Air conditioning
R9 736+
Check availability
Renovated house on the Hill. Walk everywhere! - Great Barrington
Renovated house on the Hill. Walk everywhere!
Great Barrington, MA, United States
Air conditioning
R9 926+
Check availability
Berkshire Vacation Rentals: Great Barrington Walkable To Lake And Town - Great Barrington - Dining room
Berkshire Vacation Rentals: Great Barrington Walkable To Lake And Town
Great Barrington, MA, United States
7.0Good(3)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R10 576+
Check availability
5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 ! - Great Barrington - Property amenity
5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 !
Great Barrington, MA, United States
9.7Wonderful(34)
Pool
Air conditioning
R11 279+
Check availability
Sunsets On Blue Hill, Newly Renovated Farmhouse - Great Barrington - Living room
Sunsets On Blue Hill, Newly Renovated Farmhouse
Great Barrington, MA, United States
Air conditioning
R12 333+
Check availability
A four-season forest cabin - Great Barrington - Living room
A four-season forest cabin
Great Barrington, MA, United States
R13 107+
Check availability
A great escape; secluded but close to all - contemporary home, mountain views - Great Barrington
A great escape; secluded but close to all - contemporary home, mountain views
Great Barrington, MA, United States
Air conditioning
R16 618+
Check availability
The Great Escape Ski Cottage W/Hot Tub @ Great Barrington - Great Barrington - Living room
The Great Escape Ski Cottage W/Hot Tub @ Great Barrington
Great Barrington, MA, United States
Free Wi-Fi
Air conditioning
R24 262+
Check availability
Moose Lodge by Avantstay Luxe Berkshires Escape - Great Barrington - Living room
Moose Lodge by Avantstay Luxe Berkshires Escape
Great Barrington, MA, United States
Free Wi-Fi
Air conditioning
R37 913+
Check availability
Useful Info

Good to know

Low season

June

High season

December

Average price (weeknight)

R113 675

Average price (weekend night)

R16 491
Cheapest month to stay with an average 86% drop in price.
Most expensive month to stay with an average 221% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

FAQs when booking a holiday home in The Berkshires

  • What types of holiday rentals are available in The Berkshires?

    There are loads of different property types that you can make your holiday home in The Berkshires. You’ll find apartments, cabins, campgrounds, cottages and houses.

  • Are there any pet-friendly holiday rentals in The Berkshires?

    There are a number of dog and pet-friendly The Berkshires holiday rentals, with around 17% allowing you to bring your pet along with you.

Where to stay in The Berkshires?

Our map will help you find the perfect place to stay in The Berkshires by showing you the exact location of each holiday home.

Everything you need to know for your stay in The Berkshires

Not what you’re looking for? Find thousands of other hotels, flights and car hire with KAYAK.