How much is a holiday rental in The Berkshires for tonight?

In the last 72 hours, users have found The Berkshires holiday rentals for tonight for as little as €133.

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 agritourism, apartments, cabins, caravan parks, chalets, condos, cottages, houses, lodges, villas and campgrounds.

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 20% allowing you to bring your pet along with you.

The Berkshires Holiday Rentals

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

...and more

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.

Best The Berkshires holiday rentals

Cozy Renovated with 1 parking space

Pittsfield, MA, United States

Air conditioning

€139+

Check availability

Berkshire Mountain Lodge

Pittsfield, MA, United States

8.5Very Good(658)

Parking

Free Wi-Fi

Pool

Air conditioning

€151+

Check availability

Cozy Great Barrington Home about 1 Mi to Ski Resort!

Great Barrington, MA, United States

9.8Wonderful(14)

Free Wi-Fi

Air conditioning

€406+

Check availability

Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9

Great Barrington, MA, United States

Parking

Free Wi-Fi

Pet friendly

Air conditioning

€340+

Check availability

Perfect for Winter Skiing!!

Pittsfield, MA, United States

Air conditioning

€666+

Check availability

The Great Escape Ski Cottage W/Hot Tub @ Great Barrington

Great Barrington, MA, United States

Free Wi-Fi

Air conditioning

€1,059+

Check availability

Sunsets On Blue Hill, Newly Renovated Farmhouse

Great Barrington, MA, United States

Air conditioning

€925+

Check availability

Berkshire Vacation Rentals: Great Barrington Cabin Sleeps 14 Walk To Town

Great Barrington, MA, United States

Parking

Free Wi-Fi

Pet friendly

Air conditioning

€758+

Check availability

Beautiful Lenox Home, 3 Mi to Shakespeare and Co!

Lenox, MA, United States

9.3Wonderful(20)

Free Wi-Fi

Air conditioning

€410+

Check availability

Renovated Downtown 1bedroom

Lenox, MA, United States

Air conditioning

€274+

Check availability

Pittsfield Home with Deck - 12 Mi to Jiminy Peak!

Pittsfield, MA, United States

9.0Wonderful(1)

Free Wi-Fi

€301+

Check availability

Historical Downtown 1bedroom

Lenox, MA, United States

Air conditioning

€277+

Check availability

A four-season forest cabin

Great Barrington, MA, United States

€655+

Check availability

Family-Friendly Richmond Cottage with Private Yard

Pittsfield, MA, United States

9.0Wonderful(1)

Free Wi-Fi

Pet friendly

Air conditioning

€521+

Check availability

Nestled minutes from Main Street, Great Barrington

Great Barrington, MA, United States

Air conditioning

€265+

Check availability

Downtown GB apartment walk to shops and restaurants

Great Barrington, MA, United States

Air conditioning

€277+

Check availability

Go to map

Low season	May
High season	December
Average price (weeknight)	€529
Average price (weekend night)	€222

Cheapest month to stay with an average 54% drop in price.

Most expensive month to stay with an average 495% rise in price.

Average Sun - Thu price over the last 2 weeks.

Average Fri & Sat price over the last 2 weeks.

How much is a holiday rental in The Berkshires for tonight?
In the last 72 hours, users have found The Berkshires holiday rentals for tonight for as little as €133. Search here for similar prices
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 agritourism, apartments, cabins, caravan parks, chalets, condos, cottages, houses, lodges, villas and campgrounds.
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 20% allowing you to bring your pet along with you.