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

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Best The Berkshires holiday rentals

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Great Barrington, MA, United States

Air conditioning

€256+

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Downtown GB apartment walk to shops and restaurants

Great Barrington, MA, United States

Air conditioning

€268+

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Great Barrington apartment, Short walk to downtown

Great Barrington, MA, United States

Air conditioning

€290+

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Romantic Berkshires Cottage - Stunning Views, Pool

Great Barrington, MA, United States

Free Wi-Fi

Pool

Pet friendly

€308+

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Renovated Downtown 1bedroom

Lenox, MA, United States

Air conditioning

€376+

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Historical Downtown 1bedroom

Lenox, MA, United States

Air conditioning

€378+

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Beautiful Lenox Home, 3 Mi to Shakespeare and Co!

Lenox, MA, United States

9.3Wonderful(20)

Free Wi-Fi

Air conditioning

€400+

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Perfect Great Barrington Spot, Nature, and Views!

Great Barrington, MA, United States

Air conditioning

€471+

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Restored 1881 Farm House

Lenox, MA, United States

9.9Wonderful(13)

Free Wi-Fi

Pet friendly

Air conditioning

€479+

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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

€511+

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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

€560+

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5 Star Casual Elegance For 5 Star Guests

Lenox, MA, United States

Free Wi-Fi

Air conditioning

€569+

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Heart of Lenox!! - renovated downtown apartment

Lenox, MA, United States

Air conditioning

€577+

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Sunsets On Blue Hill, Newly Renovated Farmhouse

Great Barrington, MA, United States

Air conditioning

€596+

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A four-season forest cabin

Great Barrington, MA, United States

€633+

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

Great Barrington, MA, United States

Free Wi-Fi

Air conditioning

€1,173+

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Useful Info

Low season	September
High season	December
Average price (weeknight)	€981
Average price (weekend night)	€264

Cheapest month to stay with an average 59% drop in price.

Most expensive month to stay with an average 592% rise in price.

Average Sun - Thu price over the last 2 weeks.

Average Fri & Sat price over the last 2 weeks.

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.