The Berkshires holiday rentals

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Best The Berkshires holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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R0 - R20 779R20 779 - R41 540R41 540 - R62 300R62 300 - R83 061R83 061+ per night

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Most recommended holiday rentals in The Berkshires

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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 734+
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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 602+
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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
R5 851+
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Great Barrington apartment, Short walk to downtown - Great Barrington
Great Barrington apartment, Short walk to downtown
Great Barrington, MA, United States
Air conditioning
R6 063+
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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 006+
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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
R9 769+
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
R10 017+
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A Fun Farmhouse Near Ski Butternut - Great Barrington - Building
A Fun Farmhouse Near Ski Butternut
Great Barrington, MA, United States
Air conditioning
R10 549+
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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 382+
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A four-season forest cabin - Great Barrington - Living room
A four-season forest cabin
Great Barrington, MA, United States
R13 227+
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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 770+
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Berkshire Vacation Rentals: Great Barrington Cabin Sleeps 14 Walk To Town - Great Barrington - Living room
Berkshire Vacation Rentals: Great Barrington Cabin Sleeps 14 Walk To Town
Great Barrington, MA, United States
9.3Wonderful(15)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R18 119+
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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 502+
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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
R38 260+
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Charming 6 Bdrm Countryside Stay, Sauna and HotTub - Great Barrington - Living room
Charming 6 Bdrm Countryside Stay, Sauna and HotTub
Great Barrington, MA, United States
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R42 444+
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Charming Cabin On Scenic Road - Great Barrington - Bedroom
Charming Cabin On Scenic Road
Great Barrington, MA, United States
Pet-friendly
R83 061+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

June
December
R114 713
R16 642
Cheapest month to stay with an average 89% drop in price.
Most expensive month to stay with an average 405% 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 21% 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

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