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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R1 248 - R21 254R21 254 - R41 243R41 243 - R61 232R61 232 - R81 221R81 221+ per night

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Most recommended holiday rentals in The Berkshires

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Studio Loft in the Berkshires - Great Barrington - Living room
Studio Loft in the Berkshires
Great Barrington, MA, United States
10Wonderful(1)
Free Wi-Fi
Air conditioning
R2 340+
Check availability
Salisbury Cottage Retreat - Salisbury - Living room
Salisbury Cottage Retreat
Salisbury, CT, United States
9.8Wonderful(13)
Free Wi-Fi
Air conditioning
R4 629+
Check availability
Walk to the Outfield of Lime Rock Park - Salisbury - Living room
Walk to the Outfield of Lime Rock Park
Salisbury, CT, United States
9.1Wonderful(17)
Parking
Free Wi-Fi
Air conditioning
R5 201+
Check availability
Renovated Downtown 1bedroom - Lenox - Living room
Renovated Downtown 1bedroom
Lenox, MA, United States
10Wonderful(13)
Air conditioning
R5 236+
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Historical Downtown 1bedroom - Lenox - Kitchen
Historical Downtown 1bedroom
Lenox, MA, United States
9.5Wonderful(16)
Air conditioning
R5 236+
Check availability
Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9 - Great Barrington - Living room
Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9
Great Barrington, MA, United States
9.8Wonderful(16)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R5 669+
Check availability
Romantic Berkshires Cottage - Stunning Views, Pool - Great Barrington - Dining room
Romantic Berkshires Cottage - Stunning Views, Pool
Great Barrington, MA, United States
9.9Wonderful(29)
Free Wi-Fi
R6 016+
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Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining - Great Barrington - Patio
Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining
Great Barrington, MA, United States
9.4Wonderful(13)
Free Wi-Fi
Pet-friendly
Air conditioning
R7 212+
Check availability
Restored 1881 Farm House - Lenox - Kitchen
Restored 1881 Farm House
Lenox, MA, United States
9.8Wonderful(20)
Free Wi-Fi
Pet-friendly
Air conditioning
R7 957+
Check availability
Beautiful Lenox Home, 3 Mi to Shakespeare and Co! - Lenox - Living room
Beautiful Lenox Home, 3 Mi to Shakespeare and Co!
Lenox, MA, United States
9.1Wonderful(20)
Free Wi-Fi
Air conditioning
R8 044+
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Great Barrington Lakeside Getaway with Kayak and Grill - Great Barrington - Living room
Great Barrington Lakeside Getaway with Kayak and Grill
Great Barrington, MA, United States
8.8Very Good(8)
Free Wi-Fi
Air conditioning
R8 235+
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5 Star Casual Elegance For 5 Star Guests - Lenox - Patio
5 Star Casual Elegance For 5 Star Guests
Lenox, MA, United States
10Wonderful(38)
Free Wi-Fi
Air conditioning
R8 478+
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Country Living With A Lake View - Salisbury - Patio
Country Living With A Lake View
Salisbury, CT, United States
10Wonderful(3)
Air conditioning
R8 582+
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Heart of Lenox!! - renovated downtown apartment - Lenox - Kitchen
Heart of Lenox!! - renovated downtown apartment
Lenox, MA, United States
9.8Wonderful(23)
Air conditioning
R10 090+
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Lakefront Berkshires Retreat with Deck, Dock and Boat! - Great Barrington
Lakefront Berkshires Retreat with Deck, Dock and Boat!
Great Barrington, MA, United States
7.3Good(21)
Free Wi-Fi
Pet-friendly
R10 194+
Check availability
Berkshire Mountain Lakefront Log House Family Retreat - Salisbury - Living room
Berkshire Mountain Lakefront Log House Family Retreat
Salisbury, CT, United States
10Wonderful(2)
R15 707+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

May
April
R4 306
R5 431
Cheapest month to stay with an average 39% drop in price.
Most expensive month to stay with an average 41% 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

  • How much is a holiday rental in The Berkshires for this weekend?

    In the last 72 hours, users have found The Berkshires holiday rentals for this weekend for as little as R6 318 per night. 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, cottages, houses, villas, cabins, campgrounds and lodges.

  • 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 5% 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