The Berkshires holiday rentals

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Best The Berkshires holiday rentals

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(17)
House
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R6 420+
Check availability
Cozy Great Barrington Home about 1 Mi to Ski Resort! - Great Barrington - Building
Cozy Great Barrington Home about 1 Mi to Ski Resort!
Great Barrington, MA, United States
9.8Wonderful(19)
House
Free Wi-Fi
Air conditioning
R8 901+
Check availability
4 Mi to Great Barrington: Berkshires Retreat! - Great Barrington - Living room
4 Mi to Great Barrington: Berkshires Retreat!
Great Barrington, MA, United States
Cottage
Free Wi-Fi
Air conditioning
R5 565+
Check availability
Amazing 2-bedroom apartment sunny and quiet in Great Barrington - Great Barrington - Bedroom
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Great Barrington, MA, United States
9.3Wonderful(25)
Apartment
Free Wi-Fi
Air conditioning
R3 654+
Check availability
Restored 1881 Farm House - Lenox - Kitchen
Restored 1881 Farm House
Lenox, MA, United States
9.8Wonderful(22)
House
Free Wi-Fi
Pet-friendly
Air conditioning
R6 638+
Check availability
Walk to Dining: Downtown Lenox Guest House! - Lenox - Patio
Walk to Dining: Downtown Lenox Guest House!
Lenox, MA, United States
9.6Wonderful(15)
Cottage
Free Wi-Fi
Air conditioning
R6 336+
Check availability
Main Street Delight 1bedroom - Lenox - Living room
Main Street Delight 1bedroom
Lenox, MA, United States
9.9Wonderful(24)
Apartment
Air conditioning
R5 800+
Check availability
Farmhouse-Loft -48 Main Street, Lenox, Ma - Lenox - Living room
Farmhouse-Loft -48 Main Street, Lenox, Ma
Lenox, MA, United States
10Wonderful(12)
Apartment
Air conditioning
R11 482+
Check availability
Heart Of Lenox Walk To Town Cozy Cottage! - Lenox - Living room
Heart Of Lenox Walk To Town Cozy Cottage!
Lenox, MA, United States
10Wonderful(47)
House
Free Wi-Fi
Air conditioning
R7 627+
Check availability
Newly Renovated Three Bedroom Haus In Lenox With Modern Interior Design. - Lenox - Patio
Newly Renovated Three Bedroom Haus In Lenox With Modern Interior Design.
Lenox, MA, United States
10Wonderful(19)
House
Free Wi-Fi
Air conditioning
R9 488+
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Historical Downtown 1bedroom - Lenox - Kitchen
Historical Downtown 1bedroom
Lenox, MA, United States
9.5Wonderful(16)
Apartment
Air conditioning
R5 331+
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Chic Modern Farmhouse 1 mile to Downtown Lenox - Lenox - Living room
Chic Modern Farmhouse 1 mile to Downtown Lenox
Lenox, MA, United States
10Wonderful(11)
House
Free Wi-Fi
Air conditioning
R22 915+
Check availability
Heart of Lenox!! - renovated downtown apartment - Lenox - Kitchen
Heart of Lenox!! - renovated downtown apartment
Lenox, MA, United States
9.8Wonderful(25)
Apartment
Air conditioning
R11 248+
Check availability
Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA - Lenox - Dining room
Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA
Lenox, MA, United States
9.8Wonderful(28)
Cottage
Free Wi-Fi
Air conditioning
R7 174+
Check availability
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)
House
Free Wi-Fi
Pet-friendly
R10 259+
Check availability
Walk to Dining Downtown Lenox Guest House! - Lenox
Walk to Dining Downtown Lenox Guest House!
Lenox, MA, United States
9.6Wonderful(9)
House
Free Wi-Fi
Air conditioning
R6 102+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

May
September
R3 234
R4 558
Cheapest month to stay with an average 34% drop in price.
Most expensive month to stay with an average 47% 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 tonight?

    In the last 72 hours, users have found The Berkshires holiday rentals for tonight for as little as R6 383. 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 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 4% 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