The Berkshires Vacation Rentals
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Vacation Rentals in The Berkshires
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (857)
The price is ¥23,211
¥25,463 total
includes taxes & fees
May 14 - May 15
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (183)
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Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
Private Estate, Heated YEARROUND Outdoor Pool
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
Fox Hollow Luxury Ranch Laurel Lake
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (203)
Mountainside Condo Ski In Ski Out
Mountainside Condo Ski In Ski Out
8.8 out of 10, Excellent, (8)
The price is ¥23,211
¥29,051 total
includes taxes & fees
May 14 - May 15
Rockspring by AvantStay | Huge Berkshires Estate
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
Moose Lodge by AvantStay | Luxe Berkshires Escape
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (11)
Berkshire Lake access
Berkshire Lake access
10.0 out of 10, Exceptional, (41)
Stockbridge Home, Come Experience The Berkshires!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (11)
Peaceful, Post and Beam Loft, Sleeps 9
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (90)
Chic Pittsfield Home With A View!
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
The Winthrop Estate - 12K SF 32 Acres
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (2)
The price is ¥465,003
¥738,747 total
includes taxes & fees
Jun 13 - Jun 14
The Kemble- Built by a US Secretary of State in Lenox
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (15)
Perfect Vacation Get Away - Historical New Marlborough
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
The price is ¥23,367
¥42,154 total
includes taxes & fees
May 14 - May 15
Find your Sanctuary at The Rectory at Stockbridge
Find your Sanctuary at The Rectory at Stockbridge
10.0 out of 10, Exceptional, (1)
The price is ¥91,910
¥155,040 total
includes taxes & fees
May 14 - May 15
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other types of properties in The Berkshires you may be interested in
Life House Berkshires
Life House Berkshires
9.0 out of 10, Wonderful, (237)
The price is ¥15,422
¥17,226 total
includes taxes & fees
May 20 - May 21
The Red Lion Inn
The Red Lion Inn
8.8 out of 10, Excellent, (881)
The price is ¥18,622
¥24,282 total
includes taxes & fees
May 21 - May 22
Hotel Downstreet
Hotel Downstreet
8.6 out of 10, Excellent, (919)
The price is ¥23,211
¥25,926 total
includes taxes & fees
May 16 - May 17
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Search for holiday rentals in The Berkshires on Expedia! You can easily find your home rentals, villas, holiday apartments in The Berkshires using one of the methods below:
- View our selection of featured holiday rentals in The Berkshires
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Look no further and take a look at our great range of rental properties in The Berkshires!
Recent reviews of The Berkshires propertiesExpedia verified reviews
5/5 Excellent
"Excellent customer service at this property extremely clean. Very safe and very quiet family had a lot of fun with all the amenities "
A verified traveler stayed at Club Wyndham Bentley Brook
Posted 1 day ago
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