The Berkshires Holiday Rentals

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Holiday Rentals in The Berkshires

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2028)
"Really nice place at a reasonable price"
The price is NZ$211
includes taxes & fees
20 Oct - 21 Oct
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (979)
"Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!"
The price is NZ$288
includes taxes & fees
19 Oct - 20 Oct
Jiminy Peak Mountain Resort

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is NZ$190
includes taxes & fees
1 Oct - 2 Oct
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (131)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Amore Estate - beautiful room with many places to explore and relax in.

9.0 out of 10, Wonderful, (28)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (14)
"Amazing Inn. Cozy and everything we needed. "
The price is NZ$1,925
includes taxes & fees
1 Oct - 2 Oct
Hancock Village Inn at Jiminy Peak

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is NZ$822
includes taxes & fees
30 Sept - 1 Oct
Comfortable Berkshires retreat on mtn resort, SISO

Peace and quiet on the lake

9.6 out of 10, Exceptional, (222)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is NZ$1,204
includes taxes & fees
30 Sept - 1 Oct
Guesthouse Cabin vacation rentals in Berkshire County

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (8)
"Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay."
Contemporary Berkshire Home with Views of Taconic Golf Course

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (148)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

2.0 star property
10.0 out of 10, Exceptional, (11)
"My husband and I and our little dog had an amazing stay in Dalton. The space was clean, perfectly decorated and comfortable! We only stayed a few days and wanted to stay so much longer! Coffee for the humans and frog toys and treats for Sully! Very convenient to all the Berkshires has to offer. Communication with the owner was prompt and always helpful!! Highly recommend and hope to return. "
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

9.8 out of 10, Exceptional, (69)
"Beautiful location, very spacious, comfortable and clean."
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (73)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

10.0 out of 10, Exceptional, (1)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
The price is NZ$1,796
includes taxes & fees
13 Oct - 14 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (102)
"The Taggart House was a wonderful place to gather with friends and family to celebrate my birthday. The house is beautiful; the rooms are large; kitchen is great; bugs kept us from hanging out in the backyard but the conservatory was light and bright and a perfect spot for cocktails. We loved the proximity to the town of Stockbridge and we would walk back and forth a couple times a day. We had a couple of small issues, and Caitlin was very responsive in answering my questions/concerns. All in...
A Grand property in Historic Stockbridge
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.
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Top The Berkshires Hotel Reviews

Find out more about The Berkshires

Find out more about The Berkshires

Everything you need to know about The Berkshires holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the The Berkshires holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect The Berkshires holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

The Berkshires holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in The Berkshires. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A The Berkshires holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of The Berkshires holiday rentals we have selected for you start as low as NZ$190 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on The Berkshires rentals

At Expedia, we put the best The Berkshires holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top The Berkshires rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream The Berkshires holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around The Berkshires. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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Explore a world of travel with Expedia