Berkshire County Holiday Rentals

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Top Holiday Rentals Destinations in Berkshire County

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2149)
"Great place!"
United States
Nicole
The price is NZ$164
includes taxes & fees
29 Nov - 30 Nov
Vacation Village in the Berkshires

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very good, (986)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is NZ$289
includes taxes & fees
30 Nov - 1 Dec
Jiminy Peak Mountain Resort

Camping in Williamstown

1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is NZ$306
includes taxes & fees
14 Dec - 15 Dec
Huttopia Berkshires

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The price is NZ$243
includes taxes & fees
5 Dec - 6 Dec
The Ponds at Foxhollow

Holiday Home in Great Barrington

9.4 out of 10, Exceptional, (6)
The price is NZ$522
includes taxes & fees
30 Nov - 1 Dec
Pet Friendly Riverfront Home in Great Barrington

Holiday Home in Sherwood Forest

9.6 out of 10, Exceptional, (230)
"This property provides direct access to a lovely lake for kayaking and swimming. It is also a terrific location for Berkshire musts such as Jacob's Pillow and Tanglewood. The owner is quickly responsive to questions and directions for check in were easy to follow. The house has strong WiFi for any work days you have while traveling. Highly recommend and look forward to staying there again in the future! "
United States
Leslie K.
Peace and quiet on the lake

Villa in Lenox

10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox

Holiday Home in Great Barrington

10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Holiday Home in Hancock

9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is NZ$1,270
includes taxes & fees
29 Nov - 30 Nov
Comfortable Berkshires retreat on mtn resort, SISO

Holiday Home in Hancock

10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is NZ$1,836
includes taxes & fees
2 Dec - 3 Dec
Hancock Village Inn Near Jiminy Peak

Holiday Home in Pittsfield

9.8 out of 10, Exceptional, (149)
"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."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Holiday Home in Stockbridge

10.0 out of 10, Exceptional, (134)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Holiday Home in Lenox

9.2 out of 10, Wonderful, (32)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.

Holiday Home in Sheffield

9.8 out of 10, Exceptional, (93)
"The property was beautiful. Very spacious, inside and out. "
United States
Michelle C.
Antique Farmhouse Totally Restored

Holiday Home in Hancock

9.8 out of 10, Exceptional, (70)
"Great stay at a comfortable house with three generations of our family. Debbie was very responsive to several questions we had. The house was perfectly situated for day trips in the area. Thanks much!"
United States
Wayne G.
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Holiday Home in Florida

10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is NZ$767
includes taxes & fees
8 Dec - 9 Dec
The Greylock Cabin

Apartment in Dalton

2.0 star property
10.0 out of 10, Exceptional, (14)
"Easy check in, extremely well stocked kitchen, good wifi, and close to all the fun things to do in Western Mass! Extremely cute! Plenty of parking. We’d happily return. "
United States
Jacob S.
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Holiday Home in Florida

2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is NZ$594
includes taxes & fees
30 Nov - 1 Dec
Florida Mountain Log Cabin

Cottage in New Marlborough

9.6 out of 10, Exceptional, (17)
"Lovely cottage. Great for 2 couples. Lots of privacy for each but comfy gathering spots for dining and relaxing. Host was very responsive to questions. Great stay!"
United States
Lisa T.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Holiday Home in Stockbridge

10.0 out of 10, Exceptional, (103)
"Great house with gracious and responsive hosts. Everything in working order and the houseclean and grand."
United States
David H.
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 Berkshire County Hotel Reviews

Find out more about Berkshire County

Everything you need to know about Berkshire County 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 Berkshire County 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 Berkshire County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Berkshire County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Berkshire County. 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 Berkshire County 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 Berkshire County holiday rentals we have selected for you start as low as NZ$164 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Berkshire County rentals

At Expedia, we put the best Berkshire County 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 Berkshire County 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 Berkshire County 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 Berkshire County. 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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