Berkshire County Holiday Rentals

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Top Holiday Rentals Destinations in Berkshire County

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2000)
"All around loved everything about the place! "
The price is AU$163
includes taxes & fees
21 Sept - 22 Sept
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (974)
"Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!"
The price is AU$268
includes taxes & fees
17 Sept - 18 Sept
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 AU$165
includes taxes & fees
17 Sept - 18 Sept
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (128)
"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

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Amazing Inn. Cozy and everything we needed. "
The price is AU$1,698
includes taxes & fees
17 Sept - 18 Sept
Hancock Village Inn at Jiminy Peak

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (222)
"Cabin was exactly what we were looking for in a weekend away. Great location, quiet, and had everything we needed. Hope to go back again soon! "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

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

9.0 out of 10, Wonderful, (27)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.

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

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

9.8 out of 10, Exceptional, (147)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

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 AU$1,062
includes taxes & fees
15 Sept - 16 Sept
Guesthouse Cabin vacation rentals in Berkshire County

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (7)
Contemporary Berkshire Home with Views of Taconic Golf Course

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
The price is AU$666
includes taxes & fees
15 Sept - 16 Sept
Florida Mountain Log Cabin!

Park Street Penthouse Apartment

9.6 out of 10, Exceptional, (11)
"The penthouse was beautiful and spacious. The Host Lea was very congenial and offered great suggestions for the location. I will definitely be coming back "
The price is AU$368
includes taxes & fees
14 Sept - 15 Sept
Park Street Penthouse Apartment

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!

2200sf 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."
2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (72)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town

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

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

The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly

10.0 out of 10, Exceptional, (1)
"Wonderful view, peaceful quiet area, cosy cabin."
The price is AU$693
includes taxes & fees
22 Sept - 23 Sept
The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly
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

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 favourite 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 depend 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 chosen for you start as low as AU$163 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.