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, (2074)
"Nice room clean and friendly staff"
The price is AU$174
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (981)
"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."
The price is AU$250
includes taxes & fees
30 Oct - 31 Oct
Jiminy Peak Mountain Resort
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect place for a relaxing getaway! We loved everything! "
The price is AU$595
includes taxes & fees
18 Oct - 19 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
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
The price is AU$492
includes taxes & fees
2 Nov - 3 Nov
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
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.
9.2 out of 10, Wonderful, (31)
"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."
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 AU$1,627
includes taxes & fees
21 Oct - 22 Oct
Hancock Village Inn at Jiminy Peak
Peace and quiet on the lake
9.6 out of 10, Exceptional, (226)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AU$753
includes taxes & fees
19 Oct - 20 Oct
Comfortable Berkshires retreat on mtn resort, SISO
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$1,110
includes taxes & fees
26 Oct - 27 Oct
Guesthouse Cabin vacation rentals in Berkshire County
Private Island - Largest Fresh Water Reservoir in Mass
8.6 out of 10, Excellent, (9)
"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, (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."
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
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
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
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 AU$2,187
includes taxes & fees
20 Oct - 21 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Tranquil Lakeside Escape in the Berkshires
10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
Tranquil Lakeside Escape in the Berkshires
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
10.0 out of 10, Exceptional, (55)
"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!
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!
Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape
6.0 out of 10, (2)
"The barn was a great spot for some quality time with friends. We picked some herbs and rotator from the garden and made an amazing toast. Would definitely stay here again."
Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape
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

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 favourite 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 depend 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 AU$174 per night. Entering your travel dates in the search wizard might find you 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.