Photo by Photo courtesy of Berkshire Visitors Bureau

The Berkshires Vacation Rentals

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Vacation Rentals in The Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2147)
"Great place!"
United States
Nicole
$94 nightly
The price is $105
Nov 24 - Nov 25
Total with taxes and fees
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
Hancock
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
$149 nightly
The price is $166
Nov 24 - Nov 25
Total with taxes and fees
Jiminy Peak Mountain Resort

Huttopia Berkshires

1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
$170 nightly
The price is $190
Dec 14 - Dec 15
Total with taxes and fees
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
Lenox
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
$127 nightly
The price is $142
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.2 out of 10, Wonderful, (5)
$253 nightly
The price is $283
Nov 24 - Nov 25
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington

Peace and quiet on the lake

Sherwood Forest
9.6 out of 10, Exceptional, (228)
"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

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

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

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$1,026 nightly
The price is $1,111
Dec 2 - Dec 3
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak

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

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!

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
10.0 out of 10, Exceptional, (133)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
$722 nightly
The price is $733
Nov 24 - Nov 25
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO

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

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

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

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington
10.0 out of 10, Exceptional, (53)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Hancock
9.6 out of 10, Exceptional, (30)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
$705 nightly
The price is $787
Dec 24 - Dec 25
Total with taxes and fees
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Antique Farmhouse Totally Restored

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

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

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

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

Great Barrington
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!"
United States
Roberta
$1,189 nightly
The price is $1,328
Dec 1 - Dec 2
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

The Greylock Cabin

Florida
10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveler
$402 nightly
The price is $434
Dec 15 - Dec 16
Total with taxes and fees
The Greylock Cabin

Private Island - Largest Fresh Water Reservoir in Mass

Otis
8.6 out of 10, Excellent, (9)
"We had a great time. The owner Bill was a great host."
United States
Drew D.
Private Island - Largest Fresh Water Reservoir in Mass
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the The Berkshires vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

The Berkshires vacation 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 low season months. For more hustle and bustle, you may prefer to visit The Berkshires in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $105 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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At Expedia, we put the best The Berkshires vacation 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 vacation.

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