The Berkshires Vacation Rentals

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Our top choices for The Berkshires vacation rentals

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,301 reviews)
"Great place in Williamstown. Near ski resort."
United States
Jason
$126 nightly
The price is $141
Mar 22 - Mar 23
Total with taxes and fees
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
$149 nightly
The price is $166
Apr 1 - Apr 2
Total with taxes and fees
Jiminy Peak Mountain Resort

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
$147 nightly
The price is $165
Mar 23 - Mar 24
Total with taxes and fees
Huttopia Berkshires

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
$218 nightly
The price is $244
Mar 16 - Mar 17
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
United States
Antonio S.
$212 nightly
The price is $237
Mar 16 - Mar 17
Total with taxes and fees
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (12 reviews)
"Room was perfect location for skiing. Able to see slopes and a few of the chairlifts from room. Beds were super comfortable. Parking was close by and in private area which helped avoid parking in huge resort parking lot. Owner was very responsive."
United States
Charles
$218 nightly
The price is $244
Mar 16 - Mar 17
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
$256 nightly
The price is $288
Mar 14 - Mar 15
Total with taxes and fees
Downtown | Waterfront | Walk to Shops

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
$247 nightly
The price is $275
Mar 15 - Mar 16
Total with taxes and fees
Home in Great Barrington

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (24 reviews)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
$218 nightly
The price is $244
Mar 16 - Mar 17
Total with taxes and fees
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.6 out of 10, Exceptional, (12 reviews)
"Clean, close to town, very convenient. On a busy road, so just be aware of that. But overall a good place to stay. "
United States
Brian L.
$251 nightly
The price is $282
Mar 14 - Mar 15
Total with taxes and fees
2-Bdr Apt In Town, By the Water

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
$318 nightly
The price is $341
Mar 15 - Mar 16
Total with taxes and fees
Florida Mountain Log Cabin

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
$218 nightly
The price is $244
Mar 16 - Mar 17
Total with taxes and fees
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
$212 nightly
The price is $237
Mar 16 - Mar 17
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (34 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
$294 nightly
The price is $328
Mar 16 - Mar 17
Total with taxes and fees
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (10 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$239 nightly
The price is $269
Mar 14 - Mar 15
Total with taxes and fees
New Studio In Town, By the Water

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
$343 nightly
The price is $383
Mar 15 - Mar 16
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.8 out of 10, Exceptional, (21 reviews)
"We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip."
United States
Allison V.
$218 nightly
The price is $244
Mar 16 - Mar 17
Total with taxes and fees
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
9.8 out of 10, Exceptional, (17 reviews)
"lovely place to stay"
United States
Nancy P.
$421 nightly
The price is $470
Mar 15 - Mar 16
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
$306 nightly
The price is $342
Mar 23 - Mar 24
Total with taxes and fees
3-bedroom house in beautiful Berkshires, close to amenities!

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
7.6 out of 10, Good, (13 reviews)
"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "
United States
PK N.
$297 nightly
The price is $332
Apr 1 - Apr 2
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
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 $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on The Berkshires rentals

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.

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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