The Berkshires Vacation Rentals

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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for The Berkshires vacation rentals

Exterior

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,231 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is ￥16,347
￥19,985 total
includes taxes & fees
Feb 9 - Feb 10
Vacation Village in the Berkshires
Daily to-go breakfast for a fee

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
The price is ￥29,715
￥33,192 total
includes taxes & fees
Mar 8 - Mar 9
Jiminy Peak Mountain Resort
Exterior

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, (10 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
The price is ￥21,539
￥43,377 total
includes taxes & fees
Feb 9 - Feb 10
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Outdoor dining

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.
The price is ￥18,866
￥41,721 total
includes taxes & fees
Feb 9 - Feb 10
New Studio In Town, By the Water
Exterior

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (8 reviews)
"Healthy food too!"
United States
GEORGINA
The price is ￥26,461
￥29,557 total
includes taxes & fees
Mar 8 - Mar 9
Huttopia Berkshires
Exterior

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, (1 review)
"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.
The price is ￥21,539
￥43,377 total
includes taxes & fees
Feb 9 - Feb 10
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Pool

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
10.0 out of 10, Exceptional, (23 reviews)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Pool

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (16 reviews)
"Nice Place"
United States
Tom C.
The price is ￥21,539
￥43,377 total
includes taxes & fees
Feb 10 - Feb 11
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is ￥27,199
￥44,781 total
includes taxes & fees
Feb 23 - Feb 24
Home in Great Barrington
Interior

UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (14 reviews)
"lovely place to stay"
United States
Nancy P.
The price is ￥25,328
￥59,376 total
includes taxes & fees
Feb 26 - Feb 27
UNIQUE - 1BR Country Condo @ Jiminy Peak
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.6 out of 10, Exceptional, (11 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.
The price is ￥18,866
￥43,155 total
includes taxes & fees
Mar 1 - Mar 2
2-Bdr Apt In Town, By the Water
Gift shop

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, (3 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is ￥21,539
￥43,377 total
includes taxes & fees
Feb 10 - Feb 11
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
TV

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.
The price is ￥28,889
￥53,628 total
includes taxes & fees
Feb 16 - Feb 17
Florida Mountain Log Cabin
Outdoor dining

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.
The price is ￥20,439
￥45,451 total
includes taxes & fees
Feb 18 - Feb 19
Downtown | Waterfront | Walk to Shops
Pool

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is ￥21,539
￥43,377 total
includes taxes & fees
Feb 9 - Feb 10
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Smart TV, books

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.8 out of 10, Exceptional, (11 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.
The price is ￥25,187
￥62,027 total
includes taxes & fees
Feb 11 - Feb 12
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Outdoor dining

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
7.4 out of 10, Good, (12 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.
The price is ￥21,539
￥53,387 total
includes taxes & fees
Feb 9 - Feb 10
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Living area

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (14 reviews)
"Clean property, easy check in, and the owner was super communicative. "
United States
Amanda W.
The price is ￥22,797
￥44,254 total
includes taxes & fees
Feb 9 - Feb 10
Penthouse Apartment on Park Street
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is ￥36,947
￥79,906 total
includes taxes & fees
Mar 4 - Mar 5
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior detail

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is ￥29,715
￥50,050 total
includes taxes & fees
Feb 17 - Feb 18
3-bedroom house in beautiful Berkshires, close to amenities!
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay."
Robin 1-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about The Berkshires

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