The Berkshires Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for The Berkshires holiday rentals

Exterior

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,266 reviews)
"Excellent location and terrific space and amenities."
United States
Michelle
The price is HK$872
HK$1,060 total
includes taxes & fees
29 Mar - 30 Mar
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 HK$1,478
HK$1,651 total
includes taxes & fees
12 Mar - 13 Mar
Jiminy Peak Mountain Resort
Exterior

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (9 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$1,316
HK$1,470 total
includes taxes & fees
16 Mar - 17 Mar
Huttopia Berkshires
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 HK$2,033
HK$4,219 total
includes taxes & fees
24 Mar - 25 Mar
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is HK$3,128
HK$5,476 total
includes taxes & fees
2 Mar - 3 Mar
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

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.
The price is HK$821
HK$1,817 total
includes taxes & fees
2 Mar - 3 Mar
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (34 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$2,338
HK$5,083 total
includes taxes & fees
5 Mar - 6 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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, (13 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 HK$1,392
HK$3,267 total
includes taxes & fees
16 Mar - 17 Mar
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.0 out of 10, Wonderful, (11 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,496
HK$2,344 total
includes taxes & fees
12 Mar - 13 Mar
Family Ski Getaway in the Berkshires
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 HK$1,437
HK$2,667 total
includes taxes & fees
1 Mar - 2 Mar
Florida Mountain Log Cabin
TV, fireplace, printers

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

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"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
The price is HK$4,448
HK$10,418 total
includes taxes & fees
27 Feb - 28 Feb
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior

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.
The price is HK$1,752
HK$3,678 total
includes taxes & fees
1 Mar - 2 Mar
UNIQUE - 1BR Country Condo @ Jiminy Peak
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 HK$1,260
HK$2,106 total
includes taxes & fees
2 Mar - 3 Mar
Home in Great Barrington
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,853
HK$3,904 total
includes taxes & fees
23 Mar - 24 Mar
Cheerful 3-bedroom cottage with woodstove
Exterior detail

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is HK$1,407
HK$2,402 total
includes taxes & fees
2 Mar - 3 Mar
3-bedroom house in beautiful Berkshires, close to amenities!
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, (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.
The price is HK$938
HK$2,216 total
includes taxes & fees
28 Feb - 1 Mar
2-Bdr Apt In Town, By the Water
Pool

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.
The price is HK$1,235
HK$2,568 total
includes taxes & fees
2 Mar - 3 Mar
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,104
HK$3,809 total
includes taxes & fees
8 Mar - 9 Mar
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is HK$1,847
HK$3,183 total
includes taxes & fees
4 Mar - 5 Mar
The Greylock Cabin
Outdoor dining

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.
The price is HK$1,071
HK$2,655 total
includes taxes & fees
2 Mar - 3 Mar
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

The Williams Inn

The Williams Inn

10/10 Excellent
"nice aesthetics"
Zixuan 3-night trip
Posted 2 days ago
The Williams Inn

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