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The Berkshires Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in The Berkshires

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2141)
"Great place!"
United States
Nicole
The price is HK$576
HK$729 total
includes taxes & fees
23 Nov - 24 Nov
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

3.0 star property
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
The price is HK$1,160
HK$1,295 total
includes taxes & fees
23 Nov - 24 Nov
Jiminy Peak Mountain Resort
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
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
The price is HK$937
HK$1,047 total
includes taxes & fees
5 Dec - 6 Dec
The Ponds at Foxhollow
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Apartment in Hancock

10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in our fun, pirate themed suite. Which is really what caught our attention in making our reservation. It was so thoughtfully decorated, and suited the theme, while still being a comfortable place to enjoy being in. Everything was in wonderful condition, and had all the amenities we needed. Our host, Howie, was incredibly attentive, personable, and made sure we were taken care of. I was very disorganized, and he went out of his way to get me all the information we needed...
United States
Karen
The price is HK$817
HK$1,834 total
includes taxes & fees
24 Nov - 25 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Apartment in Hancock

10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is HK$817
HK$1,834 total
includes taxes & fees
23 Nov - 24 Nov
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Apartment in Hancock

10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is HK$817
HK$1,834 total
includes taxes & fees
24 Nov - 25 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

Condo in Hancock

10.0 out of 10, Exceptional, (14)
"Clean and quiet, nicely decorated! "
United States
Robert
The price is HK$1,004
HK$2,704 total
includes taxes & fees
23 Nov - 24 Nov
UNIQUE - 1BR Country Condo @ Jiminy Peak
Exterior
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Apartment in Hancock

9.4 out of 10, Exceptional, (16)
"Nice Place"
United States
Tom C.
The price is HK$817
HK$1,834 total
includes taxes & fees
24 Nov - 25 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Indoor pool
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Apartment in Hancock

10.0 out of 10, Exceptional, (3)
"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 HK$817
HK$1,835 total
includes taxes & fees
23 Nov - 24 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Exterior
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Apartment in Hancock

9.6 out of 10, Exceptional, (30)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is HK$1,230
HK$2,530 total
includes taxes & fees
23 Nov - 24 Nov
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
1 bedroom, WiFi, bed sheets
Charming Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

9.4 out of 10, Exceptional, (39)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is HK$1,051
HK$1,581 total
includes taxes & fees
23 Nov - 24 Nov
Charming Apt in 18th c Berkshire Farmhouse
Outdoor dining
Downtown | Waterfront | Walk to Shops

Apartment in Williamstown

10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is HK$1,012
HK$2,153 total
includes taxes & fees
1 Dec - 2 Dec
Downtown | Waterfront | Walk to Shops
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Holiday Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,135
HK$2,937 total
includes taxes & fees
24 Nov - 25 Nov
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
New Studio In Town, By the Water

Apartment in Williamstown

10.0 out of 10, Exceptional, (10)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is HK$934
HK$2,003 total
includes taxes & fees
24 Nov - 25 Nov
New Studio In Town, By the Water
Outdoor dining
2-Bdr Apt In Town, By the Water

Apartment in Williamstown

9.6 out of 10, Exceptional, (11)
"Effortless process! We arrived and felt at home immediately. Could not have been happier with our experience."
United States
Staci A.
The price is HK$934
HK$2,100 total
includes taxes & fees
23 Nov - 24 Nov
2-Bdr Apt In Town, By the Water
TV
Florida Mountain Log Cabin

Holiday Home in Florida

2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is HK$1,430
HK$2,639 total
includes taxes & fees
23 Nov - 24 Nov
Florida Mountain Log Cabin
Pool
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Condo in Hancock

8.0 out of 10, Very good, (8)
"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$1,090
HK$2,652 total
includes taxes & fees
23 Nov - 24 Nov
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cabin in Hinsdale

9.8 out of 10, Exceptional, (33)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is HK$1,282
HK$3,284 total
includes taxes & fees
24 Nov - 25 Nov
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Holiday Home in Sherwood Forest

9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is HK$1,247
HK$3,053 total
includes taxes & fees
24 Nov - 25 Nov
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Exterior
North Getaway Cottage

Holiday Home in Williamstown

9.4 out of 10, Exceptional, (23)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
The price is HK$1,576
HK$3,473 total
includes taxes & fees
24 Nov - 25 Nov
North Getaway Cottage
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"The staff were awesome. Food was great. Room was clean."
Patricia 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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