Photo by Photo courtesy of Berkshire Visitors Bureau

The Berkshires Holiday Rentals

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Check prices for these dates

Tonight
25 Nov - 26 Nov
Tomorrow
26 Nov - 27 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Holiday Rentals in The Berkshires

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2147)
"Great place!"
United States
Nicole
The price is HK$576
HK$729 total
includes taxes & fees
29 Nov - 30 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$1,148
HK$1,283 total
includes taxes & fees
26 Nov - 27 Nov
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

Camping in Williamstown

1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is HK$1,218
HK$1,361 total
includes taxes & fees
14 Dec - 15 Dec
Huttopia Berkshires
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
Games room
Pet Friendly Riverfront Home in Great Barrington

Holiday Home in Great Barrington

9.2 out of 10, Wonderful, (5)
The price is HK$1,576
HK$2,317 total
includes taxes & fees
1 Dec - 2 Dec
Pet Friendly Riverfront Home in Great Barrington
Interior
Peace and quiet on the lake

Holiday Home in Sherwood Forest

9.6 out of 10, Exceptional, (229)
"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
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

Villa in 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
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Holiday Home in 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!
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Holiday Home in Stockbridge

10.0 out of 10, Exceptional, (134)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Holiday Home in Hancock

9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is HK$2,506
HK$5,701 total
includes taxes & fees
26 Nov - 27 Nov
Comfortable Berkshires retreat on mtn resort, SISO
Exterior
Hancock Village Inn Near Jiminy Peak

Holiday Home in Hancock

10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is HK$4,661
HK$8,646 total
includes taxes & fees
2 Dec - 3 Dec
Hancock Village Inn Near Jiminy Peak
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Holiday Home in 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
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

Holiday Home 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.
Interior
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Holiday Home in 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
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$4,031
HK$6,128 total
includes taxes & fees
24 Dec - 25 Dec
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior
Antique Farmhouse Totally Restored

Holiday Home in 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
Property grounds
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Holiday Home in 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
Fridge, microwave, oven, stovetop
The Greylock Cabin

Holiday Home in Florida

10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is HK$2,043
HK$3,404 total
includes taxes & fees
9 Dec - 10 Dec
The Greylock Cabin
Interior
Private Island - Largest Fresh Water Reservoir in Mass

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

Holiday Home in 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
The price is HK$4,426
HK$10,368 total
includes taxes & fees
30 Nov - 1 Dec
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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 Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"We loved the room!! Very comfy bed !"
Cortney 1-night trip
Posted 3 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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