Vacation Rentals in Berkshire County

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Top Vacation Rentals in Berkshire County

Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2124)
"Clean and great pool and hot tub facilities "
United States
Alyce
The price is ￥14,029
￥17,349 total
includes taxes & fees
Nov 12 - Nov 13
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (984)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
United States
Sandhya
The price is ￥22,790
￥25,456 total
includes taxes & fees
Nov 9 - Nov 10
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

Huttopia Berkshires

1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
The Ponds at Foxhollow
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
8.8 out of 10, Excellent, (3)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥30,972
￥45,530 total
includes taxes & fees
Nov 9 - Nov 10
Pet Friendly Riverfront Home in Great Barrington
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

The Kemble- Built by a US Secretary of State in Lenox

Lenox
10.0 out of 10, Exceptional, (17)
"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...
United Kingdom
Carrie S.
The Kemble- Built by a US Secretary of State in Lenox
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
United States
Jim O.
The price is ￥91,617
￥169,937 total
includes taxes & fees
Nov 18 - Nov 19
Hancock Village Inn Near Jiminy Peak
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
9.2 out of 10, Wonderful, (32)
"Beautiful property with tons of space and fantastic for a group of friends or family"
United States
Greg S.
Amore Estate - beautiful room with many places to explore and relax in.
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
10.0 out of 10, Exceptional, (132)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Interior
Peace and quiet on the lake

Peace and quiet on the lake

Sherwood Forest
9.6 out of 10, Exceptional, (227)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
9.8 out of 10, Exceptional, (149)
"You'll do some walking and stair climbing but otherwise was just what we needed and wanted! Owner was very accommodating when we had to bring the grandpup unexpectedly. Definitely recommend staying here."
United States
Wendy Cameron L.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Interior
Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass

Otis
8.6 out of 10, Excellent, (9)
"The house’s position on the water, being further out than all other surrounding homes, makes for beautiful views of the lake and all it activities. The sunrises are beautiful. Unfortunately when you don’t have proper running water and a toilet that flushes without having to put water in the tank almost every time, the experience is less than ideal. The host warned us of the toilet about 15 min before we arrived and never had the kitchen sink fixed in the 5 days we stayed. That was rather...
United States
Colleen W.
Private Island - Largest Fresh Water Reservoir in Mass
Property grounds
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Hancock
9.8 out of 10, Exceptional, (70)
"Nice house; good location near Jimney Peak and Mt. Greylock. Enjoyed my stay very much."
United States
Ted S.
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Exterior
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield
9.8 out of 10, Exceptional, (93)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
United States
Sharon S.
Antique Farmhouse Totally Restored
Fridge, microwave, oven, stovetop
The Greylock Cabin

The Greylock Cabin

Florida
10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay at Greylock Cabin! It is clean, well maintained, and was very prepared for our arrival. Extra towels, bedding, and basic cookware were helpful for a comfortable getaway. It was easy to access the cabin and park. The host was very communicative and easy to reach throughout our stay. The outdoor space had a great view and was perfect to grill and unwind by the fire."
United States
Robert G.
The price is ￥36,134
￥61,934 total
includes taxes & fees
Nov 11 - Nov 12
The Greylock Cabin
Property grounds
Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires

Lenox
10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
Exterior
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield
10.0 out of 10, Exceptional, (62)
"We stayed at this house for a long weekend. It was beautiful. The views are spectacular. The house is well stocked. And we thoroughly enjoyed our stay and can’t wait to come back."
United States
Samantha R.
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Interior
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

New Marlborough
9.6 out of 10, Exceptional, (17)
"House was adorable! Very clean and updated, perfect size for a family. Great location in the heart of the Berkshires."
United States
Laura B.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Exterior
Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town

Lenox
10.0 out of 10, Exceptional, (76)
"Nice place in a convenient location."
United States
Eileen P.
Enjoy comfortable elegance in this secluded grand home located in town
Property grounds
Chic Pittsfield Home With A View!

Chic Pittsfield Home With A View!

Pittsfield
8.2 out of 10, Very Good, (11)
"Great view from the property, lovely house and yard. Coiuldn't have been a better stay. "
United States
Lara W.
Chic Pittsfield Home With A View!
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 Berkshire County Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
Jamie 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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Vacation Apartments in Berkshire County

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