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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for The Berkshires vacation homes

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

1. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥23,035
￥59,261 total
includes taxes & fees
Oct 29 - Oct 30
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A hot tub with a string of lights above it, set against a dark night sky.

2. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,230
￥61,957 total
includes taxes & fees
Nov 5 - Nov 6
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

3. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is ￥9,163
￥47,119 total
includes taxes & fees
Nov 2 - Nov 3
Real Estate: Therapy - Lake, Laundry, Love it
A dining area with a wooden table, chairs, and a ceiling fan.

4. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is ￥31,892
￥49,873 total
includes taxes & fees
Nov 4 - Nov 5
Leaf-Peeper Paradise in the Berkshires
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ￥34,018
￥52,247 total
includes taxes & fees
Nov 9 - Nov 10
Home in Great Barrington
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

6. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is ￥42,680
￥88,894 total
includes taxes & fees
Nov 9 - Nov 10
Treetop Hideaway in Tyringham
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

7. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥27,923
￥67,255 total
includes taxes & fees
Nov 3 - Nov 4
Cheerful 3-bedroom cottage with woodstove
A dining area with a wooden table, black chairs, and a vase with green plants.

8. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is ￥31,498
￥54,887 total
includes taxes & fees
Nov 1 - Nov 2
Sweet Cozy Victorian in Housatonic. Close to everything.
Pool

9. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is ￥25,356
￥85,260 total
includes taxes & fees
Oct 29 - Oct 30
Comfortable Berkshires retreat on mtn resort, SISO
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

10. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is ￥53,720
￥101,698 total
includes taxes & fees
Nov 2 - Nov 3
Secluded Family Home in Serene Stockbridge Woods
A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

11. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...
United States
Delaney M.
The price is ￥49,609
￥108,844 total
includes taxes & fees
Nov 3 - Nov 4
Ellie’s Overlook, best view in the Berkshires!
A living room with a sofa, armchairs, a coffee table, and a television.

12. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is ￥50,035
￥99,340 total
includes taxes & fees
Oct 29 - Oct 30
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A kitchen with white cabinets, a wooden dining table, and pendant lights.

13. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is ￥36,065
￥75,820 total
includes taxes & fees
Oct 30 - Oct 31
A roomy remodeled retreat close to MassMoCA
A modern living room with a sofa, armchair, coffee table, and TV.

14. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
The price is ￥46,066
￥93,852 total
includes taxes & fees
Nov 1 - Nov 2
Spacious Central Berkshires Home for Groups
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

15. 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, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
The price is ￥72,675
￥133,768 total
includes taxes & fees
Nov 23 - Nov 24
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

16. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ￥63,783
￥111,531 total
includes taxes & fees
Nov 16 - Nov 17
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

17. 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, (9 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 ￥89,155
￥209,183 total
includes taxes & fees
Oct 30 - Oct 31
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

18. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is ￥42,522
￥89,950 total
includes taxes & fees
Oct 29 - Oct 30
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A wooden deck with a table and chairs, surrounded by a white railing.

19. 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
8.6 out of 10, Excellent, (11 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is ￥42,381
￥77,597 total
includes taxes & fees
Oct 29 - Oct 30
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

20. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is ￥45,278
￥73,936 total
includes taxes & fees
Nov 1 - Nov 2
Greylock Cabin
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"Clean and comfortable"
Robert 1-night trip
Posted 5 hours ago
Berkshire Mountain Lodge

Find out more about The Berkshires

The Berkshires Vacation Homes information

Number of reviews
314
Accommodation
336 Vacation Homes
Lowest Price
￥47,119
Highest Price
￥209,183

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