A large stone church with a tall bell tower and arched windows.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Great Barrington vacation homes

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

1. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ￥36,482
￥56,667 total
includes taxes & fees
Oct 28 - Oct 29
Home in Great Barrington
A staircase with a wooden handrail and a white wall with a light switch.

2. 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 ￥27,789
￥44,659 total
includes taxes & fees
Oct 26 - Oct 27
Leaf-Peeper Paradise in the Berkshires
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is ￥63,336
￥111,248 total
includes taxes & fees
Oct 20 - Oct 21
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.

4. 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 ￥89,636
￥210,312 total
includes taxes & fees
Oct 15 - Oct 16
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

5. 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)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is ￥31,668
￥55,536 total
includes taxes & fees
Oct 18 - Oct 19
Sweet Cozy Victorian in Housatonic. Close to everything.
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

6. 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 ￥28,074
￥67,971 total
includes taxes & fees
Nov 2 - Nov 3
Cheerful 3-bedroom cottage with woodstove
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

7. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (29 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is ￥54,010
￥102,247 total
includes taxes & fees
Oct 20 - Oct 21
Secluded Family Home in Serene Stockbridge Woods
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

8. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is ￥42,910
￥89,205 total
includes taxes & fees
Nov 9 - Nov 10
Treetop Hideaway in Tyringham
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

9. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is ￥80,516
￥138,221 total
includes taxes & fees
Oct 18 - Oct 19
Stylish Mid-century Modern Berkshires Cape
A living room with a sofa, armchairs, a coffee table, and a television.

10. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (11 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 ￥50,305
￥100,407 total
includes taxes & fees
Oct 15 - Oct 16
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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.

11. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥23,086
￥59,392 total
includes taxes & fees
Oct 28 - Oct 29
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern living room with a sofa, armchair, coffee table, and TV.

12. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is ￥46,314
￥95,065 total
includes taxes & fees
Oct 19 - Oct 20
Spacious Central Berkshires Home for Groups
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is ￥49,877
￥109,432 total
includes taxes & fees
Oct 19 - Oct 20
Ellie’s Overlook, best view in the Berkshires!
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

14. 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 ￥11,105
￥49,618 total
includes taxes & fees
Nov 3 - Nov 4
Real Estate: Therapy - Lake, Laundry, Love it
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,366
￥62,291 total
includes taxes & fees
Oct 28 - Oct 29
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A two-story house with a balcony, a deck, and a view of the surrounding forest.

16. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (134 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is ￥46,314
￥96,562 total
includes taxes & fees
Oct 18 - Oct 19
Gorgeous Mountain Views Retreat: Family & Nature
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

17. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is ￥11,084
￥32,935 total
includes taxes & fees
Oct 15 - Oct 16
NEW RENO - Chalet-style farm loft near Tanglewood
A camping setup with a metal chair and a table by a river in a forest.

18. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (16 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is ￥31,668
￥54,444 total
includes taxes & fees
Oct 19 - Oct 20
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden deck with a staircase leading to a covered porch area.

19. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is ￥16,816
￥22,382 total
includes taxes & fees
Oct 19 - Oct 20
All the comforts of home
A cozy living room with a sofa, a fireplace, and large windows.

20. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is ￥55,292
￥100,943 total
includes taxes & fees
Oct 15 - Oct 16
Luxury Barn Near Hudson With New Private Sauna
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 Great Barrington Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Clean room. Special thank you to the cleaning and breakfast staff. Great balcony view. We will come back again."
Christopher 2-night trip
Posted 1 hour ago
The Yankee Inn

Find out more about Great Barrington

Great Barrington Vacation Homes information

Number of reviews
406
Accommodation
520 Vacation Homes
Lowest Price
￥22,382
Highest Price
￥210,312