A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Cheshire vacation homes

Pool

1. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is ￥25,467
￥85,811 total
includes taxes & fees
Oct 8 - Oct 9
Comfortable Berkshires retreat on mtn resort, SISO
A wooden deck with a table and chairs, surrounded by a white railing.

2. 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
8.4 out of 10, Very good, (10 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 ￥42,494
￥77,804 total
includes taxes & fees
Oct 17 - Oct 18
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

3. 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 ￥11,073
￥32,725 total
includes taxes & fees
Oct 8 - Oct 9
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

4. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is ￥13,603
￥35,786 total
includes taxes & fees
Nov 2 - Nov 3
1800s Carriage house in Berkshires / Hudson Valley
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

5. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (9 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is ￥18,333
￥32,382 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Home in Pownal VT
A kitchen with white cabinets, a wooden dining table, and pendant lights.

6. 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 ￥36,223
￥76,682 total
includes taxes & fees
Oct 13 - Oct 14
A roomy remodeled retreat close to MassMoCA
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

7. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is ￥27,792
￥88,516 total
includes taxes & fees
Oct 12 - Oct 13
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

8. 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 ￥47,965
￥97,713 total
includes taxes & fees
Oct 20 - Oct 21
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

9. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ￥99,487
￥181,745 total
includes taxes & fees
Oct 13 - Oct 14
Hancock Village Inn Near Jiminy Peak
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

10. 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 ￥45,674
￥74,482 total
includes taxes & fees
Oct 12 - Oct 13
Greylock Cabin
A white two-story house with a porch, surrounded by trees and a hill.

11. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is ￥35,591
￥79,261 total
includes taxes & fees
Nov 2 - Nov 3
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

12. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is ￥21,259
￥36,644 total
includes taxes & fees
Oct 28 - Oct 29
Private bed with En-suite bathroom Marigold Room
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.

13. 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 ￥25,198
￥61,894 total
includes taxes & fees
Oct 8 - Oct 9
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is ￥49,827
￥109,322 total
includes taxes & fees
Oct 14 - Oct 15
Ellie’s Overlook, best view in the Berkshires!
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

15. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
5BR Berkshire Home Mins To The Mountain
A living room with a sofa, armchairs, a coffee table, and a television.

16. 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 ￥50,168
￥100,311 total
includes taxes & fees
Oct 20 - Oct 21
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

17. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is ￥43,974
￥90,821 total
includes taxes & fees
Oct 27 - Oct 28
NEW RENO Historic Creamery in Berkshires w/hot tub
A hallway with wooden flooring, white walls, and a bed in the background.

18. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is ￥33,161
￥67,557 total
includes taxes & fees
Oct 19 - Oct 20
Cozy private 2 bed apartment in Shelburne Falls
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

19. 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 ￥80,435
￥138,082 total
includes taxes & fees
Oct 18 - Oct 19
Stylish Mid-century Modern Berkshires Cape
A modern living room with a sofa, armchair, coffee table, and TV.

20. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.4 out of 10, Exceptional, (3 reviews)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is ￥46,268
￥93,379 total
includes taxes & fees
Oct 12 - Oct 13
Spacious Central Berkshires Home for Groups
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 Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Very spacious and inviting..Loved the coffee maker in lobby!!!! All the girls at the front desk were extremely nice and welcoming. Very clean property and great location.. to Great Barrington, Lenox, Stockbridge, and Lee with great restaurants near by in those towns as well"
Frank 2-night trip
Posted 17 hours ago
Berkshire Mountain Lodge

Find out more about Cheshire

Cheshire Vacation Homes information

Number of reviews
173
Accommodation
292 Vacation Homes
Lowest Price
￥32,382
Highest Price
￥181,745