A lake surrounded by autumn-colored trees and hills.

Holiday Homes in Cheshire

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Cheshire holiday homes

A heated 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 €475
includes taxes & fees
21 Sept - 22 Sept
Comfortable Berkshires retreat on mtn resort, SISO
Outdoor dining

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 clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is €446
includes taxes & fees
17 Oct - 18 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Dining

3. 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 €161
includes taxes & fees
27 Sept - 28 Sept
Cozy Home in Pownal VT
Coffee/tea maker, fridge, microwave, oven

4. 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)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is €186
includes taxes & fees
20 Sept - 21 Sept
NEW RENO - Chalet-style farm loft near Tanglewood
Dining

5. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (60 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is €413
includes taxes & fees
21 Sept - 22 Sept
A roomy remodeled retreat close to MassMoCA
Coffee/tea maker, fridge, microwave, stovetop

6. 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 €483
includes taxes & fees
21 Sept - 22 Sept
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
TV, DVD player, books, video library

7. 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 €211
includes taxes & fees
20 Sept - 21 Sept
1800s Carriage house in Berkshires / Hudson Valley
Dining

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 €515
includes taxes & fees
20 Sept - 21 Sept
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Outdoor dining

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 €979
includes taxes & fees
21 Sept - 22 Sept
Hancock Village Inn Near Jiminy Peak
Exterior

10. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is €283
includes taxes & fees
20 Sept - 21 Sept
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Exterior

11. The Greylock Cabin

The 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 €464
includes taxes & fees
20 Oct - 21 Oct
The Greylock Cabin
Exterior

12. 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 €425
includes taxes & fees
5 Oct - 6 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Interior

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 €325
includes taxes & fees
29 Sept - 30 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Smart TV, fireplace, books

14. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (7 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is €593
includes taxes & fees
21 Sept - 22 Sept
5BR Berkshire Home Mins To The Mountain
Exterior

15. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
Two Brooks Lodge
Exterior

16. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is €193
includes taxes & fees
28 Sept - 29 Sept
Private bed with En-suite bathroom Marigold Room
Iron/ironing board, WiFi, bed sheets

17. 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 €324
includes taxes & fees
20 Sept - 21 Sept
Cozy private 2 bed apartment in Shelburne Falls
Exterior

18. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is €466
includes taxes & fees
22 Sept - 23 Sept
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Outdoor dining

19. 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, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is €461
includes taxes & fees
29 Sept - 30 Sept
NEW RENO Historic Creamery in Berkshires w/hot tub
Smart TV

20. Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit

Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit
Averill Park
The price is €598
includes taxes & fees
20 Sept - 21 Sept
Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"What a gem!! Beautiful patio and lobby. Rooms were so well appointed and staff was very helpful. Great spot if you’re attending an event at Tanglewood."
Sheree 1-night trip
Posted 2 hours ago
Berkshires Untold

Find out more about Cheshire

Cheshire Holiday Homes information

Number of reviews
204
Accommodation
292 Holiday Homes
Lowest Price
€161
Highest Price
€979