Cheshire Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Cheshire holiday rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,675 reviews)
"Love this place for a weekend getaway."
United States
Jacob
The price is HK$746
HK$920 total
includes taxes & fees
27 Sept - 28 Sept
Vacation Village in the Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,154 reviews)
"Clean & comfortable stay"
United States
Robert
The price is HK$624
HK$873 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

3. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is HK$1,546
HK$3,427 total
includes taxes & fees
27 Sept - 28 Sept
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

4. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (15 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is HK$1,137
HK$2,102 total
includes taxes & fees
27 Sept - 28 Sept
Penthouse Apartment on Park Street
A snow-covered outdoor area with a fire pit, tables, and chairs.

5. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is HK$833
HK$1,798 total
includes taxes & fees
27 Sept - 28 Sept
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

6. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (33 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is HK$1,165
HK$2,571 total
includes taxes & fees
8 Oct - 9 Oct
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

7. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is HK$833
HK$1,798 total
includes taxes & fees
27 Sept - 28 Sept
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

8. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is HK$812
HK$1,774 total
includes taxes & fees
29 Sept - 30 Sept
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
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 HK$4,521
HK$7,973 total
includes taxes & fees
29 Sept - 30 Sept
Hancock Village Inn Near Jiminy Peak
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

10. 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 HK$2,429
HK$3,926 total
includes taxes & fees
6 Oct - 7 Oct
The Greylock Cabin
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

11. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
The price is HK$1,108
HK$2,281 total
includes taxes & fees
29 Sept - 30 Sept
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

12. 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 HK$1,263
HK$4,246 total
includes taxes & fees
6 Oct - 7 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

13. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is HK$819
HK$1,782 total
includes taxes & fees
28 Sept - 29 Sept
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Four people seated at a table with food and drinks, wearing winter sports helmets.

14. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is HK$833
HK$1,798 total
includes taxes & fees
27 Sept - 28 Sept
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

15. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is HK$833
HK$1,798 total
includes taxes & fees
27 Sept - 28 Sept
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A wooden deck with a table and chairs, surrounded by a white railing.

16. 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 HK$2,345
HK$3,916 total
includes taxes & fees
19 Oct - 20 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

17. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is HK$791
HK$1,750 total
includes taxes & fees
27 Sept - 28 Sept
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

18. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is HK$1,757
HK$4,346 total
includes taxes & fees
6 Oct - 7 Oct
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A bedroom with a wooden bed, a window with a view of trees, and a red chair.

19. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is HK$1,098
HK$1,567 total
includes taxes & fees
28 Sept - 29 Sept
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

20. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
The price is HK$1,151
HK$2,030 total
includes taxes & fees
29 Sept - 30 Sept
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
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

Frequently asked questions

Can I find a holiday rental in Cheshire?

Yes, there are holiday rentals close to the most popular sights in Cheshire, or you can select a more secluded option if you're looking for a relaxing stay. Cheshire is known for its ski areas and restaurants. Make sure you have time to check out the lake views and shopping during your trip.

What are some of the best holiday rentals that Cheshire has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Cheshire is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay.

How many holiday rentals are there in Cheshire?

Expedia has 5 holiday rentals for your stay in Cheshire.

What can I see and do in Cheshire?

Mount Greylock State Reservation and Cheshire Reservoir are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.

What are holiday rentals like in Cheshire?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cheshire. Holiday rentals feature extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family gatherings.