A lake surrounded by autumn-colored trees and hills.

Cheshire Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Cheshire holiday rentals

Indoor pool

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,844 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is HK$630
HK$790 total
includes taxes & fees
15 Nov - 16 Nov
Vacation Village in the Berkshires
A large building with a prominent tower, surrounded by trees and a winding road.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,269 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is HK$602
HK$848 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
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.

3. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (19 reviews)
"Great penthouse apartment with interesting artwork throughout. Location convenient to local attractions; a five minutes easy drive to Mass MOCA. The apartment was impeccably clean and the host was very responsive to questions we had during our stay. Would love to stay again."
United States
Lisa M.
The price is HK$1,137
HK$2,086 total
includes taxes & fees
24 Nov - 25 Nov
Penthouse Apartment on Park Street
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

4. 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, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
United States
Marcia O.
The price is HK$883
HK$2,344 total
includes taxes & fees
17 Nov - 18 Nov
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A cozy living room with a large window, wooden walls, and a television.

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$755
HK$1,659 total
includes taxes & fees
15 Nov - 16 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

6. 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$755
HK$1,659 total
includes taxes & fees
15 Nov - 16 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A wooden deck with a table and chairs, surrounded by a white railing.

7. 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 HK$2,111
HK$3,707 total
includes taxes & fees
21 Nov - 22 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

8. 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, (41 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$1,532
HK$3,446 total
includes taxes & fees
15 Nov - 16 Nov
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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 HK$1,263
HK$3,861 total
includes taxes & fees
14 Nov - 15 Nov
Comfortable Berkshires retreat on mtn resort, SISO
A spacious living area with a stone fireplace, comfortable seating, and a view of the kitchen.

10. UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
9.8 out of 10, Exceptional, (18 reviews)
"lovely place to stay"
United States
Nancy P.
The price is HK$2,464
HK$4,382 total
includes taxes & fees
27 Nov - 28 Nov
UNIQUE - 1BR Country Condo @ Jiminy Peak
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

11. 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$755
HK$1,659 total
includes taxes & fees
15 Nov - 16 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

12. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (14 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is HK$755
HK$1,659 total
includes taxes & fees
15 Nov - 16 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

13. 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, (19 reviews)
"It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended."
United States
David
The price is HK$839
HK$1,770 total
includes taxes & fees
16 Nov - 17 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A bedroom with a large bed, a nightstand, a dresser, a window with curtains, and a wall with a deer painting.

14. 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$755
HK$1,659 total
includes taxes & fees
15 Nov - 16 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
A row of multi-story buildings with a uniform architectural style, likely a hotel or resort, set against a backdrop of green hills and trees.

15. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"Great place, everything was so easy!!"
United States
Dana
The price is HK$755
HK$1,659 total
includes taxes & fees
15 Nov - 16 Nov
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
A wooden deck with outdoor furniture, a glass door leading to a view of a grassy area with trees.

16. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
8.0 out of 10, Very good, (1 review)
"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...
United States
Cecilia S.
The price is HK$1,059
HK$2,208 total
includes taxes & fees
15 Nov - 16 Nov
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Work desk

17. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.2 out of 10, Wonderful, (23 reviews)
"Perfect check in process, spotlessly clean, gorgeous property, and I wish I had had enough time to relax by the water. Best experience I've had, and I will definitely stay there again."
United States
Andrea
The price is HK$1,083
HK$2,270 total
includes taxes & fees
15 Nov - 16 Nov
2-Bdr Apt In Town, By the Water
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

18. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (35 reviews)
"We really enjoyed our stay it was a very nice place for a family."
United States
Shmaya G.
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
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.

19. 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$1,106
HK$2,050 total
includes taxes & fees
17 Nov - 18 Nov
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A living room with a blue sofa, a TV on a stand, a small table with a lamp, and a window with curtains.

20. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (13 reviews)
"Great location, very clean, included washer dryer, picnic area by river, large parking space."
United States
Douglas
The price is HK$1,110
HK$2,256 total
includes taxes & fees
15 Nov - 16 Nov
Downtown | Waterfront | Walk to Shops
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Breakfast was h asic everything else was perfect"
paul 2-night trip
Posted 15 hours ago
The Yankee Inn

Find out more about Cheshire

Search for holiday rentals in Cheshire on Expedia! You can easily find your home rentals, villas, holiday apartments in Cheshire using one of the methods below:

  • View our selection of featured holiday rentals in Cheshire
  • Use the map to find apartments and other holiday homes in the Cheshire neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cheshire while they last

Look no further and take a look at our great range of rental properties in Cheshire!

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.