A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Cheshire apartments

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.

1. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (14 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 CA $200
CA $384 total
includes taxes & fees
Aug 23 - Aug 24
Penthouse Apartment on Park Street
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

2. 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, (31 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
The price is CA $180
CA $442 total
includes taxes & fees
Aug 31 - Sep 1
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

3. 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, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is CA $156
CA $333 total
includes taxes & fees
Aug 24 - Aug 25
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

4. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location"
United States
Alicia S.
The price is CA $156
CA $333 total
includes taxes & fees
Aug 25 - Aug 26
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

5. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is CA $155
CA $331 total
includes taxes & fees
Aug 25 - Aug 26
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

6. 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, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is CA $156
CA $333 total
includes taxes & fees
Aug 24 - Aug 25
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

7. 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 CA $156
CA $333 total
includes taxes & fees
Aug 24 - Aug 25
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

8. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (18 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is CA $172
CA $377 total
includes taxes & fees
Sep 15 - Sep 16
New Studio In Town, By the Water
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

9. 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 CA $147
CA $321 total
includes taxes & fees
Aug 24 - Aug 25
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

10. 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 CA $208
CA $377 total
includes taxes & fees
Aug 26 - Aug 27
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A living room with a sofa, armchair, coffee table, and a TV on a stand.

11. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is CA $155
CA $331 total
includes taxes & fees
Aug 25 - Aug 26
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

12. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (9 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is CA $186
CA $404 total
includes taxes & fees
Aug 23 - Aug 24
Downtown | Waterfront | Walk to Shops

13. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.2 out of 10, Wonderful, (16 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is CA $172
CA $395 total
includes taxes & fees
Aug 24 - Aug 25
2-Bdr Apt In Town, By the Water
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

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 CA $156
CA $333 total
includes taxes & fees
Aug 24 - Aug 25
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Cherry Plain State Park with a sandy beach, people relaxing, and a lake.

15. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (4 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is CA $192
CA $374 total
includes taxes & fees
Aug 23 - Aug 24
Berkshires Apartment at the Stephentown Hotel
A living room with a sofa, armchairs, a TV, a fireplace, and a large window.

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 CA $245
CA $483 total
includes taxes & fees
Aug 31 - Sep 1
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

17. Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Great location on mountain and great communication by unit owner."
United States
Marc F.
The price is CA $156
CA $333 total
includes taxes & fees
Aug 24 - Aug 25
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

18. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is CA $133
CA $303 total
includes taxes & fees
Aug 24 - Aug 25
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A Country Inn with a large, welcoming entrance and multiple parking spaces.

19. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Everything was wonderful…"
United States
Alyne K.
The price is CA $155
CA $331 total
includes taxes & fees
Aug 25 - Aug 26
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

20. 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)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is CA $219
CA $452 total
includes taxes & fees
Aug 23 - Aug 24
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
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 Whitlock

The Whitlock

8/10 Good
"The Whitlock is a lovely old inn, located right in the heart of Lenox and walkable to everything in town. The staff is also lovely. Our room was spacious and well layed out. [but for an ADA compliant walk in shower, you need more than grab bars - a rubber matt in the shower is a necessity!!] However, for a hotel that calls itself hi-end, it fell far short of that mark. First and foremost, the email communications with both Hotels.com and the The Whitlock were like a Marx Brothers skit: We were first told the check in would be at the Constance down the street, not at the Whitlock. When I asked the off-shore "team" about that, I was told that the Whitlock was under new management and no longer had off-site check-in. The additional info we received with attached links also did not work - the response: it will work the day of check in!!?? [ps - they were not "live" links, just a series of numbers and letters] It's great to try and streamline operations, but those operations MUST work, and the responses from the team must make sense!!!"
Paula M. 2-night trip
Posted 1 hour ago
The Whitlock

Find out more about Cheshire

Cheshire Apartments information

Number of reviews
238
Accommodation
96 Apartments
Lowest Price
CA $303
Highest Price
CA $483

Frequently asked questions

What's it like to stay at an apartment in Cheshire?
You'll find 6 accommodations in Cheshire. Though there aren't many apartments, we can help you find similar accommodations. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. Even filter by similar properties such as vacation homes, condos, or guest houses.
How do you know if an apartment is a good option for you?
An apartment features a kitchen for convenient meals, and often has more space than a traditional hotel room. Apartments are a good option for solo travelers who want to stay in at night and plan out their next day, and also for families who want the conveniences of home.
What's a favorite apartment for a stay in Cheshire?
Listed below are some of the favorite apartments in the area to choose from: Getaway Near Mass MoCA, Great Hiking, Scenic Views: Located in Stamford, 14 mi/22.5 km from the heart of Cheshire. Includes free WiFi. Access to onsite laundry facilities is available on site. FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!: Located 16.3 mi/26.2 km away in Pownal. A private pool, free WiFi, and private patios are included. Onsite laundry facilities and an outdoor pool are on site. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake: Located in Whitingham, 21.2 mi/34.1 km away. Includes private balconies, fireplaces, and Smart TVs. Free breakfast and onsite laundry facilities are on site. Downtown | Waterfront | Walk to Shops: Located 10.3 mi/16.5 km away in Williamstown. Free WiFi, private balconies, and sofa beds are included. A fitness center and onsite laundry facilities are on site. Penthouse Apartment on Park Street: It's situated in Adams, 4.7 mi/7.6 km from Cheshire.
What can I expect from the weather during my trip to Cheshire?
Weather is only one factor, but it can really affect your travel plans, especially when you are planning a longer stay in Cheshire. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What should 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. St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center are a couple of places you'll find in the larger area.
What's the best way to get to and around Cheshire?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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