Photo by Ed Gaffny

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Compare 74 Apartments in Cheshire with updated reviews, rates, and availability.

Lovely two bedroom river-view rental unit
Property grounds

Lovely two bedroom river-view rental unit

9.2 out of 10, Wonderful, (19)
"Typical New England older home. 2nd floor unit. Comfy beds, well-stocked kitchen (that did remind me a bit of my first place out of college). This is definitely not The Ritz, but the linens were soft and the place worked for us."
The price is AED 551
AED 1,169 total
includes taxes & fees
25 Nov - 26 Nov
Lovely two bedroom river-view rental unit
Park Street Penthouse Apartment
Private kitchen

Park Street Penthouse Apartment

9.0 out of 10, Wonderful, (2)
"Like exploring new areas. Quaint town with a few restaurants and a diner in walking distance. Huge apt - well more than needed for one night … clean and has everything you would need to stay longer including laundry and full kitchen. Little hot bc only has window AC units as it’s an old art deco building. Close driving to my resorts and things to do in zbershired"
The price is AED 716
AED 1,260 total
includes taxes & fees
25 Nov - 26 Nov
Park Street Penthouse Apartment
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Interior

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (3)
"The property was clean, well equipped, and very comfortable. We had ample parking for our car and our son's car right outside the door, with room for our other son to park when he visited us. It is beautifully decorated with paintings and art objects, many with an Asian theme. It's close to the Shelburne Falls village and to Route 2 for touring the area, but it was very quiet at night, lending itself to very restful sleeps over night. Host was very available and helpful! Hope to stay there...
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Charming Apartment In Berkshire Victorian Home
Exterior

Charming Apartment In Berkshire Victorian Home

7.8 out of 10, Good, (7)
"This adorable place is central to Pittsfield and made it really easy for my daughter and I go get where we needed to be. It’s a clean, great space. We’ll definitely be back!"
Charming Apartment In Berkshire Victorian Home
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Beautiful State of Art Kitchen Awaits in this spacious 900 Sq FT Suite

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (20)
"We had a lovely time at this large and welcoming condo. It was easy to find, had all the amenities we needed and was just the perfect place for an off-season get away. Would easily re-book at any time during the year. "
The price is AED 577
AED 1,167 total
includes taxes & fees
19 Dec - 20 Dec
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
2-Bdr Apt In Town, By the Water
Private kitchen

2-Bdr Apt In Town, By the Water

9.4 out of 10, Exceptional, (3)
"Lovely property, in good shape. Close to many Williamstown attractions."
The price is AED 441
AED 905 total
includes taxes & fees
25 Nov - 26 Nov
2-Bdr Apt In Town, By the Water
Private 1-bedroom apartment in enchanting North Adams with WiFi.
Living area

Private 1-bedroom apartment in enchanting North Adams with WiFi.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Dianne was great and accommodating. Check in was so easy and the apartment was more spacious than expected! Very clean, neat, and organized. She made our stay at North Adams welcoming and would definitely book again. Thank you so much! "
The price is AED 602
AED 931 total
includes taxes & fees
30 Nov - 1 Dec
Private 1-bedroom apartment in enchanting North Adams with WiFi.
Garfield House Studio at 208
Exterior

Garfield House Studio at 208

9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
Garfield House Studio at 208
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (60)
"Beautiful property with flower farm, pick your own berries and vegetable farm stand. Rustic log cabin feel with all amenities needed with kitchen."
The price is AED 533
AED 797 total
includes taxes & fees
25 Nov - 26 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Private apartment in beautiful country barn
Living area

Private apartment in beautiful country barn

10.0 out of 10, Exceptional, (18)
"Great farmhouse in the Berkshires. Location is out of the way without being out of the way. Communications with the host is great. Very accommodating."
Private apartment in beautiful country barn
New Studio In Town, By the Water
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

New Studio In Town, By the Water

10.0 out of 10, Exceptional, (3)
"Great location"
The price is AED 441
AED 859 total
includes taxes & fees
25 Nov - 26 Nov
New Studio In Town, By the Water
Vacation Rental Home in the Berkshires!
Williamstown Vacation Rental | Studio | 1BA | Stairs Required | 1,000 Sq Ft

Vacation Rental Home in the Berkshires!

9.6 out of 10, Exceptional, (10)
"Beautiful property, amazing views, lots of privacy, home is nicely decorated and had everything we needed and more. Will definitely visit again!"
Vacation Rental Home in the Berkshires!
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

9.2 out of 10, Wonderful, (9)
"Such a awesome facility! Love the room, the Jiminy property is very cool and you don’t even need to leave to go anywhere else because there is so much to do here. Stay."
The price is AED 382
AED 835 total
includes taxes & fees
25 Nov - 26 Nov
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Main Street Delight 1bedroom
Living area

Main Street Delight 1bedroom

10.0 out of 10, Exceptional, (18)
"The location was fantastic for our stay in the Berkshires. Walkable to many restaurants & shops. It was very well decorated & cozy. Very convenient being above a coffee shop, however not ideal if you enjoy sleeping in. We could hear the consistent squeaking of the coffee shop door as soon as it opened in the morning (~7:00 am) from the bedroom. However, good motivation to get up and enjoy the beautiful Berkshires!"
Main Street Delight 1bedroom
Heart of Lenox!! - renovated downtown apartment
Private kitchen

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (63)
"The bathroom was less than tidy and when I recall it was like that last time. Bathroom rug is dirty or just dirty looking. I advise property Meg to buy several Along with a Terry bath mat so you can cover it when using. No little extras like soap/shampoo are offered. I had My own. Overall the apartment is very cute would stay again. "
Heart of Lenox!! - renovated downtown apartment
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Comfortable Living Room with Pullout Queen Sofa Bed and Smart TV with Full DVD Library and Board Game library for those nights in.

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

9.6 out of 10, Exceptional, (29)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
The price is AED 382
AED 835 total
includes taxes & fees
25 Nov - 26 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Vacation Rental Home in the Berkshires!
Living area

Vacation Rental Home in the Berkshires!

3.0 star property
Vacation Rental Home in the Berkshires!
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Fully Redone Suite with master King Bed

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

10.0 out of 10, Exceptional, (2)
"Stayed one night at one of my favorite ski spots. Will be back again!"
The price is AED 382
AED 835 total
includes taxes & fees
25 Nov - 26 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Gateway to the Berkshires - Renovated downtown apartment
Room

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (7)
"Thanks, Emmy, for a great visit. The apartment was exactly what we hoped for, clean and convenient to downtown and to all things in the Berkshires. We explored and relaxed and thoroughly enjoyed our getaway over a beautiful October weekend. I'd recommend the apartment to anyone who wants that in-town setting and wishes to explore all that the area has to offer. Great host, thank you!"
Gateway to the Berkshires - Renovated downtown apartment
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
Living area

Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Was a great spot to enjoy Jiminy Peak!"
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
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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Other property types in Cheshire

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is AED 620
AED 717 total
includes taxes & fees
25 Nov - 26 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 547
AED 600 total
includes taxes & fees
25 Nov - 26 Nov
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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.

Frequently asked questions

What's it like to stay at an apartment in Cheshire?
You might have as many choices centrally in Cheshire, but Expedia can help you locate lodging options in the area with similar amenities to an apartment. 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: Lovely two bedroom river-view rental unit: Situated in Williamstown, 11.5 mi/18.5 km from the heart of Cheshire. Includes sofa beds. New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.: Located 14.1 mi/22.6 km away in Richmond. New Studio In Town, By the Water: It’s situated in Williamstown, 10.3 mi/16.5 km away. Includes free WiFi, private balconies, and sofa beds. Downtown | Waterfront | Walk to Shops: Located in Williamstown, 10.3 mi/16.5 km from Cheshire. Includes free WiFi, private balconies, and sofa beds. Access to a fitness center is available on site.
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?
Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Mount Greylock State Reservation. 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.