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

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!
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
30 Dec - 31 Dec
Cozy Rustic Apt in 18th c Berkshire Farmhouse
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 1,173 total
includes taxes & fees
2 Jan - 3 January 2025
Lovely two bedroom river-view rental unit
The Penthouse, Downtown Lenox by Evergreen Home
Gorgeous open concept living room

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (6)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Exterior

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (59)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (31)
"The space was cozy and clean and the owners were very easy to communicate with and knowledgeable about the area. The bathroom has very fun lights. "
The price is AED 533
AED 797 total
includes taxes & fees
30 Dec - 31 Dec
Charming Apt in 18th c Berkshire Farmhouse
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Interior

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

10.0 out of 10, Exceptional, (6)
"Comfortable and spacious, in a lovely setting. "
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
Kitchen comes fully stocked with all essentials. Gas stove, double side fridge, dishwasher, Keurig machine, etc.

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

10.0 out of 10, Exceptional, (1)
"We stayed here because we had Tanglewood tickets which turned out to be a great stay… It was a beautiful drive getting there and close enough to Tanglewood. Our host gave wonderful advice on where to eat and places to go. Thanks so much for sharing your place with us. Would absolutely consider going back "
The price is AED 1,157
AED 2,207 total
includes taxes & fees
31 Dec - 1 January 2025
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
Upstairs on Main
Exterior

Upstairs on Main

9.2 out of 10, Wonderful, (31)
"Check in was easy, beds are comfortable. I’m a big and tall guy, so only qualm I had was the small toilet, and low shower head. Aside from those, great stay!"
Upstairs on Main
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
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. "
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
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
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Super comfortable Mountain Decor

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

10.0 out of 10, Exceptional, (22)
"We loved our stay. The rental was as described. Jiminy Peak is great and everything is within walking distance. We had a great time !!!"
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
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 720
AED 1,258 total
includes taxes & fees
2 Jan - 3 January 2025
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Renovated Downtown 1bedroom
Living area

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (21)
"Location, location, location. Great use of space in this nicely decorated, conveniently located apt. Steps away from restaurants and shopping. 7 minutes from Kripalu. Great communication from owner. Looking forward to next stay."
Renovated Downtown 1bedroom
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Living area

Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great location! The apartment was brand new. Well decorated and clean. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
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
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
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

10.0 out of 10, Exceptional, (5)
"Condo was conveniently located at the base of the mountain. Had everything you would need for a quick weekend getaway. Owner was available for any questions."
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
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, (1750)
"Nice and quiet family get a way"
The price is AED 689
AED 792 total
includes taxes & fees
1 Jan - 2 January 2025
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 694
AED 762 total
includes taxes & fees
1 Jan - 2 January 2025
Jiminy Peak Mountain Resort
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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: Cozy Rustic Apt in 18th c Berkshire Farmhouse: Situated in Lanesborough, 3.9 mi/6.3 km from the heart of Cheshire. Includes fireplaces and sofa beds. Lovely two bedroom river-view rental unit: Located 11.5 mi/18.5 km away in Williamstown. Amenities include sofa beds. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: It’s situated in Lee, 18.1 mi/29.1 km away. Includes private patios and fireplaces. Charming Apt in 18th c Berkshire Farmhouse: 3.9 mi/6.3 km away in Lanesborough. Amenities include fireplaces.
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.