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Check prices for these dates

Next weekend
14 Saf. - 16 Saf.
In two weeks
21 Saf. - 23 Saf.
In one month
7 Rab. I - 9 Rab. I
In two months
4 Rab. II - 6 Rab. II

Compare 77 Apartments in Cheshire with updated reviews, rates, and availability.

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Fully Updated Bedroom w Super Comfy King Bed

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

10.0 out of 10, Exceptional, (1)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
The price is SAR 589
SAR 1,101 total
includes taxes & fees
5 Feb - 6 Feb
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
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."
The price is SAR 589
SAR 1,101 total
includes taxes & fees
5 Feb - 6 Feb
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Comfy Cabin Decor with Ultra-Premium Bedding

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

10.0 out of 10, Exceptional, (4)
"Perfect place to stay for a quick ski trip. Host was super helpful & accommodating. Suite was comfortable & well-equipped. We’ll be back "
The price is SAR 589
SAR 1,101 total
includes taxes & fees
5 Feb - 6 Feb
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
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, (5)
"Perfect location. Walking distance. Brand new apartment. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
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, (30)
"Perfect 1 bedroom, ski in ski off , updated unit with great amenities! Owner super responsive and accommodating. Will definitely be back "
The price is SAR 589
SAR 1,101 total
includes taxes & fees
5 Feb - 6 Feb
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
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, (7)
"This is the second year we had our girls weekend at the Penthouse and it did not disappoint. The place is updated, very clean, and in a great location! Only suggestion would to get a nice big sectional couch! We had 8 people and not enough comfy seating. But beautiful apartment!! "
The Penthouse, Downtown Lenox by Evergreen Home
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
9.0 out of 10, Wonderful, (2)
"Our stay was excellent overall! We really admired the tidiness of the property. The ski trails were hit to. The only thing that brought this review down was that the T.V.’s in our room were not working but the stay was pretty good!"
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
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."
Lovely two bedroom river-view rental unit
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, (23)
"Everything was great. Very clean unit and it def is a ski in/out. Plenty of space in bedrooms. Howard is easy to communicate with and a great host. Truly a gem in jimminy peak. "
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.
Living area

Serene 2-bedroom apartment in North Adams.Plenty of off street parking.

10.0 out of 10, Exceptional, (1)
"Hi-- my son and I were in town for a concert at MASS MOCA. I was having trouble getting into the app on my phone so couldn't pull up the entry code and an unexpected snowstorm sprang up when we were 1-1/2 hours away. Our host was very helpful and gave me instructions over the phone and left the lights on for us so we could find the house. She was wonderful and so was the property. 5 minutes by car to the museum and downtown. Highly recommended!"
The price is SAR 506
SAR 876 total
includes taxes & fees
6 Feb - 7 Feb
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.
Vacation Rental Home in the Berkshires!
Williamstown Vacation Rental | Studio | 1BA | Stairs Required | 1,000 Sq Ft

Vacation Rental Home in the Berkshires!

9.8 out of 10, Exceptional, (12)
"This is a very special place to stay. It is comfortable and cozy. The mountain scenery is fantastic, uplifting and quite beautiful.We will be back again when we visit our family in Williamstown. The owner is very welcomingand responds to our texts in a timely manner."
Vacation Rental Home in the Berkshires!
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Snuggle up with Yetis in the King master Suite

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

9.8 out of 10, Exceptional, (17)
"The condo was clean and well located for easy access to the mountain. We were there for tri-state races and having easy acass to the mountain was exactly what we needed for a fun weekend. We would stay here again."
The price is SAR 589
SAR 1,101 total
includes taxes & fees
5 Feb - 6 Feb
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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 SAR 589
SAR 1,101 total
includes taxes & fees
5 Feb - 6 Feb
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, (22)
"We’ve always had a great experience with Downtown Upstairs in Lenox and this was no exception. Easy access to the downtown stores and restaurants with the comfort of a nice, clean, well furnished apartment. "
Renovated Downtown 1bedroom
Vacation Rental Home in the Berkshires!
Living area

Vacation Rental Home in the Berkshires!

3.0 star property
Vacation Rental Home in the Berkshires!
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, (60)
"The property was fine for our purposes of visiting family. If we needed to cook, it would have been quite difficult, though not totally impossible. The furniture was comfortable and the rooms, except the kitchen, had plenty of space. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Lovely bright apartment in pastoral shaker barn
Welcome to Dublinshire Farm, apartment one!

Lovely bright apartment in pastoral shaker barn

10.0 out of 10, Exceptional, (2)
"We traveled from Arizona for a class reunion and stayed in apartment. The property was clean and well appointed. We were able to host a dinner with four family members we had not seen in years! Another highlight was sitting outside by the fire pit in the evening. The property host, Michelle, provided excellent check in instructions and answered any questions very promptly. This property worked out very well for us, but if you have an issue with stairs you might want to check out the other...
Lovely bright apartment in pastoral shaker barn
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

9.0 out of 10, Wonderful, (10)
"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 SAR 589
SAR 1,101 total
includes taxes & fees
5 Feb - 6 Feb
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
51 Church Street, Lenox MA - One Bedroom Unit
Living area

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (24)
"Lovely apartment in a great location "
51 Church Street, Lenox MA - One Bedroom Unit
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
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, (1759)
"Great place "
The price is SAR 563
SAR 655 total
includes taxes & fees
6 Feb - 7 Feb
Vacation Village in the Berkshires
The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow by Capital Vacations
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (924)
"Staff was exceptionally helpful and friendly."
The price is SAR 709
SAR 778 total
includes taxes & fees
5 Feb - 6 Feb
Jiminy Peak Mountain Resort
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: 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor: Located in Hancock, 6.5 mi/10.5 km from the heart of Cheshire. Includes sofa beds. A fitness center and an indoor pool are on site. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor: Located 6.5 mi/10.5 km away in Hancock. Amenities include sofa beds. A fitness center and a spa tub are on site. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone: Located in Hancock, 6.5 mi/10.5 km away. Includes sofa beds. A fitness center and an indoor pool are on site. Charming Apt in 18th c Berkshire Farmhouse: 3.9 mi/6.3 km away in Lanesborough. Amenities include fireplaces. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: It’s located in Lee, 18.1 mi/29.1 km from Cheshire. Includes private patios and 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.