Photo by Ed Gaffny

Search Apartments in Cheshire

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

Vacation Rental Home in the Berkshires!
Outdoor dining

Vacation Rental Home in the Berkshires!

3.0 star property
Vacation Rental Home in the Berkshires!
51 Seymour St
35-inch LCD TV with digital channels, Netflix, Hulu

51 Seymour St

3.5 star property
51 Seymour St
Family-friendly Hancock Home: Walk to Slopes!
Apartment (4 Bedrooms) | Interior

Family-friendly Hancock Home: Walk to Slopes!

3.0 star property
Family-friendly Hancock Home: Walk to Slopes!
Berkshires Getaway < 1 Mi Skiing & Hiking!
Apartment (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Berkshires Getaway < 1 Mi Skiing & Hiking!

3.0 star property
Berkshires Getaway < 1 Mi Skiing & Hiking!
Downtown Pittsfield Vacation Rental Near Hiking!
Exterior

Downtown Pittsfield Vacation Rental Near Hiking!

3.0 star property
Downtown Pittsfield Vacation Rental Near Hiking!
Berkshires Apt w/ Deck & Mtn Views!
Interior

Berkshires Apt w/ Deck & Mtn Views!

3.0 star property
Berkshires Apt w/ Deck & Mtn Views!
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
Indoor pool, outdoor pool, pool umbrellas

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 NT$6,134
NT$7,056 total
includes taxes & fees
Jan 5 - 2025/1/6
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 NT$6,126
NT$6,720 total
includes taxes & fees
Jan 21 - 2025/1/22
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 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.