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Compare 95 Apartments in Cheshire with updated reviews, rates, and availability.

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (27)
"Clean, comfortable and great location."
51 Church Street, Lenox MA - One Bedroom Unit

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

10.0 out of 10, Exceptional, (2)
"This apartment is roomy and fully appointed. Because of some physical issues we were unable to use the queen bed...it was too high. However, the twin beds were very comfy. The location is just right. So close to the Mohawk Trail, VT border and all the wonderful businesses that revolve around art. Our visits with family and friends were made even better because of our carefree accommodations! Thank you...SandyPeggi & Rick"
The price is AED 496
AED 853 total
includes taxes & fees
31 May - 1 Jun
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.

Park Street Penthouse Apartment

9.0 out of 10, Wonderful, (2)
"We stayed in this beautiful penthouse for an overnight get away- we both walked in and were just in love. The high ceilings and tons of windows made it so open feeling. Stunning place!"
The price is AED 716
AED 1,251 total
includes taxes & fees
21 May - 22 May
Park Street Penthouse Apartment

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"Very clean and nicely decorated apartment in center of town. Great location. Really enjoyed our vacation."
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

The Studio mini home away from home in the Berkshires

9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
The Studio mini home away from home in the Berkshires

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (31)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is AED 496
AED 763 total
includes taxes & fees
26 May - 27 May
Charming Apt in 18th c Berkshire Farmhouse

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.6 out of 10, Exceptional, (26)
"My family had a great ski weekend at Howard’s place. Everything was as described and the location could not be beat! Howard was an excellent host - super communicative and very prompt in responding to the few questions we had. We would absolutely stay here again. "
The price is AED 646
AED 1,284 total
includes taxes & fees
21 May - 22 May
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Downtown | Waterfront | Walk to Shops

10.0 out of 10, Exceptional, (4)
"Beautiful property and wonderful hosts. Terrific location."
The price is AED 477
AED 1,012 total
includes taxes & fees
2 Jun - 3 Jun
Downtown | Waterfront | Walk to Shops

Upstairs on Main with private bathroom

9.2 out of 10, Wonderful, (32)
"We enjoyed our stay in this great place! cute little upstairs apartment with a great use of space and perfect for getting around the area. We got the benefit of a beautiful snow storm too (and the walk and parking area were shoveled when we woke up which was nice!) thanks again."
Upstairs on Main with private bathroom

2-Bdr Apt In Town, By the Water

9.6 out of 10, Exceptional, (4)
"The apartment was clean, bright and quiet. Comfortable beds, and well equipped kitchen. About 3 minute walk to shops on spring street and a nice spot out back by the Green river. Perfect spot for a visit to Williamstown! "
The price is AED 441
AED 991 total
includes taxes & fees
26 May - 27 May
2-Bdr Apt In Town, By the Water

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
The price is AED 551
AED 804 total
includes taxes & fees
31 May - 1 Jun
Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great place! Location was ideal, close to everything. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

Private Suite with a Sweet View. Spacious, close to town, dog friendly

10.0 out of 10, Exceptional, (31)
"Great space. Lots of room for us and very clean and comfortable."
Private Suite with a Sweet View. Spacious, close to town, dog friendly

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

9.8 out of 10, Exceptional, (18)
"Great place to spend the new years holiday! Perfect location for skiing!"
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

10.0 out of 10, Exceptional, (3)
"Condo in great location for skiing and really in good shape. Nicely decorated. Kids loved the moose toy. Kitchen had everything we needed. Perfect winter break for us. "
The price is AED 459
AED 952 total
includes taxes & fees
21 May - 22 May
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

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

1500 sqft private entrance with beautiful views of the Berkshire Mountains

10.0 out of 10, Exceptional, (41)
"Perfect get away, convenient to everything."
1500 sqft private entrance with beautiful views of the Berkshire Mountains

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

9.0 out of 10, Wonderful, (2)
"Loved our short stay! Very clean, well maintained, and super cozy. Communication was very prompt and pleasant. Would definitely stay again! "
The price is AED 624
AED 1,169 total
includes taxes & fees
12 Jun - 13 Jun
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Ground floor 2/3 bed apartment

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great property and location for a visit to Shelburne Falls. "
The price is AED 668
AED 1,043 total
includes taxes & fees
21 May - 22 May
Ground floor 2/3 bed apartment

Vacation Rental Home in the Berkshires!

3.0 star property
Vacation Rental Home in the Berkshires!
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

3.0 star property
8.6 out of 10, Excellent, (1808)
"The property was clean and the staff very accommodated."
The price is AED 390
AED 476 total
includes taxes & fees
21 May - 22 May
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (929)
"Out dated not many resort like options "
The price is AED 493
AED 550 total
includes taxes & fees
21 May - 22 May
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow
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: Charming Apt in 18th c Berkshire Farmhouse: Located in Lanesborough, 3.9 mi/6.3 km from the heart of Cheshire. Includes fireplaces. Access to onsite laundry facilities is available on site. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 18.1 mi/29.1 km away in Lee. Private patios and fireplaces are included. Access to onsite laundry facilities is available on site. Bright Boho Apt in 18th c Berkshire Farmhouse: It’s situated in Lanesborough, 3.9 mi/6.2 km away. Includes sofa beds. 51 Church Street, Lenox MA - One Bedroom Unit: 15.4 mi/24.7 km away in Lenox. FARM-TO-TABLE eating, good hot tub soak, S’mores around fire pit, seasonal POOL!: Located in Pownal, 16.3 mi/26.2 km from Cheshire. Includes a private pool, free WiFi, and private patios. Onsite laundry facilities and an outdoor pool are 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.