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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 91 Apartments in Cheshire with updated reviews, rates, and availability.

51 Church Street, Lenox MA - One Bedroom Unit
Fridge, microwave, oven, stovetop

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (27)
"The property was pristine, spacious, and perfectly located. Everything was convenient and in order; parking was easy.Will plan to stay again."
51 Church Street, Lenox MA - One Bedroom Unit
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.
Fridge, microwave, oven, stovetop

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 841 total
includes taxes & fees
30 Apr - 1 May
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.
Park Street Penthouse Apartment
Game room

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 606
AED 1,128 total
includes taxes & fees
2 Apr - 3 Apr
Park Street Penthouse Apartment
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
The Studio mini home away from home in the Berkshires
Outdoor dining

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
Miscellaneous

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 496
AED 763 total
includes taxes & fees
2 Apr - 3 Apr
Charming Apt in 18th c Berkshire Farmhouse
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (25)
"Super convenient - just steps to the lift, right in the middle of resort. Can walk to lifts, the lodge ski school and restaurants. Condo has everything you need for for fun family weekend!Teen boys had lots of freedom and could come And go for night skiing on their own!Def renting from Howie again!! "
The price is AED 577
AED 1,171 total
includes taxes & fees
2 Apr - 3 Apr
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Downtown | Waterfront | Walk to Shops
Property grounds

Downtown | Waterfront | Walk to Shops

10.0 out of 10, Exceptional, (2)
"My two friends and I stayed for the night after visiting Mass MoCa. The apartment was lovely, clean and conveniently located. The kitchen was lovely; we enjoyed the layout and the counter space. My friend and I grabbed a nice dinner across the street. It’s a great stay! "
The price is AED 477
AED 1,016 total
includes taxes & fees
2 Apr - 3 Apr
Downtown | Waterfront | Walk to Shops
Upstairs on Main with private bathroom
Property grounds

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
Outdoor dining

2-Bdr Apt In Town, By the Water

9.4 out of 10, Exceptional, (3)
"Very nice upstairs 2Br apt. Very clean, nice amount of space, and beautiful backyard view on the river. The stairs to get to the apt are very steep and the traffic can be busy /loud in the mornings. But nice place overall. "
The price is AED 441
AED 983 total
includes taxes & fees
15 Apr - 16 Apr
2-Bdr Apt In Town, By the Water
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Living area

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
The price is AED 551
AED 812 total
includes taxes & fees
2 Apr - 3 Apr
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Exterior

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (8)
"The place was very comfortable and in a great location. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Private Suite with a Sweet View. Spacious, close to town, dog friendly
Exterior

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

10.0 out of 10, Exceptional, (30)
"Great property with great view, cute suite with everything we needed for a short stay while getting our daughter settled back in at Amherst College. Enjoyed a nice dinner nearby at Blue Rock Shelburne Falls, a little shopping and coffee at Mocha mayas and Shelburne Falls Coffee Roasters. My husband did a little fly fishing just off the property in the Deerfield River. Thank you!"
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
Exterior

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

9.8 out of 10, Exceptional, (18)
"Planned on a Thursday. Arrived late Friday, skied Sat, home early Sun. All fell into place quickly and without much "research". Turned out to be an amazing trip."
The price is AED 382
AED 844 total
includes taxes & fees
3 Apr - 4 Apr
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
Property grounds

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 382
AED 844 total
includes taxes & fees
3 Apr - 4 Apr
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
Exterior

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 AED 382
AED 844 total
includes taxes & fees
3 Apr - 4 Apr
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
Golf

1500 sqft private entrance with beautiful views of the Berkshire Mountains

10.0 out of 10, Exceptional, (41)
"My husband and I stayed at this clean, spacious, and well-equipped apartment adjacent to the hosts' home for three nights to visit nearby attractions in Lenox, Pittsfield, Great Barrington, and Stockbridge. It was a wonderful property and the hosts couldn't have been nicer. We especially loved the gift basket prepared with some of their favorite area treats. Communication about the check-in/check-out process was simple. FYI for future travelers: there are no bathroom toiletries provided so...
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
Exterior

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

9.0 out of 10, Wonderful, (2)
"Great stay with a great view of the slopes. The owner was in touch with us the whole time. He was great."
The price is AED 382
AED 844 total
includes taxes & fees
3 Apr - 4 Apr
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Charming Ground-Floor 2/3 bedroom apartment in Shelburne Falls, MA
Living area

Charming Ground-Floor 2/3 bedroom apartment in Shelburne Falls, MA

2.0 star property
The price is AED 727
AED 1,182 total
includes taxes & fees
2 Apr - 3 Apr
Charming Ground-Floor 2/3 bedroom apartment in Shelburne Falls, MA
Vacation Rental Home in the Berkshires!
Interior

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
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"The location to jimney peak was great."
The price is AED 437
AED 520 total
includes taxes & fees
14 Apr - 15 Apr
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, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 540 total
includes taxes & fees
2 Apr - 3 Apr
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (240)
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "
The price is AED 551
AED 837 total
includes taxes & fees
2 Apr - 3 Apr
Berkshire Village Carriage House - Super Private!!
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: Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Situated in Lee, 18.1 mi/29.1 km from the heart of Cheshire. Includes private patios and fireplaces. 51 Church Street, Lenox MA - One Bedroom Unit: Located 15.4 mi/24.7 km away in Lenox. The Studio mini home away from home in the Berkshires: It’s situated in Lee, 18.1 mi/29.1 km away. Includes private patios. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor: Located 6.5 mi/10.5 km away in Hancock. Amenities include sofa beds. A fitness center and an indoor pool are on site. Park Street Penthouse Apartment: It’s located in Adams, 4.7 mi/7.6 km from Cheshire. Includes sofa beds.
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.