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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

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

Charming Apt in 18th c Berkshire Farmhouse
Miscellaneous

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
3 Jun - 4 Jun
Charming Apt in 18th c Berkshire Farmhouse
Bright Boho Apt in 18th c Berkshire Farmhouse
Miscellaneous

Bright Boho Apt in 18th c Berkshire Farmhouse

9.0 out of 10, Wonderful, (22)
"Really enjoyed our stay"
The price is AED 533
AED 808 total
includes taxes & fees
3 Jun - 4 Jun
Bright Boho Apt in 18th c Berkshire Farmhouse
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, (30)
"Clean, comfortable and great location."
51 Church Street, Lenox MA - One Bedroom Unit
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

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

9.4 out of 10, Exceptional, (61)
"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
2-Bdr Apt In Town, By the Water
Outdoor dining

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
18 Jun - 19 Jun
2-Bdr Apt In Town, By the Water
Downtown | Waterfront | Walk to Shops
Property grounds

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 1,016 total
includes taxes & fees
3 Jun - 4 Jun
Downtown | Waterfront | Walk to Shops
Main Street Delight 1bedroom
TV

Main Street Delight 1bedroom

10.0 out of 10, Exceptional, (22)
"Excellent location. Just a short walk to restaurants and shops. Updated amenities and well-stocked kitchen."
Main Street Delight 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, (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
Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.4 out of 10, Exceptional, (3)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
The price is AED 716
AED 1,251 total
includes taxes & fees
3 Jun - 4 Jun
Park Street Penthouse Apartment
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)
"Perfect get away, convenient to everything."
1500 sqft private entrance with beautiful views of the Berkshire Mountains
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Property grounds

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

9.8 out of 10, Exceptional, (7)
"Everything was wonderful…"
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
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 849 total
includes taxes & fees
11 Jun - 12 Jun
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.
Vacation Rental Home in the Berkshires!
Apartment (0 Bedroom) | Interior

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
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. "
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Ground floor 2/3 bed apartment
Living area

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. "
Ground floor 2/3 bed apartment
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Outdoor spa tub

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

10.0 out of 10, Exceptional, (7)
"We had a wonderful 3 day weekend! Perfect location for families."
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Renovated Downtown 1bedroom
Stovetop, dishwasher

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
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)
"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 1,161 total
includes taxes & fees
12 Jun - 13 Jun
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Smart TV, fireplace, DVD player, music library

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

9.4 out of 10, Exceptional, (80)
"Nice place, just what we were looking for to stay the weekend. "
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Miscellaneous

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (62)
"The room itself was well kept, clean, and had everything we needed!Located right near a coffee house / country store, down the road from Jiminy Peak, and a short drive to some great hiking spots- this is all you need for a weekend getaway!"
The price is AED 496
AED 763 total
includes taxes & fees
3 Jun - 4 Jun
Cozy Rustic Apt in 18th c Berkshire Farmhouse
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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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. Bright Boho Apt in 18th c Berkshire Farmhouse: Located 3.9 mi/6.2 km away in Lanesborough. Amenities include sofa beds. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located in Lee, 18.1 mi/29.1 km away. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. FARM-TO-TABLE eating, good hot tub soak, S’mores around fire pit, seasonal POOL!: Located 16.3 mi/26.2 km away in Pownal. A private pool, free WiFi, and private patios are included. Onsite laundry facilities and an outdoor pool are on site. 51 Church Street, Lenox MA - One Bedroom Unit: It’s situated in Lenox, 15.4 mi/24.7 km from Cheshire.
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.