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11 Jul - 13 Jul
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18 Jul - 20 Jul
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1 Aug - 3 Aug
In two months
29 Aug - 31 Aug

Apartments in Cheshire

Charming 1-bedroom apartment in wonderful Lenox Dale
Exterior

Charming 1-bedroom apartment in wonderful Lenox Dale

10.0 out of 10, Exceptional, (2)
"What a wonderful property! Ellen had it completely fitted out so you could live there long term if you wanted! It was also near everything we needed. Delightful!"
Charming 1-bedroom apartment in wonderful Lenox Dale
Charming Apt in 18th c Berkshire Farmhouse
1 bedroom, WiFi, bed sheets

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (33)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is SAR 506
SAR 774 total
includes taxes & fees
6 Jul - 7 Jul
Charming Apt in 18th c Berkshire Farmhouse
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
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, (81)
"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!
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Fridge, microwave, oven, stovetop

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

2.0 star property
9.6 out of 10, Exceptional, (4)
"My husband and I and our little dog had an amazing stay in Dalton. The space was clean, perfectly decorated and comfortable! We only stayed a few days and wanted to stay so much longer! Coffee for the humans and frog toys and treats for Sully! Very convenient to all the Berkshires has to offer. Communication with the owner was prompt and always helpful!! Highly recommend and hope to return. "
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Downtown | Waterfront | Walk to Shops
Outdoor dining

Downtown | Waterfront | Walk to Shops

10.0 out of 10, Exceptional, (4)
"Beautiful property and wonderful hosts. Terrific location."
The price is SAR 488
SAR 1,037 total
includes taxes & fees
7 Jul - 8 Jul
Downtown | Waterfront | Walk to Shops
6 Mi to Tanglewood: Peaceful Berkshire Apt!
Living area

6 Mi to Tanglewood: Peaceful Berkshire Apt!

6 Mi to Tanglewood: Peaceful Berkshire Apt!
Downtown Gateway to the Berkshires. Walk to Everything.
Exterior detail

Downtown Gateway to the Berkshires. Walk to Everything.

2.0 star property
8.0 out of 10, Very Good, (1)
"This cute and cozy apartment was in an excellent location. We were the first guest to stay here and we had a few concerns: the chairs in the kitchen were broken as was a door frame. The command hooks fell off the several times. There was no place to hang clothes and shelves which held the dishes were dirty and dusty as well as appliances. Some coffee and Kleenex would have a nice. The place has the potential to be amazing with a little more attention to details. We have stayed in many, many...
Downtown Gateway to the Berkshires. Walk to Everything.
Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.6 out of 10, Exceptional, (5)
"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 SAR 506
SAR 1,005 total
includes taxes & fees
6 Jul - 7 Jul
Park Street Penthouse Apartment
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Exterior

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

9.8 out of 10, Exceptional, (7)
"This property was awesome for our family! Quick walk to the Mountain and all the shops!!! Great family spot!!"
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Charming Apartment In Berkshire Victorian Home
Interior

Charming Apartment In Berkshire Victorian Home

7.8 out of 10, Good, (7)
"This adorable place is central to Pittsfield and made it really easy for my daughter and I go get where we needed to be. It’s a clean, great space. We’ll definitely be back!"
Charming Apartment In Berkshire Victorian Home
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 SAR 525
SAR 1,110 total
includes taxes & fees
16 Jul - 17 Jul
2-Bdr Apt In Town, By the Water
Bright Boho Apt in 18th c Berkshire Farmhouse
Property grounds

Bright Boho Apt in 18th c Berkshire Farmhouse

9.0 out of 10, Wonderful, (22)
"Really enjoyed our stay"
The price is SAR 544
SAR 816 total
includes taxes & fees
13 Jul - 14 Jul
Bright Boho Apt in 18th c Berkshire Farmhouse
Gateway to the Berkshires - Renovated downtown apartment
Exterior

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (8)
"Emmy is a great hostess. The apartment is nicely appointed and in a great location to restaurants and shops and attractions in the Berkshires. "
Gateway to the Berkshires - Renovated downtown apartment
Heart of Lenox!! - renovated downtown apartment
Exterior

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (69)
"Beautiful property in a perfect location for a girls ski weekend getaway! "
Heart of Lenox!! - renovated downtown apartment
Ground floor 2/3 bed apartment
Property grounds

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
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Exterior

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
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! "
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Exterior

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

10.0 out of 10, Exceptional, (8)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.6 out of 10, Exceptional, (26)
"We really enjoyed our stay it was a very nice place for a family."
The price is SAR 596
SAR 1,223 total
includes taxes & fees
7 Jul - 8 Jul
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
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. 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. 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.
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.