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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct

Apartments in Cheshire

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, (34)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is SAR 507
SAR 779 total
includes taxes & fees
21 Aug - 22 Aug
Charming Apt in 18th c Berkshire Farmhouse
Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.4 out of 10, Exceptional, (9)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
The price is SAR 507
SAR 1,006 total
includes taxes & fees
21 Aug - 22 Aug
Park Street Penthouse Apartment
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, (82)
"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!
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, (63)
"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
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.
Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
Living area

Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge

9.0 out of 10, Wonderful, (2)
"The apartment is in downtown Stockbridge. We were there to aid our son and his fiancee who are traversing the Appalachia Trail. The location was perfect for us. The apartment is complete new and immaculate. It was very comfortable for the four of us. The only reason that the overall review is four not five stars is that the dryer wasn't working and the kitchen had absolutely now supplies or an ice tray. The dryer not working could have been a disaster for us as we needed to clean our son's...
Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
2-Bdr Apt In Town, By the Water
Outdoor dining

2-Bdr Apt In Town, By the Water

9.8 out of 10, Exceptional, (6)
"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 488
SAR 1,059 total
includes taxes & fees
9 Sep - 10 Sep
2-Bdr Apt In Town, By the Water
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
9.8 out of 10, Exceptional, (9)
"Clean and well stock"
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
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, (32)
"Great space. Lots of room for us and very clean and comfortable."
Private Suite with a Sweet View. Spacious, close to town, dog friendly
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
Ground floor 2/3 bed apartment
Property grounds

Ground floor 2/3 bed apartment

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great property and location for a visit to Shelburne Falls. "
The price is SAR 724
SAR 1,373 total
includes taxes & fees
27 Aug - 28 Aug
Ground floor 2/3 bed 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
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 825 total
includes taxes & fees
25 Aug - 26 Aug
Bright Boho Apt in 18th c Berkshire Farmhouse
Vacation Rental Home in the Berkshires!
Outdoor dining

Vacation Rental Home in the Berkshires!

9.8 out of 10, Exceptional, (17)
"Lovely cottage with beautiful views"
Vacation Rental Home in the Berkshires!
Heart of Lenox!! - renovated downtown apartment
Exterior

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (71)
"Beautiful property in a perfect location for a girls ski weekend getaway! "
Heart of Lenox!! - renovated downtown apartment
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (62)
"Great value, so much better than all the touristy motels in the area!"
The price is SAR 507
SAR 779 total
includes taxes & fees
21 Aug - 22 Aug
Cozy Rustic Apt in 18th c Berkshire Farmhouse
The Penthouse, Downtown Lenox by Evergreen Home
Fridge, microwave, oven, stovetop

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (8)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home
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
Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in/out!
Interior

Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in/out!

Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in/out!
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
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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Top Cheshire Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Clean"
Higeong 2-night trip
Posted 2 days ago
The Williams Inn

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: 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 the heart of Cheshire. Includes a private pool, free WiFi, and private patios. Onsite laundry facilities and an outdoor pool are on site. Charming Apt in 18th c Berkshire Farmhouse: Located 3.9 mi/6.3 km away in Lanesborough. Amenities include fireplaces. Access to onsite laundry facilities is available on site. 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. Park Street Penthouse Apartment: Located 4.7 mi/7.6 km away in Adams. Amenities include sofa beds. Access to onsite laundry facilities is available 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.