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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Cheshire apartments

Exterior

2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is AED 338
AED 661 total
includes taxes & fees
3 Mar - 4 Mar
2 Twin beds on 1st floor with En-suite bathroom.
Exterior

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (28 reviews)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
The price is AED 248
AED 525 total
includes taxes & fees
10 Feb - 11 Feb
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Exterior

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is AED 570
AED 1,039 total
includes taxes & fees
10 Feb - 11 Feb
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Pool

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is AED 503
AED 1,013 total
includes taxes & fees
10 Feb - 11 Feb
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Outdoor dining

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (10 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is AED 441
AED 975 total
includes taxes & fees
10 Feb - 11 Feb
New Studio In Town, By the Water
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is AED 477
AED 1,062 total
includes taxes & fees
18 Feb - 19 Feb
Downtown | Waterfront | Walk to Shops
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.6 out of 10, Exceptional, (11 reviews)
"Clean, close to town, very convenient. On a busy road, so just be aware of that. But overall a good place to stay. "
United States
Brian L.
The price is AED 441
AED 1,025 total
includes taxes & fees
1 Mar - 2 Mar
2-Bdr Apt In Town, By the Water
Living area

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (14 reviews)
"Clean property, easy check in, and the owner was super communicative. "
United States
Amanda W.
The price is AED 533
AED 1,034 total
includes taxes & fees
10 Feb - 11 Feb
Penthouse Apartment on Park Street
Property grounds

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is AED 503
AED 1,013 total
includes taxes & fees
10 Feb - 11 Feb
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Beach

Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (3 reviews)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is AED 401
AED 842 total
includes taxes & fees
10 Feb - 11 Feb
Berkshires Apartment at the Stephentown Hotel
Fridge, microwave, stovetop, dishwasher

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
10.0 out of 10, Exceptional, (2 reviews)
"as advertised."
United States
Joshua G.
The price is AED 1,600
AED 2,726 total
includes taxes & fees
10 Feb - 11 Feb
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Outdoor dining

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"Great room decorations, travel with two kids they have a great time playing video games"
United States
Andres
The price is AED 503
AED 1,013 total
includes taxes & fees
10 Feb - 11 Feb
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Gift shop

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is AED 503
AED 1,013 total
includes taxes & fees
10 Feb - 11 Feb
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Pool

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (16 reviews)
"Nice Place"
United States
Tom C.
The price is AED 503
AED 1,013 total
includes taxes & fees
10 Feb - 11 Feb
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Indoor pool

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

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
The price is AED 503
AED 1,013 total
includes taxes & fees
10 Feb - 11 Feb
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Pool

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (34 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is AED 775
AED 1,456 total
includes taxes & fees
10 Feb - 11 Feb
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (1 review)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
United States
Antonio S.
The price is AED 503
AED 1,013 total
includes taxes & fees
10 Feb - 11 Feb
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Exterior

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

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (10 reviews)
"Room was perfect location for skiing. Able to see slopes and a few of the chairlifts from room. Beds were super comfortable. Parking was close by and in private area which helped avoid parking in huge resort parking lot. Owner was very responsive."
United States
Charles
The price is AED 503
AED 1,013 total
includes taxes & fees
10 Feb - 11 Feb
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Indoor pool, a heated pool

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Great location. Very nice vacation. Would def go again. "
United States
Elizabeth M.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Feb - 12 Feb
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A heated pool

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

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Hancock
9.6 out of 10, Exceptional, (4 reviews)
"My family loved our stay here at Jiminy! You can’t beat the ski in and ski out feature, in addition to dining and several amenities all within the resort. Howard was an attentive and communicative host, ensuring we had everything our needed to have the best stay possible. We will definitely be returning!"
United States
katie s.
The price is AED 503
AED 1,013 total
includes taxes & fees
10 Feb - 11 Feb
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"The staff was wonderful "
Linda 2-night trip
Posted 14 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

What's it like to stay at an apartment in Cheshire?
You'll find 6 accommodations in Cheshire. Though there aren't many apartments, we can help you find similar accommodations. 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: Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton: Located in Dalton, 6.1 mi/9.9 km from the heart of Cheshire. Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- 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. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4: It's located in Hancock, 6.5 mi/10.5 km away. 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. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake: Located in Whitingham, 21.2 mi/34.1 km from Cheshire. Includes private balconies, fireplaces, and Smart TVs. Free breakfast and onsite laundry facilities 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.

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