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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

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
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 298
AED 580 total
includes taxes & fees
17 Feb - 18 Feb
Getaway Near Mass MoCA, Great Hiking, Scenic Views
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, (12 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 1,033 total
includes taxes & fees
1 Mar - 2 Mar
2-Bdr Apt In Town, By the Water
Beach

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very Good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is AED 444
AED 923 total
includes taxes & fees
19 Feb - 20 Feb
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
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
16 Feb - 17 Feb
2 Twin beds on 1st floor with En-suite bathroom.
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 991 total
includes taxes & fees
15 Feb - 16 Feb
New Studio 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 1,030 total
includes taxes & fees
16 Feb - 17 Feb
Penthouse Apartment on Park Street
Pool

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (30 reviews)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
United States
Maura S.
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Indoor pool

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.6 out of 10, Exceptional, (20 reviews)
"We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip."
United States
Allison V.
The price is AED 984
AED 1,629 total
includes taxes & fees
16 Feb - 17 Feb
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
TV, fireplace, DVD player, offices

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Excellent instructions by the owner for the check in process, which was easy. The room was beautiful and very clean, and exactly as advertised. We would absolutely recommend and stay again!!"
United States
Chad J.
The price is AED 459
AED 1,005 total
includes taxes & fees
4 Mar - 5 Mar
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
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 1,778
AED 2,941 total
includes taxes & fees
22 Feb - 23 Feb
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Property grounds

2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
The price is AED 472
AED 981 total
includes taxes & fees
19 Feb - 20 Feb
2 Bed Berkshire Getaway @ Stephentown Hotel
Gift shop

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

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is AED 1,216
AED 1,924 total
includes taxes & fees
20 Feb - 21 Feb
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
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
16 Feb - 17 Feb
Rose wisteria 4 guests 2 bedrooms-full+queen beds
1 bedroom, iron/ironing board, WiFi, bed sheets

Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere

Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere
Hancock
10.0 out of 10, Exceptional, (1 review)
"Great!"
United States
Susan M.
The price is AED 882
AED 1,489 total
includes taxes & fees
17 Feb - 18 Feb
Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere
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 Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Everything! :)"
Joanie 5-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

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: Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located in Lee, 18.1 mi/29.1 km from the heart of Cheshire. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton: Located 6.1 mi/9.9 km away in Dalton. Free WiFi, separate dining areas, and Smart TVs are included. Access to onsite laundry facilities is available on site. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4: It's located in Hancock, 6.5 mi/10.5 km away. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake: Located 21.2 mi/34.1 km away in Whitingham. Private balconies, fireplaces, and Smart TVs are included. Free breakfast and onsite laundry facilities are on site. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor: Located in Hancock, 6.5 mi/10.5 km from Cheshire. Includes sofa beds. A fitness center and an indoor 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.

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