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Apartments in Cheshire

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 263
AED 576 total
includes taxes & fees
25 Nov - 26 Nov
2 Twin beds on 1st floor with En-suite bathroom.
Exterior detail
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford
10.0 out of 10, Exceptional, (27)
"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 251
AED 528 total
includes taxes & fees
20 Nov - 21 Nov
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Great value, so much better than all the touristy motels in the area!"
United States
Chris G.
The price is AED 496
AED 763 total
includes taxes & fees
20 Nov - 21 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Exterior
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)
"We had a wonderful stay in our fun, pirate themed suite. Which is really what caught our attention in making our reservation. It was so thoughtfully decorated, and suited the theme, while still being a comfortable place to enjoy being in. Everything was in wonderful condition, and had all the amenities we needed. Our host, Howie, was incredibly attentive, personable, and made sure we were taken care of. I was very disorganized, and he went out of his way to get me all the information we needed...
United States
Karen
The price is AED 386
AED 866 total
includes taxes & fees
20 Nov - 21 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
1 bedroom, iron/ironing board, bed sheets
Penthouse Apartment on Park Street

Penthouse Apartment on Park Street

2.0 star property
Adams
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is AED 426
AED 899 total
includes taxes & fees
20 Nov - 21 Nov
Penthouse Apartment on Park Street
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, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is AED 404
AED 886 total
includes taxes & fees
20 Nov - 21 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
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)
"Effortless process! We arrived and felt at home immediately. Could not have been happier with our experience."
United States
Staci A.
The price is AED 441
AED 991 total
includes taxes & fees
20 Nov - 21 Nov
2-Bdr Apt In Town, By the Water
Indoor pool
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)
"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 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Outdoor dining
Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops

Williamstown
10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is AED 477
AED 1,016 total
includes taxes & fees
20 Nov - 21 Nov
Downtown | Waterfront | Walk to Shops
Exterior
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)
"Nice Place"
United States
Tom C.
The price is AED 404
AED 886 total
includes taxes & fees
20 Nov - 21 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Hancock
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is AED 386
AED 866 total
includes taxes & fees
20 Nov - 21 Nov
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel

Stephentown
10.0 out of 10, Exceptional, (3)
"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 354
AED 788 total
includes taxes & fees
23 Nov - 24 Nov
Berkshires Apartment at the Stephentown Hotel
Fridge, microwave, oven, stovetop
New Studio In Town, By the Water

New Studio In Town, By the Water

Williamstown
10.0 out of 10, Exceptional, (10)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is AED 441
AED 945 total
includes taxes & fees
20 Nov - 21 Nov
New Studio In Town, By the Water
3 bedrooms, iron/ironing board, WiFi, bed sheets
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)
"as advertised."
United States
Joshua G.
The price is AED 1,273
AED 2,306 total
includes taxes & fees
20 Nov - 21 Nov
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Exterior
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, (30)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is AED 584
AED 1,198 total
includes taxes & fees
24 Nov - 25 Nov
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior
Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath

Shelburne Falls
Rose room Victorian home queen bed private bath
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 505
AED 946 total
includes taxes & fees
20 Nov - 21 Nov
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Outdoor dining
The Allen House historic North Adams Home in the Berkshire Mountains

The Allen House historic North Adams Home in the Berkshire Mountains

2.0 star property
North Adams
The price is AED 672
AED 1,182 total
includes taxes & fees
4 Dec - 5 Dec
The Allen House historic North Adams Home in the Berkshire Mountains
Pool
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, (3)
"Great room decorations, travel with two kids they have a great time playing video games"
United States
Andres
The price is AED 386
AED 866 total
includes taxes & fees
20 Nov - 21 Nov
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Exterior
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)
"Great location. Very nice vacation. Would def go again. "
United States
Elizabeth M.
The price is AED 404
AED 886 total
includes taxes & fees
20 Nov - 21 Nov
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"My room was amazing nice view of the mountains the staff were very friendly they have a beautiful indoor pool amazing hot tub and cute movie theater along with a game room and other activities "
Teresa 2-night trip
Posted 2 days ago
Vacation Village in the Berkshires

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: 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. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor: Located in Hancock, 6.5 mi/10.5 km away. Includes sofa beds. A fitness center and an indoor pool are 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. 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 Cheshire. Includes a private pool, free WiFi, and private patios. 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.