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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Apartments in Cheshire

Spacious & Cozy Ground Floor 2/3 Bed private suite
Property grounds

Spacious & Cozy Ground Floor 2/3 Bed private suite

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great property and location for a visit to Shelburne Falls. "
The price is AED 586
AED 1,319 total
includes taxes & fees
6 Oct - 7 Oct
Spacious & Cozy Ground Floor 2/3 Bed private suite
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is AED 1,414
AED 2,481 total
includes taxes & fees
2 Nov - 3 Nov
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Berkshires Apartment at the Stephentown Hotel
Fridge, microwave, oven, stovetop

Berkshires Apartment at the Stephentown Hotel

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."
The price is AED 413
AED 823 total
includes taxes & fees
6 Oct - 7 Oct
Berkshires Apartment at the Stephentown Hotel
Downtown | Waterfront | Walk to Shops
Outdoor dining

Downtown | Waterfront | Walk to Shops

10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
The price is AED 496
AED 1,033 total
includes taxes & fees
26 Oct - 27 Oct
Downtown | Waterfront | Walk to Shops
Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain
TV, DVD player, books

Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain

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!!"
The price is AED 397
AED 878 total
includes taxes & fees
6 Oct - 7 Oct
Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain
Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.6 out of 10, Exceptional, (11)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
The price is AED 551
AED 1,050 total
includes taxes & fees
26 Oct - 27 Oct
Park Street Penthouse Apartment
New Studio In Town, By the Water
Fridge, microwave, oven, stovetop

New Studio In Town, By the Water

10.0 out of 10, Exceptional, (8)
"Great location, we really enjoyed our stay! "
The price is AED 441
AED 941 total
includes taxes & fees
8 Oct - 9 Oct
New Studio In Town, By the Water
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. "
The price is AED 382
AED 857 total
includes taxes & fees
6 Oct - 7 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Exterior

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

10.0 out of 10, Exceptional, (4)
"It was great experience and we loved the ammenities."
The price is AED 397
AED 878 total
includes taxes & fees
6 Oct - 7 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Exterior

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

9.6 out of 10, Exceptional, (30)
"Perfect 1 bedroom, ski in ski off , updated unit with great amenities! Owner super responsive and accommodating. Will definitely be back "
The price is AED 382
AED 857 total
includes taxes & fees
6 Oct - 7 Oct
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Indoor pool

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

9.8 out of 10, Exceptional, (18)
"We had a great time with our 2 kids during our stay at the Disney Magic Suite. The kids loved all of the Disney decor and surprise touches (and their stuffed animals thank you!). Location was amazing, walk to the lifts, and the ski school was one of the best we've been to. Thanks for a great stay, we'll be back!"
The price is AED 397
AED 878 total
includes taxes & fees
6 Oct - 7 Oct
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
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, (30)
"We really enjoyed our stay it was a very nice place for a family."
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Living area

Rose wisteria 4 guests 2 bedrooms-full+queen beds

The price is AED 505
AED 954 total
includes taxes & fees
22 Oct - 23 Oct
Rose wisteria 4 guests 2 bedrooms-full+queen beds
2-Bdr Apt In Town, By the Water
Outdoor dining

2-Bdr Apt In Town, By the Water

9.6 out of 10, Exceptional, (8)
"Lovely property, in good shape. Close to many Williamstown attractions."
The price is AED 441
AED 983 total
includes taxes & fees
26 Oct - 27 Oct
2-Bdr Apt In Town, By the Water
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)
"Stayed one night at one of my favorite ski spots. Will be back again!"
The price is AED 397
AED 878 total
includes taxes & fees
6 Oct - 7 Oct
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
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
"Very nice!"
PATRICIA 2-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

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. 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. Charming Apt in 18th c Berkshire Farmhouse: Located in Lanesborough, 3.9 mi/6.3 km away. 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.
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.