A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Cheshire apartments

Exterior

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (33 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Property grounds

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
The price is CA $201
CA $370 total
includes taxes & fees
Jul 13 - Jul 14
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Exterior

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is CA $165
CA $298 total
includes taxes & fees
Jul 13 - Jul 14
Rose room Victorian home queen bed private bath
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (8 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is CA $178
CA $398 total
includes taxes & fees
Jul 9 - Jul 10
Downtown | Waterfront | Walk to Shops
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (13 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is CA $170
CA $398 total
includes taxes & fees
Jul 9 - Jul 10
2-Bdr Apt In Town, By the Water
Dining

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40 reviews)
"Clean, friendly, but isolated. On premises coffee shop was a bonus."
United States
Karl K.
The price is CA $192
CA $292 total
includes taxes & fees
Jul 16 - Jul 17
Charming Apt in 18th c Berkshire Farmhouse
Property grounds

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is CA $197
CA $393 total
includes taxes & fees
Jul 9 - Jul 10
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
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 CA $197
CA $393 total
includes taxes & fees
Jul 9 - Jul 10
Gorgeous Mountain View Suite Ski On/Off At Jiminy - 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, (14 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is CA $192
CA $409 total
includes taxes & fees
Jul 15 - Jul 16
New Studio In Town, By the Water
Gift shop

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, (12 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is CA $206
CA $404 total
includes taxes & fees
Jul 9 - Jul 10
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Living area

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (14 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is CA $206
CA $398 total
includes taxes & fees
Jul 29 - Jul 30
Penthouse Apartment on Park Street
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 skiing and proximity to mountain. Great for families"
United States
John F.
The price is CA $197
CA $393 total
includes taxes & fees
Jul 9 - Jul 10
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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
9.6 out of 10, Exceptional, (17 reviews)
"Host very responsive. I gave feedback that could make stay better like more hangars and some coat hooks. Massage chair in unit was a hit with the whole family.Unit is literally the last unit in last builing of Coubtry Inn away from ski school and Express lift. Still walkable, just not in ski boots.Parking in front of unit super easy.No elevator nearby. Upstairs with luggage. "
United States
Joe C.
The price is CA $197
CA $393 total
includes taxes & fees
Jul 9 - Jul 10
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
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 CA $154
CA $284 total
includes taxes & fees
Jul 13 - Jul 14
2 Twin beds on 1st floor with En-suite bathroom.
Exterior

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Everything was wonderful…"
United States
Alyne K.
The price is CA $197
CA $393 total
includes taxes & fees
Jul 9 - Jul 10
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
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 CA $249
CA $496 total
includes taxes & fees
Jul 9 - Jul 10
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
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, (5 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 CA $197
CA $393 total
includes taxes & fees
Jul 9 - Jul 10
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Exterior

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is CA $230
CA $433 total
includes taxes & fees
Jul 27 - Jul 28
Rose wisteria 4 guests 2 bedrooms-full+queen beds
TV, fireplace, DVD player

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
The price is CA $290
CA $548 total
includes taxes & fees
Jul 9 - Jul 10
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
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
9.8 out of 10, Exceptional, (6 reviews)
"Gorgeous views even in March, ample heating/cooling, wonderful host experience, would just recommend bringing paper plates/utensils as we found ourselves running the dishwasher often. "
United States
avery o.
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Really liked how updated the room was and very clean, it had a refrigerator which was perfect for someone who travels for work , wish it had a microwave in my room- that would be perfect I would stay again for sure Breakfast was really good and I like that it starts early enough so I can eat before my work shift starts"
stacy 1-night trip
Posted 11 hours ago
Hampton Inn & Suites Berkshires-Lenox

Find out more about Cheshire

Cheshire Apartments information

Number of reviews
214
Accommodation
99 Apartments
Lowest Price
CA $284
Highest Price
CA $548

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: Revitalized Firehouse Retreat in Downtown Shelburne Falls. Walk to Everything!: Located in Shelburne Falls, 21.6 mi/34.7 km from the heart of Cheshire. Includes Smart TVs. Access to onsite laundry facilities is available on site. 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. New Studio In Town, By the Water: Located in Williamstown, 10.3 mi/16.5 km away. Includes free WiFi, private balconies, and sofa beds. 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 16.3 mi/26.2 km away in Pownal. A private pool, free WiFi, and private patios are included. 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?
Mount Greylock State Reservation and Cheshire Reservoir are a couple of lovely local spots to get outside and enjoy nature. 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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