Find hotels in Cheshire, MA from ₩93,639

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Our top choices for Cheshire hotels

Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is ₩313,709
₩331,591 total
includes taxes & fees
Jan 12 - Jan 13
Harbour House Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,000 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is ₩137,579
₩153,677 total
includes taxes & fees
Jan 25 - Jan 26
Best Western Plus Berkshire Hills Inn & Suites
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,004 reviews)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is ₩142,993
₩159,729 total
includes taxes & fees
Jan 23 - Jan 24
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,004 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ₩142,628
₩159,315 total
includes taxes & fees
Feb 1 - Feb 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Front of property
Blooming Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (128 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is ₩131,320
₩218,180 total
includes taxes & fees
Jan 12 - Jan 13
Blooming Inn
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is ₩119,618
₩133,613 total
includes taxes & fees
Feb 1 - Feb 2
Quality Inn Lee - Lenox South
Gazebo
Cozy Corner Motel

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (889 reviews)
"Excellent service and a beautifully decorated property."
United States
Ivana
The price is ₩101,116
₩119,632 total
includes taxes & fees
Feb 1 - Feb 2
Cozy Corner Motel
Lobby lounge
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is ₩202,816
₩226,545 total
includes taxes & fees
Jan 19 - Jan 20
Element Lenox Berkshires
In-room safe, desk, laptop workspace, iron/ironing board
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is ₩115,270
₩128,752 total
includes taxes & fees
Jan 12 - Jan 13
Howard Johnson by Wyndham Lenox
Property grounds
Willows Motel Williamstown

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (999 reviews)
"Convenient location & a clean room"
United States
Stephanie
The price is ₩111,622
₩124,681 total
includes taxes & fees
Jan 12 - Jan 13
Willows Motel Williamstown
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Everything was great! "
Canada
Daphne
The price is ₩147,589
₩164,858 total
includes taxes & fees
Jan 19 - Jan 20
The Yankee, Trademark Collection by Wyndham
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (440 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is ₩159,043
₩174,471 total
includes taxes & fees
Jan 13 - Jan 14
Shaker Mill Inn
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (818 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is ₩164,150
₩211,881 total
includes taxes & fees
Jan 13 - Jan 14
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,002 reviews)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is ₩182,447
₩203,793 total
includes taxes & fees
Feb 2 - Feb 3
Hotel Downstreet, an Ascend Collection Hotel
Lobby lounge
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Very comfortable beds! "
United States
Gerald
The price is ₩162,253
₩181,238 total
includes taxes & fees
Jan 25 - Jan 26
Hampton Inn & Suites Berkshires-Lenox
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (661 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is ₩186,591
₩208,419 total
includes taxes & fees
Jan 23 - Jan 24
Hilton Garden Inn Lenox Pittsfield
Reception
The Villager Motel

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (768 reviews)
"It's very good for stay over"
United States
Frances
The price is ₩109,433
₩122,244 total
includes taxes & fees
Jan 12 - Jan 13
The Villager Motel
Exterior
Blue Vista Motor Lodge

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (197 reviews)
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
The price is ₩260,582
₩275,436 total
includes taxes & fees
Jan 12 - Jan 13
Blue Vista Motor Lodge
Mountain view
Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (899 reviews)
"Great affordable place to stay while in the northern Berkshires."
United States
PAUL
The price is ₩131,305
₩146,669 total
includes taxes & fees
Jan 12 - Jan 13
Howard Johnson by Wyndham Williamstown
Property grounds
Maple Terrace Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (595 reviews)
"Cute place"
United States
Lisa
The price is ₩144,452
₩161,348 total
includes taxes & fees
Jan 14 - Jan 15
Maple Terrace Motel
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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Stay near popular Cheshire attractions

St Mary's of the Assumption Church

St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views, or seek out its ski slopes.
See properties

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting.

See all hotels in Cheshire
An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Top Cheshire Hotel Reviews

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent
"Extraordinary"
Lee 2-night trip
Posted 4 days ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

More cheap stays in Cheshire

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is ₩115,270 per night from Jan 12 to Jan 13
₩115,270
₩128,752 total
Jan 12 - Jan 13
includes taxes & fees
7.4/10 Good! (827 reviews)

Frequently asked questions

What's the best place to stay in Cheshire?
Located 6.5 mi (10.5 km) from the heart of Cheshire, Vacation Village in the Berkshires is a top choice for your stay based on our traveler data. Other good options for your stay in the area are Hotel Downstreet, an Ascend Collection Hotel and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or vacation rentals in Cheshire.
If I need to cancel my hotel reservation in Cheshire, will I receive a refund?
Yes! Most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
Where can I learn more about changing or cancelling my trip to Cheshire?
To find more details about updating your trip to Cheshire or cancelling it, click here.
What is the favorite LGBTQ-friendly accommodation in Cheshire?
Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi. See all available hotels listed as LGBTQ-friendly in Cheshire.
What are some hotels with pools in Cheshire?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel and Holiday Inn & Suites Pittsfield-Berkshires by IHG are two additional hotels with an onsite pool. View all hotels with pools in Cheshire.
What is the best hotel near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What is staying in Cheshire like?
Visitors can enjoy all that Cheshire has to offer including the ski areas, restaurants, and lake views. Tourists can also enjoy so much more including its shopping. In Cheshire, there are 6 hotels and other accommodations to choose from. Find out more about Cheshire.
What are the top places to visit in Cheshire?
A favorite place to visit is Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock in the area. Check out what more to see and do in Expedia's Cheshire guide.
What's the seasonal weather like 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.

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