Find hotels in Cheshire, MA from ฿2,568

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9 Jan - 10 Jan
Tomorrow
10 Jan - 11 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

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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)
"Nice place for a weekend away."
United States
Gregory
The price is ฿6,735
฿7,119 total
includes taxes & fees
21 Jan - 22 Jan
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, (1000)
"Very friendly and good Breakfast."
United States
Jesse
The price is ฿2,393
฿2,672 total
includes taxes & fees
25 Jan - 26 Jan
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, (1002)
"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 ฿3,081
฿3,442 total
includes taxes & fees
23 Jan - 24 Jan
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, (1003)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ฿3,073
฿3,433 total
includes taxes & fees
29 Jan - 30 Jan
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, (127)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is ฿2,819
฿4,684 total
includes taxes & fees
11 Jan - 12 Jan
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, (1000)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is ฿2,582
฿2,884 total
includes taxes & fees
1 Feb - 2 Feb
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)
"Excellent service and a beautifully decorated property."
United States
Ivana
The price is ฿2,171
฿2,568 total
includes taxes & fees
8 Feb - 9 Feb
Cozy Corner Motel
Lobby lounge
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (15)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is ฿4,354
฿4,864 total
includes taxes & fees
25 Jan - 26 Jan
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)
"Staff was very friendly and helpful."
United States
Pamela
The price is ฿2,475
฿2,764 total
includes taxes & fees
13 Jan - 14 Jan
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)
"Convenient location & a clean room"
United States
Stephanie
The price is ฿2,396
฿2,677 total
includes taxes & fees
16 Jan - 17 Jan
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, (1000)
"Everything was great! "
Canada
Daphne
The price is ฿3,180
฿3,552 total
includes taxes & fees
19 Jan - 20 Jan
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)
"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 ฿3,427
฿3,759 total
includes taxes & fees
13 Jan - 14 Jan
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)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is ฿2,932
฿3,888 total
includes taxes & fees
13 Jan - 14 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
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, (1002)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is ฿3,931
฿4,391 total
includes taxes & fees
2 Feb - 3 Feb
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, (1000)
"Very comfortable beds! "
United States
Gerald
The price is ฿3,483
฿3,891 total
includes taxes & fees
25 Jan - 26 Jan
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)
" Nice staff - beautiful hotel!"
United States
MARY
The price is ฿4,021
฿4,491 total
includes taxes & fees
23 Jan - 24 Jan
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)
"It's very good for stay over"
United States
Frances
The price is ฿2,349
฿2,624 total
includes taxes & fees
19 Jan - 20 Jan
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)
"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 ฿5,595
฿5,913 total
includes taxes & fees
20 Jan - 21 Jan
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)
"Great affordable place to stay while in the northern Berkshires."
United States
PAUL
The price is ฿2,819
฿3,149 total
includes taxes & fees
17 Jan - 18 Jan
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)
"Cute place"
United States
Lisa
The price is ฿3,101
฿3,464 total
includes taxes & fees
21 Jan - 22 Jan
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 local cuisine.

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

Top Cheshire Hotel Reviews

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

10/10 Excellent
"Very good "
Fernando 5-night trip
Posted 4 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap stays in Cheshire

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA
The price is ฿2,393 per night from 25 Jan to 26 Jan
฿2,393
฿2,672 total
25 Jan - 26 Jan
includes taxes & fees
8.4/10 Very Good! (1,002 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 traveller data. Two other choices for your trip to the area are Hotel Downstreet, an Ascend Collection Hotel and The Williams Inn. 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 room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
What's the best LGBTQ-friendly place to stay 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 that feature an on-site pool. View all hotels with pools in Cheshire.
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 5 hotels and other accommodation options to choose from. Find out more about Cheshire.
What is there to see in Cheshire?
A favourite place to visit is Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Adams Theater in the area. Take a look at what more there is to see and do in Expedia's Cheshire guide.
What's the seasonal weather in Cheshire?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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