A lake surrounded by autumn-colored trees and hills.

Find hotels in Cheshire, MA from ฿2,323

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Check prices for these dates

This weekend
17 Jul - 19 Jul
Next weekend
24 Jul - 26 Jul

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Our top choices for Cheshire hotels

Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (55 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is ฿8,495
฿8,979 total
includes taxes & fees
21 Jul - 22 Jul
Harbour House Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,014 reviews)
"Great place"
United States
Michelle
The price is ฿4,422
฿4,939 total
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Lee - Lenox South
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,016 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
The price is ฿6,329
฿7,069 total
includes taxes & fees
19 Jul - 20 Jul
The Yankee Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout curtains

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, (1,007 reviews)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
The price is ฿3,954
฿4,417 total
includes taxes & fees
2 Aug - 3 Aug
Best Western Plus Berkshire Hills Inn & Suites
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (491 reviews)
"We needed a bed for a quick crash session on the way through. The gentleman at the front desk was pleasant and so helpful and kind."
United States
Kyle
The price is ฿2,260
฿2,531 total
includes taxes & fees
19 Jul - 20 Jul
Berkshire Travel Lodge
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (929 reviews)
"Very nice and cute place to stay. Staff was very friendly and helpful. Room was nice and clean. Very quiet with beautiful outside property. The only problem was no coffee or breakfast until 8am."
United States
Tracy
The price is ฿3,044
฿3,575 total
includes taxes & fees
21 Jul - 22 Jul
Cozy Corner Motel
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (852 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
The price is ฿2,079
฿2,323 total
includes taxes & fees
29 Jul - 30 Jul
FairBridge Inn Express
Indoor pool, open 6:00 AM to 10 PM, pool loungers

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,001 reviews)
"Quick check in and comfortable bed in a pretty New England town."
United States
William
The price is ฿5,759
฿6,433 total
includes taxes & fees
20 Jul - 21 Jul
Hotel Downstreet, an Ascend Collection Hotel
Mountain view

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (921 reviews)
"It's an older hotel however very clean & neat. The breakfast was very nice."
United States
Josephine
The price is ฿3,348
฿3,740 total
includes taxes & fees
16 Jul - 17 Jul
Howard Johnson by Wyndham Williamstown
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (620 reviews)
"Adorable little place! Staff was incredible and the rooms were cute but the only downside was the rooms had an older home smell!"
United States
Stephanie
The price is ฿4,654
฿5,199 total
includes taxes & fees
19 Jul - 20 Jul
Maple Terrace Motel
Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, free WiFi, bed sheets

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (257 reviews)
"Liked that fact that they let your bring your pet."
United States
Andrew
The price is ฿2,831
฿3,162 total
includes taxes & fees
20 Jul - 21 Jul
Rodeway Inn
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (801 reviews)
"The price in this area is expensive and this motel provides a reasonable alternative!"
United States
qing
The price is ฿3,315
฿3,703 total
includes taxes & fees
16 Jul - 17 Jul
The Villager Motel
Children’s activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Very comfortable. Will stay there again"
United States
Peter
The price is ฿2,260
฿2,479 total
includes taxes & fees
19 Jul - 20 Jul
Pleasant Valley Motel West Stockbridge
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (880 reviews)
"Clean, quiet, friendly, no frills but everything needed. Mattresses were very good."
United States
James
The price is ฿3,013
฿3,366 total
includes taxes & fees
19 Jul - 20 Jul
Berkshire Inn
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,000 reviews)
"Great value and excellent location"
United States
Truett
The price is ฿3,149
฿3,518 total
includes taxes & fees
20 Jul - 21 Jul
Willows Motel Williamstown
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,446 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is ฿4,408
฿5,291 total
includes taxes & fees
9 Aug - 10 Aug
Vacation Village in the Berkshires
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (112 reviews)
"Nice stay for a day with family.."
United States
Raghvendra
The price is ฿3,767
฿4,182 total
includes taxes & fees
16 Jul - 17 Jul
Gregory House Country Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (464 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ฿6,463
฿7,089 total
includes taxes & fees
20 Jul - 21 Jul
Shaker Mill Inn
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (884 reviews)
"Great place"
United States
Luciane
The price is ฿3,315
฿3,703 total
includes taxes & fees
16 Jul - 17 Jul
Howard Johnson by Wyndham Lenox
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (134 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
The price is ฿5,559
฿6,209 total
includes taxes & fees
19 Jul - 20 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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

10.0/10 (1 review)
This historic Catholic parish has served Cheshire's community since 1879, offering a serene space for reflection. Visit during religious holidays to experience special services in its traditional architectural setting.
See properties

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking and lake views.

See all hotels in Cheshire
A lake surrounded by autumn-colored trees and hills.

Top Cheshire Hotel Reviews

The Whitlock

The Whitlock

10/10 Excellent
"Great location and nice hotel."
William 3-night trip
Posted 1 hour ago
The Whitlock

More cheap stays in Cheshire

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is ฿2,079 per night from 29 Jul to 30 Jul
฿2,079
฿2,323 total
29 Jul - 30 Jul
includes taxes & fees
5.4/10 (852 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 The Yankee Inn and Berkshire Mountain Lodge. 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. The Yankee Inn and Berkshire Mountain Lodge 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 6 hotels and other accommodation options to choose from. Find out more about Cheshire.
What is there to see in Cheshire?
The picturesque setting of Mount Greylock State Reservation and Cheshire Reservoir exemplify the area's natural beauty. You'll also find Mount Greylock State Reservation Visitor Center and Susan B. Anthony Birthplace Museum 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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