A lake surrounded by autumn-colored trees and hills.

Cheshire hotels from HK$544

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Check prices for these dates

Tonight
26 Sept - 27 Sept
Tomorrow
27 Sept - 28 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

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Our top choices for Cheshire hotels

1. Harbour House Inn

Harbour House Inn
Cheshire
United States
Gregory
HK$1,990
HK$2,103 total
includes taxes & fees
28 Sept - 29 Sept
Harbour House Inn

2. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
HK$873
HK$958 total
includes taxes & fees
28 Sept - 29 Sept
The Springs Motel

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Jacob
HK$746
HK$920 total
includes taxes & fees
27 Sept - 28 Sept
Vacation Village in the Berkshires

4. The Revival House

The Revival House
Adams
United States
Katrina
HK$1,299
HK$1,451 total
includes taxes & fees
27 Sept - 28 Sept
The Revival House

5. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
United States
Linda
HK$812
HK$907 total
includes taxes & fees
28 Sept - 29 Sept
Willows Motel Williamstown

6. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
Alexandra
HK$1,060
HK$1,184 total
includes taxes & fees
14 Oct - 15 Oct
Hotel Downstreet, an Ascend Collection Hotel

7. Maple Terrace Motel

Maple Terrace Motel
Williamstown
United States
Deborah
HK$1,012
HK$1,130 total
includes taxes & fees
28 Sept - 29 Sept
Maple Terrace Motel

8. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
United States
Horace
HK$487
HK$544 total
includes taxes & fees
28 Sept - 29 Sept
FairBridge Inn Express

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Susan
HK$957
HK$1,069 total
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10. Cozy Corner Motel

Cozy Corner Motel
Williamstown
United States
Jonathan
HK$692
HK$813 total
includes taxes & fees
28 Sept - 29 Sept
Cozy Corner Motel

11. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
HK$839
HK$938 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn & Suites Pittsfield-Berkshires by IHG

12. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
United States
COLLEEN
HK$620
HK$692 total
includes taxes & fees
27 Sept - 28 Sept
Howard Johnson by Wyndham Lenox

13. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
Joe
HK$830
HK$927 total
includes taxes & fees
19 Oct - 20 Oct
Best Western Plus Berkshire Hills Inn & Suites

14. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
Adams
United States
Susan
HK$1,421
HK$1,588 total
includes taxes & fees
28 Sept - 29 Sept
The Trail in Adams - Berkshires’ Art Hotel

15. Hotel On North

Hotel On North
Pittsfield
United States
Drew
HK$1,053
HK$1,176 total
includes taxes & fees
5 Oct - 6 Oct
Hotel On North

16. The Yankee Inn

The Yankee Inn
Lenox
United States
William
HK$847
HK$946 total
includes taxes & fees
27 Oct - 28 Oct
The Yankee Inn

17. The Williams Inn

The Williams Inn
Williamstown
United States
William
HK$1,524
HK$1,702 total
includes taxes & fees
27 Sept - 28 Sept
The Williams Inn

18. Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
Williamstown
United States
C. David
HK$1,408
HK$1,573 total
includes taxes & fees
1 Oct - 2 Oct
Fairfield Inn & Suites by Marriott Williamstown

19. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Kristina
HK$674
HK$753 total
includes taxes & fees
28 Sept - 29 Sept
Berkshire Inn

20. Williamstown Motel

Williamstown Motel
Williamstown
United States
Ahmet
HK$863
HK$964 total
includes taxes & fees
27 Sept - 28 Sept
Williamstown Motel
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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 natural setting.

See all hotels in Cheshire
A lake surrounded by autumn-colored trees with a clear sky.

Top Cheshire Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"It’s an older facility , as expected, but with great character and very clean . Special praise goes to the staff , in particular , Michele at the front desk . Super nice and very helpful in answering our questions about the local activities . Will keep in mind for another visit ."
Saed 1-night trip
Posted 8 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold

Berkshires Untold

10/10 Excellent
"Love the property, room seemed a little tired since I was there last, about 3 years ago. Wish we could stay just one night instead of minimum two, as we often come just for a Tanglewood concert and stay only one night in town."
Sue 2-night trip
Posted 10 hours ago
Berkshires Untold
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"I stayed in a townhouse, an upgrade from the room I booked. It was quiet and private, which I enjoyed, and more room than I needed. If my family's schedule had been different, I could have invited them over for a cookout (they live nearby). The townhouse was rather dated and I am afraid a bit dreary, with a lot of browns and beiges. But well-outfitted and convenient."
Diane 5-night trip
Posted 10 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Very clean and comfortable. Some of the mechanicals are older but the rooms are quite fresh. Excellent location. Pretty good breakfast. Excellent value."
Louis 1-night trip
Posted 12 hours ago
Quality Inn Lee - Lenox South
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"A most amazing place to stay! Has everything a hotel should have - we had a very large room! Great porch! We have stayed there several times."
Roger 1-night trip
Posted 15 hours ago
The Red Lion Inn
The Whitlock

The Whitlock

10/10 Excellent
"The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property."
Michael 1-night trip
Posted 16 hours ago
The Whitlock
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"Toilet was faulty but they gave us another room. Not much variety on the breakfast"
Ron 3-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"One of the most important aspects of a good hotel is the smell of it when I first walk in the door. This lodge smelled clean and was clean. The second important thing is the customer service. This place was just okay. Polite but not very friendly. The third important aspect is the plumbing and that was just okay too. Workable enough so we didn’t have to ask for another room but the little soaps were tiny and the toilet was in okay condition. A little hard to flush sometimes. They act like it’s someplace special but it really isn’t. It was a good stay but nothing special. Location was convenient to everything - restaurants and stores."
Karen 2-night trip
Posted 3 days ago
Berkshire Mountain Lodge
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."
Karl 1-night trip
Posted 3 days ago
Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in Cheshire

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
HK$487
HK$544 total
28 Sept - 29 Sept
includes taxes & fees
FairBridge Inn Express
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
HK$620
HK$692 total
27 Sept - 28 Sept
includes taxes & fees
7.6/10 Good! (917 reviews)
Howard Johnson by Wyndham Lenox
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
HK$847
HK$946 total
27 Oct - 28 Oct
includes taxes & fees
The Yankee Inn
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA
HK$860
HK$961 total
19 Oct - 20 Oct
includes taxes & fees
8.4/10 Very good! (1,006 reviews)
Quality Inn Lee - Lenox South
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
HK$957
HK$1,069 total
19 Oct - 20 Oct
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Whitlock

The Whitlock

16 Church St Lenox MA
HK$1,087
HK$1,214 total
28 Sept - 29 Sept
includes taxes & fees
8.4/10 Very good! (387 reviews)
The Whitlock

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 Berkshire Mountain Lodge and The Yankee Inn. See all available top hotels, or vacation rentals in Cheshire.
What are some of the best holiday rentals that Cheshire has to offer?
Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Cheshire is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. See all 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: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge and The Yankee Inn 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 Mount Greylock 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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