A lake surrounded by autumn-colored trees and hills.

Cheshire hotels from HK$566

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Check prices for these dates

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13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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Our top choices for Cheshire hotels

A breakfast setting with a plate of food, a glass of orange juice, and a cup of tea.

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.8 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is HK$1,990
HK$2,104 total
includes taxes & fees
30 Nov - 1 Dec
Harbour House Inn
A reception area with a large landscape painting, a dark reception desk, and a potted plant.

2. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,000 reviews)
"Had a great time at this wonderful hotel."
United States
marwan
The price is HK$935
HK$1,045 total
includes taxes & fees
26 Nov - 27 Nov
Hotel Downstreet, an Ascend Collection Hotel
A gym with treadmills, an elliptical, and weight machines.

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,844 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is HK$630
HK$790 total
includes taxes & fees
15 Nov - 16 Nov
Vacation Village in the Berkshires
A patio area with outdoor furniture, a fire pit, and potted plants.

4. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.0 out of 10, Wonderful, (124 reviews)
"Loved the vibe!"
United States
Elizabeth
The price is HK$830
HK$910 total
includes taxes & fees
10 Dec - 11 Dec
The Springs Motel
A fire feature with a metal frame and a brick wall in the background.

5. Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
3.0 star property
Williamstown
8.8 out of 10, Excellent, (441 reviews)
"Nicer than your average ~$150 hotels. Clean room, but the details were better than the local Holiday Inn, etc. Would stay again."
United States
Josh
The price is HK$1,201
HK$1,342 total
includes taxes & fees
29 Nov - 30 Nov
Fairfield Inn & Suites by Marriott Williamstown
A bedroom with a bed, a sofa, a fireplace, and a chandelier.

6. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (46 reviews)
"Nice historic, Inn like feeling. Comfy rooms, easy breakfast until 1pm!! Staff responsive via SMS almost 24/7"
United States
Ruby
The price is HK$1,083
HK$1,210 total
includes taxes & fees
29 Nov - 30 Nov
The Revival House
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

7. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (531 reviews)
"always enjoy staying here!"
United States
Evonne
The price is HK$1,264
HK$1,587 total
includes taxes & fees
15 Nov - 16 Nov
The Porches Inn at Mass MoCA
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

8. The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (714 reviews)
"Fantastic hotel! Would definitely stay again."
United States
Pete
The price is HK$1,594
HK$1,780 total
includes taxes & fees
15 Nov - 16 Nov
The Williams Inn
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

9. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (984 reviews)
"Staff very pleasant and accommodating."
United States
Rosemarie
The price is HK$911
HK$1,017 total
includes taxes & fees
29 Nov - 30 Nov
Hotel On North
A white two-story building with a porch, labeled as a motel.

10. Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (1,000 reviews)
"Outstanding bed and breakfast in Williamstown, walking distance to the college, and also close to Mass MOCA. Will be staying there again. The fresh fruit was absolutely outstanding."
United States
Anuj
The price is HK$663
HK$741 total
includes taxes & fees
24 Nov - 25 Nov
Willows Motel Williamstown
A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.

11. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.4 out of 10, Very good, (1,004 reviews)
"Nice resort and friendly staff."
United States
Olga
The price is HK$1,052
HK$1,175 total
includes taxes & fees
14 Nov - 15 Nov
Jiminy Peak Mountain Resort
Two Adirondack chairs facing a river with a forested hill in the background.

12. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"What a beautiful stay. Room was so clean ! Great food selection for breakfast."
United States
Stephanie
The price is HK$988
HK$1,104 total
includes taxes & fees
12 Dec - 13 Dec
The Yankee Inn
An indoor swimming pool with clear water, tiled floors, and a blue wall.

13. 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, (258 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is HK$808
HK$903 total
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A covered balcony with a table and two white wire chairs, a bowl of fruit, and a glass of juice.

14. The Trail in Adams - Berkshiresā€™ Art Hotel

The Trail in Adams - Berkshiresā€™ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (159 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is HK$1,363
HK$1,522 total
includes taxes & fees
30 Nov - 1 Dec
The Trail in Adams - Berkshiresā€™ Art Hotel
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

15. Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (285 reviews)
"The motel was clean and somewhat updated. Check in and check out was easy. Across the street was a yummy pizzeria."
United States
Joann
The price is HK$507
HK$566 total
includes taxes & fees
13 Dec - 14 Dec
Rodeway Inn
A building with a covered parking area and a grassy front yard.

16. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (964 reviews)
"Needed a home away from home when a renovation turned into a nightmare. The family who runs this place are lovely and kind, the hotel is clean if a bit older. Solid choice in the area. Will let friends and family know if they are coming, simple clean hotel."
United States
Kate
The price is HK$784
HK$876 total
includes taxes & fees
29 Nov - 30 Nov
Howard Johnson by Wyndham Williamstown
A garden with a swing set, a blue chair, and a flower bed.

17. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (648 reviews)
"Perfect charming little hotel The couple at the front was very nice and helpful"
United States
yeraldine
The price is HK$777
HK$867 total
includes taxes & fees
24 Nov - 25 Nov
Maple Terrace Motel
A reception area with a wooden reception desk, a seating area with sofas, a colorful stained glass window, a mounted television, and various potted plants.

18. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,002 reviews)
"Room was spacious and clean"
United States
James
The price is HK$733
HK$819 total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites
A living room with two armchairs, a coffee table, a potted plant, and a kitchen area with a refrigerator.

19. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (936 reviews)
"Friendly staff"
United States
William
The price is HK$558
HK$623 total
includes taxes & fees
15 Nov - 16 Nov
FairBridge Inn Express
A spacious hotel lobby with multiple seating areas, large windows, and a television.

20. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"Breakfast was great"
United States
Thomas
The price is HK$860
HK$961 total
includes taxes & fees
22 Nov - 23 Nov
Hampton Inn & Suites Berkshires-Lenox
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 natural setting.

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

Top Cheshire Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Breakfast was h asic everything else was perfect"
paul 2-night trip
Posted 15 hours ago
The Yankee Inn

More cheap stays in Cheshire

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is HK$558 per night from 15 Nov to 16 Nov
HK$558
HK$623 total
15 Nov - 16 Nov
includes taxes & fees

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 17Ā°C, while the coldest months are January and February, with an average of -4Ā°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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