Hotels in Cheshire

Q: What accommodations do travelers like in Cheshire?

Guests like Vacation Village in the Berkshires , Hotel Downstreet, an Ascend Collection Hotel and FairBridge Inn Express .

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Where to stay in Cheshire?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Cheshire on Hotels.com. These Cheshire hotels consistently deliver on quality, location and traveler experience. Last updated on October 27, 2026.

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

1. Harbour House Inn

Cheshire

CNY1,788 total

includes taxes & fees

Oct 28 - Oct 29

2. Hotel Downstreet, an Ascend Collection Hotel

North Adams

CNY888 total

includes taxes & fees

Nov 16 - Nov 17

Two Adirondack chairs facing a river with a forested hill in the background.

3. The Yankee Inn

Lenox

CNY790 total

includes taxes & fees

Nov 1 - Nov 2

A patio area with outdoor furniture, a fire pit, and potted plants.

4. The Springs Motel

New Ashford

CNY774 total

includes taxes & fees

Oct 28 - Oct 29

A living room with a fireplace, two sofas, and four black side tables.

5. The Revival House

Adams

CNY1,118 total

includes taxes & fees

Nov 1 - Nov 2

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

6. The Porches Inn at Mass MoCA

North Adams

CNY1,317 total

includes taxes & fees

Nov 25 - Nov 26

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

7. Vacation Village in the Berkshires

Williamstown

CNY672 total

includes taxes & fees

Nov 1 - Nov 2

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

Williamstown

CNY1,513 total

includes taxes & fees

Nov 8 - Nov 9

A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

9. The Trail in Adams - Berkshires’ Art Hotel

Adams

CNY1,294 total

includes taxes & fees

Nov 1 - Nov 2

A building entrance with a large planter with purple flowers and a small tree.

10. Hotel On North

Pittsfield

CNY932 total

includes taxes & fees

Nov 9 - Nov 10

A fire feature with a metal frame and a brick wall in the background.

11. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

CNY1,075 total

includes taxes & fees

Nov 15 - Nov 16

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

12. Willows Motel Williamstown

Williamstown

CNY630 total

includes taxes & fees

Nov 1 - Nov 2

A resort with multiple buildings, a parking area, and a mountainous backdrop.

13. Jiminy Peak Mountain Resort

Hancock

CNY999 total

includes taxes & fees

Oct 28 - Oct 29

A building with a covered parking area and a grassy front yard.

14. Howard Johnson by Wyndham Williamstown

Williamstown

CNY745 total

includes taxes & fees

Oct 28 - Oct 29

A garden with a swing set, a blue chair, and a flower bed.

15. Maple Terrace Motel

Williamstown

CNY737 total

includes taxes & fees

Nov 1 - Nov 2

A kitchen with a countertop, a refrigerator, and a window.

16. The Villager Motel

Williamstown

CNY559 total

includes taxes & fees

Nov 25 - Nov 26

An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Pittsfield

CNY708 total

includes taxes & fees

Nov 24 - Nov 25

A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

18. Rodeway Inn

Adams

CNY477 total

includes taxes & fees

Nov 2 - Nov 3

A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

19. Williamstown Motel

Williamstown

CNY597 total

includes taxes & fees

Nov 8 - Nov 9

An outdoor seating area with Adirondack chairs and potted plants.

20. Cozy Corner Motel

Williamstown

CNY588 total

includes taxes & fees

Nov 2 - Nov 3

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Go beyond your typical stay in Cheshire

Pet friendly

Pool

Top landmarks in Cheshire

St Mary's of the Assumption Church

10.0/10 (1 review)

St Mary's of the Assumption Church is in the heart of Cheshire, so why not stop by during your stay.

See properties

Learn more about Cheshire

Cheshire is well-known for its attractions such as Mount Greylock State Reservation and Cheshire Reservoir.

See all hotels in Cheshire

A lake surrounded by autumn-colored trees and hills.

Check out reviews of Cheshire hotels guests love

Hotel On North

10/10 Excellent

"Very large room and bathroom. Had parking easily accessible, very nice and helpful staff."

Quality Inn Lee - Lenox South

8/10 Good

"Bed was comfortable, breakfast was fine, and it's a generally attractive property. We were in room 125, which was awkwardly laid out. The toilet was mashed up against the sink, and the desk was opposite the foot of the bed, making a traffic bottleneck. I'd guess 126 is the same, but hopefully the rest of the rooms weren't."

Frequently asked questions

How much does a hotel room cost in Cheshire?

You can choose a great hotel in Cheshire from CNY477 with properties to suit all budgets and needs. If you're looking for an affordable hotel in Cheshire that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.

How can I find deals and earn rewards at Cheshire hotels?

Discover great deals on Cheshire hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Cheshire hotels.

Can I book Cheshire hotels with free cancellation?

In order to book a refundable Cheshire hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some of the best hotels in Cheshire for couples?

Enjoy your couple's retreat with a stay at a top-rated Cheshire romantic hotel. Our travelers love Harbour House Inn, a romantic bed & breakfast. Discover more hotels in Cheshire on Hotels.com for couples by using the "Traveler experience" filter in your search and selecting "Adults only" or "Romantic".

What are some of the best Cheshire hotels with free parking?

If you're arriving by car, choosing a great Cheshire hotel with free parking is a plus. Our travelers' favorites include:

Harbour House Inn: A bed & breakfast with an average guest rating of 9.6 out of 10

What are some popular hotels in central Cheshire?

If you're looking for hotels in central Cheshire, check out Harbour House Inn. Travelers love Harbour House Inn for its location, as well as the free full breakfast, wedding services and free parking this bed & breakfast offers.

What accommodations do travelers like in Cheshire?

Guests like Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel and FairBridge Inn Express.

Can I book a refundable hotel in Cheshire?

If you're looking for the flexibility to change your travel plans to Cheshire, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Cheshire if I want a vacation home instead of a traditional hotel?

Browse 5 vacation homes on our site.

What will the weather in Cheshire be like during my vacation?

July and August are typically the warmest months in Cheshire when the average temp is 63°F. January and February are the coldest months when the average temperature is 25°F. July and August are the months with the most rain.

Why should I book my Cheshire hotel with Hotels.com?

There are lots of reasons to book your Cheshire trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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