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 Hotel On North .

Where to?

Dates

June 2026

July 2026

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Where to stay in Cheshire?

Harbour House Inn

Cheshire

CNY1,819 total

includes taxes & fees

May 27 - May 28

Blooming Inn

Shelburne Falls

CNY1,126 total

includes taxes & fees

May 27 - May 28

Becket Motel

Becket

CNY947 total

includes taxes & fees

Jun 2 - Jun 3

Blue Vista Motor Lodge

North Adams

CNY1,315 total

includes taxes & fees

May 27 - May 28

Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, free WiFi, bed sheets

Rodeway Inn

Adams

CNY607 total

includes taxes & fees

May 27 - May 28

The Trail in Adams - Berkshires’ Art Hotel

Adams

CNY1,319 total

includes taxes & fees

May 27 - May 28

55-inch LCD TV with digital channels, printers

The Revival House

Adams

CNY1,179 total

includes taxes & fees

May 27 - May 28

Room, 1 King Bed, Accessible, Non Smoking (Transfer Shower) | Hypo-allergenic bedding, desk, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

North Adams

CNY1,155 total

includes taxes & fees

Jun 1 - Jun 2

The Porches Inn at Mass MoCA

North Adams

CNY1,512 total

includes taxes & fees

May 27 - May 28

Quality Inn Lee - Lenox South

Lee

CNY833 total

includes taxes & fees

Jun 15 - Jun 16

Sunset Inn

Lee

CNY835 total

includes taxes & fees

May 27 - May 28

Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

Pittsfield

CNY539 total

includes taxes & fees

Jun 24 - Jun 25

Chambery Inn

Lee

CNY1,298 total

includes taxes & fees

May 27 - May 28

Econo Lodge Lee - Great Barrington

Lee

CNY539 total

includes taxes & fees

Jun 2 - Jun 3

Devonfield Inn B&B

Lee

CNY2,493 total

includes taxes & fees

Jun 3 - Jun 4

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

CNY880 total

includes taxes & fees

Jun 1 - Jun 2

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

South Lee

CNY1,012 total

includes taxes & fees

Jun 1 - Jun 2

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Pittsfield

CNY1,025 total

includes taxes & fees

May 31 - Jun 1

Hilton Garden Inn Lenox Pittsfield

Pittsfield

CNY1,104 total

includes taxes & fees

Jun 1 - Jun 2

In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Lenox

CNY600 total

includes taxes & fees

May 27 - May 28

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Go beyond your typical stay in Cheshire

Family friendly

Cottage

Top landmarks in Cheshire

St Mary's of the Assumption Church

5.0/5 (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

The region around Cheshire is home to attractions such as Mount Greylock State Reservation and Susan B. Anthony Birthplace Museum.

See all hotels in Cheshire

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

Check out reviews of Cheshire hotels guests love

Berkshire Mountain Lodge

10/10 Excellent

"Clean room. Very well equipped. It is a hidden gem, close to everything. Great experience"

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"The rooms are not at all fancy, but perfect for a family if you want to get away for a few nights. We went with my 3, 4, and 7-year-olds and spent two nights playing in the pool, mini-golfing, and hitting the arcade once or twice. Again, not very high-end, but if you’re with children who love a pool and easy activities, it’s a good choice."

The Yankee Inn

10/10 Excellent

"Had a great stay at the Yankee Inn. I would definitely stay here again. Check in was great and super helpful for what to do and eat in the area. Carl at the bar was the best! Only complaint is that the fitted sheet kept coming up from our king mattress I had the fix them multiple times. Nice indoor pool and hot tub. Close to a lot."

Frequently asked questions

How much does a hotel room cost in Cheshire?

You can choose a great hotel in Cheshire from CNY539 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 9.4 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 Hotel On North.

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.

Keep exploring

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