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 Holiday Inn & Suites Pittsfield-Berkshires by IHG .

Where to?

Dates

April 2026

8

May 2026

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Where to stay in Cheshire?

Harbour House Inn

Cheshire

Cozy Cheshire B&B within easy reach of Adams Theater and Mount Greylock.

CNY1,840 total

includes taxes & fees

Apr 9 - Apr 10

Blooming Inn

Shelburne Falls

Charming guesthouse near Glacial Potholes offers free WiFi and winter adventures.

CNY1,054 total

includes taxes & fees

Apr 12 - Apr 13

UU Rowe Camp and Conference Center

Rowe

CNY1,632 total

includes taxes & fees

Apr 9 - Apr 10

12-acre Vacation Rental in the Berkshires!

Charlemont

CNY3,737 total

includes taxes & fees

Apr 10 - Apr 11

Becket Motel

Becket

Contemporary Berkshires retreat with natural surroundings and nearby trails.

CNY1,035 total

includes taxes & fees

Apr 9 - Apr 10

Blue Vista Motor Lodge

North Adams

Tranquil retreat in North Adams with hot tubs and sauna for ultimate relaxation.

CNY1,319 total

includes taxes & fees

Apr 13 - Apr 14

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

Rodeway Inn

Adams

CNY586 total

includes taxes & fees

Apr 15 - Apr 16

The Trail in Adams - Berkshires’ Art Hotel

Adams

CNY1,332 total

includes taxes & fees

Apr 9 - Apr 10

55-inch LCD TV with digital channels, printers

The Revival House

Adams

Tranquil guesthouse in Adams with free breakfast and easy access to local attractions.

CNY1,150 total

includes taxes & fees

Apr 9 - Apr 10

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

CNY975 total

includes taxes & fees

May 5 - May 6

The Porches Inn at Mass MoCA

North Adams

CNY1,450 total

includes taxes & fees

May 7 - May 8

Quality Inn Lee - Lenox South

Lee

A cozy retreat 15 minutes from Tanglewood Music Center with complimentary WiFi.

CNY710 total

includes taxes & fees

Apr 26 - Apr 27

Sunset Inn

Lee

Countryside lodging with a seasonal pool, steps away from Tanglewood Music Center.

CNY767 total

includes taxes & fees

Apr 9 - Apr 10

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

FairBridge Inn Express

Pittsfield

Restful sanctuary in Pittsfield with free WiFi and parking, perfect for skiers.

CNY545 total

includes taxes & fees

Apr 22 - Apr 23

Chambery Inn

Lee

Peaceful countryside retreat with spa treatments just minutes from Tanglewood Music Center.

CNY1,311 total

includes taxes & fees

Apr 9 - Apr 10

Econo Lodge Lee - Great Barrington

Lee

Cozy retreat near Lee Premium Outlets with mini golf and continental breakfast.

CNY515 total

includes taxes & fees

Apr 22 - Apr 23

Devonfield Inn B&B

Lee

Step back from the crowds with a relaxing Berkshires escape next to scenic fairways.

CNY2,522 total

includes taxes & fees

Apr 14 - Apr 15

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Tranquil lakefront escape with stunning sunset views and a 24-hour fitness center.

CNY771 total

includes taxes & fees

Apr 19 - Apr 20

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

South Lee

Berkshire getaway offers indoor and outdoor pools with mountain scenery and cafe.

CNY997 total

includes taxes & fees

Apr 13 - Apr 14

Lakehouse Inn

Lee

Scenic lakeside escape in Lee with kayaking, terrace, and daily full breakfast.

CNY1,159 total

includes taxes & fees

Apr 17 - Apr 18

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Go beyond your typical stay in Cheshire

Apartment

Pet friendly

Top landmarks in Cheshire

St Mary's of the Assumption Church

This historic Catholic church 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

The region around Cheshire is home to attractions such as Mount Greylock State Reservation and St Mary's of the Assumption Church.

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

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Nice staff comfy bed nice views"

Frequently asked questions

How much does a hotel room cost in Cheshire?

You can choose a great hotel in Cheshire from CNY515 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, free parking and wedding services 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 Holiday Inn & Suites Pittsfield-Berkshires by IHG.

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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