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 .

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June 2026

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July 2026

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Where to stay in Cheshire?

Harbour House Inn

Cheshire

$268 total

includes taxes & fees

Jun 4 - Jun 5

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

Lenox

$118 total

includes taxes & fees

Jun 4 - Jun 5

Berkshire Travel Lodge

Austerlitz

$82 total

includes taxes & fees

Jun 4 - Jun 5

Pleasant Valley Motel West Stockbridge

West Stockbridge

$88 total

includes taxes & fees

Jun 4 - Jun 5

Blooming Inn

Shelburne Falls

$166 total

includes taxes & fees

Jun 4 - Jun 5

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

Howard Johnson by Wyndham Lenox

Lenox

$88 total

includes taxes & fees

Jun 4 - Jun 5

Becket Motel

Becket

$140 total

includes taxes & fees

Jun 4 - Jun 5

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

$123 total

includes taxes & fees

Jun 17 - Jun 18

Shaker Mill Inn

West Stockbridge

$163 total

includes taxes & fees

Jun 4 - Jun 5

Quality Inn Lee - Lenox South

Lee

$130 total

includes taxes & fees

Jun 16 - Jun 17

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Pittsfield

$147 total

includes taxes & fees

Jun 7 - Jun 8

Berkshires Untold

Lenox

$133 total

includes taxes & fees

Jun 4 - Jun 5

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

Berkshire Inn

Pittsfield

$96 total

includes taxes & fees

Jun 4 - Jun 5

Berkshire Mountain Lodge

Pittsfield

$173 total

includes taxes & fees

Jun 4 - Jun 5

Shower, free toiletries, hair dryer, towels

Rodeway Inn

Adams

$80 total

includes taxes & fees

Jun 10 - Jun 11

55-inch LCD TV with digital channels, printers

The Revival House

Adams

$185 total

includes taxes & fees

Jun 16 - Jun 17

The Villager Motel

Williamstown

$99 total

includes taxes & fees

Jun 4 - Jun 5

Hideaway Inn Lenox

Lenox

$173 total

includes taxes & fees

Jun 7 - Jun 8

The Red Lion Inn

Stockbridge

$214 total

includes taxes & fees

Jun 9 - Jun 10

FairBridge Inn Express

Pittsfield

$88 total

includes taxes & fees

Jun 7 - Jun 8

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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

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 Mount Greylock State Reservation Visitor Center.

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

Hampton Inn & Suites Berkshires-Lenox

8/10 Good

"Room was nice, clean, updated, and spacious"

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"I enjoyed relaxing by the firepit. The only thing that could of made it a better stay would be free breakfast or at least coffee and tea. They have a Starbucks and area where you can purchase items but it was more like self serve and pay at reception desk."

Vacation Village in the Berkshires

10/10 Excellent

"While traveling in the area for summer we found Vacation Village. Great jump off point, great amenities, helpful staff, nice set up inside the condo, pots, pans, utensils, glassware, other cooking utensils in good shape. Private decks are a nice touch. Best bargain in the area by far!!! Will be back!"

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent

"I spilled an ENTIRE cup of cocoa I was making for my niece. The clerk on was a very kind, friendly young man named Paul. I have worked as a chef for 30 years, the cocoa went EVERYWHERE. He got a mop bucket , I started cleaning my mess up I just know what its like to walk into a mess!! Left by someone else. Paul said "you dont have to finish, ill do it no problem. He was a VERY kind young man. And he was helpful & he cleaned up the rest of the spill. I think your LUCKY to have such kind helpful employees. Just a side note. The hot tub was wayyy hotter then the thermometer( I think). It was unbearable to sit in it for more then a few minutes. And I LOVE being WARM, but everyone around( 3 others came in to use it but could not sit in it for more then a few seconds. Maybe lower it a bit now that winter is GONE!! Also housekeeping was knocking at our door before it was even 11 am!! Were literally just finishing packing up, and shes knocking. I travel extensively. I know check out is 11am. Unless your in vegas snd pay 30$ for a late check out. Beautiful , clean awesome staff(Paul). Clean!! Well be back!"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

6/10 Okay

"The staff were very polite and helpful. But the property was under construction, so you had to walk over a block to your car and park it or you can do a valet that was never present? From what I was told from other people that were staying there is that the place I’ve been under construction for a couple years now that was not advertise that was going on so it was kind of frustrating."

Frequently asked questions

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.

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