Hotels in Cheshire

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Top 5 hotels in Cheshire at a glance

Harbour House Inn — 3.5-star hotel in Cheshire. Guest rating: 9.4/10 — Exceptional.
The Yankee Inn — 2.5-star hotel in Lenox. Guest rating: 9.2/10 — Wonderful.
The Trail in Adams - Berkshires’ Art Hotel — 2.5-star hotel in Adams. Guest rating: 9.0/10 — Wonderful.
Hotel Downstreet, an Ascend Collection Hotel — 3-star hotel in North Adams. Guest rating: 8.8/10 — Excellent.
The Revival House — 3-star hotel in Adams. Guest rating: 9.0/10 — Wonderful.

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 comfort, location and traveler experience. Last updated on August 26, 2026.

Harbour House Inn

Cheshire

CNY1,705

CNY1,802 total

includes taxes & fees

Aug 27 - Aug 28

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

Superior Room, 1 King Bed, Jetted Tub | Desk, laptop workspace, iron/ironing board, WiFi (free)

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

Lenox

CNY1,028

CNY1,149 total

includes taxes & fees

Sep 13 - Sep 14

1 bedroom, premium bedding, desk, WiFi (free)

28-inch TV with digital channels, Netflix, books

The Trail in Adams - Berkshires’ Art Hotel

Adams

CNY1,344

CNY1,502 total

includes taxes & fees

Sep 16 - Sep 17

Hypo-allergenic bedding available, desk, laptop workspace

Hotel Downstreet, an Ascend Collection Hotel

North Adams

CNY1,000

CNY1,117 total

includes taxes & fees

Sep 2 - Sep 3

55-inch LCD TV with digital channels, printers

Romantic Room, 1 King Bed (Room 4) | Desk, iron/ironing board (on request), WiFi (free)

The Revival House

Adams

CNY1,113

CNY1,243 total

includes taxes & fees

Sep 20 - Sep 21

Honeymoon Suite, 1 King Bed, Patio | Laptop workspace, WiFi (free), individually decorated

Cabin, 3 Bedrooms, Mountainside | Living area | Smart TV

The Springs Motel

New Ashford

CNY824

CNY904 total

includes taxes & fees

Aug 31 - Sep 1

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

CNY800

CNY893 total

includes taxes & fees

Sep 24 - Sep 25

Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

Williamstown

CNY584

CNY726 total

includes taxes & fees

Aug 31 - Sep 1

Double Room, Accessible | In-room safe, desk, WiFi (free), bed sheets

Blue Vista Motor Lodge

North Adams

CNY1,439

CNY1,521 total

includes taxes & fees

Aug 31 - Sep 1

Deluxe Triple Room | Minibar, laptop workspace, blackout drapes, iron/ironing board

Berkshire Valley Inn

Williamstown

CNY1,119

CNY1,250 total

includes taxes & fees

Sep 7 - Sep 8

Hilton Garden Inn Lenox Pittsfield

Pittsfield

CNY983

CNY1,098 total

includes taxes & fees

Sep 13 - Sep 14

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

Maple Terrace Motel

Williamstown

CNY840

CNY939 total

includes taxes & fees

Sep 9 - Sep 10

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

Pittsfield

CNY800

CNY893 total

includes taxes & fees

Sep 24 - Sep 25

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

CNY772

CNY862 total

includes taxes & fees

Sep 20 - Sep 21

Library Suite, 1 King Bed | Premium bedding, minibar, in-room safe, desk

Hotel On North

Pittsfield

CNY1,203

CNY1,344 total

includes taxes & fees

Sep 7 - Sep 8

Howard Johnson by Wyndham Williamstown

Williamstown

CNY739

CNY826 total

includes taxes & fees

Aug 27 - Aug 28

Fairfield Inn & Suites by Marriott Williamstown

Williamstown

CNY1,236

CNY1,381 total

includes taxes & fees

Sep 20 - Sep 21

The Williams Inn

Williamstown

CNY1,765

CNY1,972 total

includes taxes & fees

Sep 14 - Sep 15

Standard Room, 1 Queen Bed, Non Smoking | Blackout drapes, iron/ironing board (on request), WiFi (free)

Cozy Corner Motel

Williamstown

CNY593

CNY697 total

includes taxes & fees

Sep 9 - Sep 10

Willows Motel Williamstown

Williamstown

CNY696

CNY777 total

includes taxes & fees

Aug 27 - Aug 28

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Go beyond your typical stay in Cheshire

Pet friendly

Pool

Family friendly

Hot tub

Cottage

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

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Helpful staff, clean large suite with 2 beds and baths. Enjoyed the activity center and all it had to offer."

The Yankee Inn

10/10 Excellent

"Charming hotel with a wonderful breakfast and two lovely pools, plus a nature walk to a lake. The staff were great, really nice and helpful."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Nice place"

The Red Lion Inn

10/10 Excellent

"The room was very nice, super clean. Sitting on the porch is what we love most. Food was good, drinks a bit pricey..but when you're on vacation it hardly matters. The pool was nice, the hot tub too. A pleasant stay in a historic inn. It's the berkshires so its beautiful"

Berkshire Mountain Lodge

10/10 Excellent

"We were very happy with how large the rooms were and it felt like you were in an apartment great location and very clean excellent customer service at the front desk"

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"Fine place to stay in the Lenox area."

Quality Inn Lee - Lenox South

8/10 Good

"Clean room, surprisingly comfortable bed. Convenient, functional, for a short stay."

FairBridge Inn Express

10/10 Excellent

"It was very nice and everyone was extremely helpful"

Howard Johnson by Wyndham Lenox

8/10 Good

"Room was clean and comfortable. Always nice to have a frig and microwave."

Frequently asked questions

How much does a hotel room cost in Cheshire?

You can choose a great hotel in Cheshire from CNY466 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, FairBridge Inn Express and Hotel Downstreet, an Ascend Collection Hotel.

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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