A lake surrounded by autumn-colored trees and hills.

Find hotels in Cheshire, MA from Rp1.243.172

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Check prices for these dates

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul

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Our top choices for Cheshire hotels

Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is Rp4.546.811
Rp4.805.979 total
includes taxes & fees
30 Jun - 1 Jul
Harbour House Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,000 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is Rp2.136.302
Rp2.386.249 total
includes taxes & fees
30 Jun - 1 Jul
Best Western Plus Berkshire Hills Inn & Suites
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is Rp2.279.678
Rp2.546.401 total
includes taxes & fees
8 Jul - 9 Jul
The Yankee Inn
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,002 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
The price is Rp2.515.236
Rp3.209.896 total
includes taxes & fees
27 Jul - 28 Jul
Berkshire Mountain Lodge
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (613 reviews)
"Very well run property with good amenities and a lovely pool and sitting area. Lots of good attention to detail to make it a desirable place to stay!"
United States
Carolyn
The price is Rp2.311.938
Rp2.582.381 total
includes taxes & fees
29 Jun - 30 Jun
Maple Terrace Motel
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (831 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is Rp1.112.956
Rp1.243.172 total
includes taxes & fees
12 Jul - 13 Jul
FairBridge Inn Express
Room, 1 King Bed, Accessible, Non Smoking (Transfer Shower) | Hypo-allergenic bedding, desk, laptop workspace, blackout curtains

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,000 reviews)
"Spacious and clean room, great location, friendly staff"
United States
Theresa
The price is Rp2.756.224
Rp3.078.703 total
includes taxes & fees
1 Jul - 2 Jul
Hotel Downstreet, an Ascend Collection Hotel
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (140 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is Rp1.873.249
Rp2.971.627 total
includes taxes & fees
30 Jun - 1 Jul
Blooming Inn
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,002 reviews)
"The property was nice and the staff enthusiastic"
United States
Matt
The price is Rp1.668.538
Rp1.863.888 total
includes taxes & fees
2 Jul - 3 Jul
Willows Motel Williamstown
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,001 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is Rp2.664.643
Rp2.976.307 total
includes taxes & fees
7 Jul - 8 Jul
Quality Inn Lee - Lenox South
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (917 reviews)
"Very clean! Friendly staff! Will stop there again!"
United States
Theresa
The price is Rp1.580.720
Rp1.857.974 total
includes taxes & fees
19 Jul - 20 Jul
Cozy Corner Motel
Mountain view

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (914 reviews)
"clean; quiet; good breakfast; as advertised; easy check-in/check out; convenient parking; "
United States
Thomas
The price is Rp1.973.551
Rp2.204.477 total
includes taxes & fees
29 Jun - 30 Jun
Howard Johnson by Wyndham Williamstown
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (472 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is Rp1.209.556
Rp1.354.724 total
includes taxes & fees
1 Jul - 2 Jul
Berkshire Travel Lodge
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1,002 reviews)
"Quiet room. Comfortable bed linens"
United States
Margo
The price is Rp2.278.761
Rp2.545.376 total
includes taxes & fees
30 Jun - 1 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (107 reviews)
"Wonderful stay! Our room was beautiful - clean and cozy. I had a drink at the outside bar - it was lovely. Highly recommend staying here. Itā€™s a hidden gem."
United States
Michelle
The price is Rp2.016.225
Rp2.238.010 total
includes taxes & fees
28 Jun - 29 Jun
Gregory House Country Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (866 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
The price is Rp1.612.801
Rp1.801.519 total
includes taxes & fees
29 Jun - 30 Jun
Berkshire Inn
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
"Clean room and breakfast"
United States
Raphael
The price is Rp2.709.806
Rp3.827.607 total
includes taxes & fees
1 Jul - 2 Jul
The Red Lion Inn
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,002 reviews)
"Great breakfast and coffe is available 24 hours. Nice location to near by restaurants and great view by water."
United States
andrew
The price is Rp3.575.439
Rp3.993.738 total
includes taxes & fees
1 Jul - 2 Jul
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Property amenity

Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
3.0 star property
Williamstown
8.8 out of 10, Excellent, (416 reviews)
"We were very pleased with our stay. The staff at the desk when we checked in and again when we checked out were very accommodating and friendly. "
United States
Susan
The price is Rp3.301.512
Rp3.687.789 total
includes taxes & fees
2 Jul - 3 Jul
Fairfield Inn & Suites by Marriott Williamstown
Exterior

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (312 reviews)
"A beautiful old inn in the heart of a lovely old town."
United States
Linda
The price is Rp2.777.552
Rp3.102.527 total
includes taxes & fees
12 Jul - 13 Jul
The Whitlock
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Cheshire attractions

St Mary's of the Assumption Church

10.0/5 (1 review)
This historic Catholic parish 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

Get away to romantic Cheshire! Enjoy the skiing, hiking and wildlife.

See all hotels in Cheshire
A lake surrounded by autumn-colored trees and hills.

Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The room in lobby were great. The big front porch was actually a nice thing to have, because the fire pit was closed (and the guy worked the front desk at night said he didnā€™t have a key to start it.) The bar was closed. The boutique was closed and there really wasnā€™t anywhere else you could go. We definitely will stay again, but weā€™ll just make sure itā€™s only on the days where we can access all the amenities."
Rose 2-night trip
Posted 16 hours ago
Berkshire Mountain Lodge

More cheap stays in Cheshire

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is Rp1.112.956 per night from 12 Jul to 13 Jul
Rp1.112.956
Rp1.243.172 total
12 Jul - 13 Jul
includes taxes & fees
5.4/10 (831 reviews)

Frequently asked questions

What's the best place to stay in Cheshire?
Located 9.8 mi (15.7 km) from the heart of Cheshire, Hotel Downstreet, an Ascend Collection Hotel is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are The Yankee Inn and Vacation Village in the Berkshires. See all available top hotels, or vacation rentals in Cheshire.
If I need to cancel my hotel reservation in Cheshire, will I receive a refund?
Yes! Most room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
What's the best LGBTQ-friendly place to stay in Cheshire?
Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi. See all available hotels listed as LGBTQ-friendly in Cheshire.
What are some hotels with pools in Cheshire?
Hotel Downstreet, an Ascend Collection Hotel: Features daily, an indoor pool and free self parking. The Yankee Inn and Vacation Village in the Berkshires are two additional hotels that feature an on-site pool. View all hotels with pools in Cheshire.
What is staying in Cheshire like?
Visitors can enjoy all that Cheshire has to offer, including the ski areas, restaurants and lake views. Tourists can also enjoy so much more including its shopping. In Cheshire, there are 6 hotels and other accommodation options to choose from. Find out more about Cheshire.
What is there to see in Cheshire?
A favourite place to visit is Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock in the area. Take a look at what more there is to see and do in Expedia's Cheshire guide.
What's the seasonal weather in Cheshire?
The hottest months are usually July and August, with an average temperature of 17Ā°C, while the coldest months are January and February, with an average of -4Ā°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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