Photo by Ed Gaffny

Find hotels in Cheshire, MA from AED 277

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1 Nov - 2 Nov
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2 Nov - 3 Nov
Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov

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Compare 1,004 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Exterior
Harbour House Inn
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (52)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is AED 963
AED 1,018 total
includes taxes & fees
3 Nov - 4 Nov
Harbour House Inn
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1004)
"We had a lakeside room which was wonderful!"
United States
Nancy
The price is AED 403
AED 450 total
includes taxes & fees
9 Nov - 10 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (787)
"Easy parking, great community spaces, beautiful decor! "
United States
Kerry
The price is AED 340
AED 380 total
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1026)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is AED 393
AED 439 total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (935)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is AED 378
AED 423 total
includes taxes & fees
3 Nov - 4 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2117)
"Good location; reasonable price; very clean and quiet - would definitely return"
United States
Steven
The price is AED 337
AED 417 total
includes taxes & fees
12 Nov - 13 Nov
Vacation Village in the Berkshires
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
8.8 out of 10, Excellent, (1004)
"Staff was very welcoming and friendly! They provided great tips on restaurants and things to do in are."
United States
Robert
The price is AED 518
AED 579 total
includes taxes & fees
5 Nov - 6 Nov
Hotel Downstreet, an Ascend Collection Hotel
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (742)
"Great stay, perfect "
United States
Lawrence
Berkshire Mountain Lodge
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1002)
"Honestly I just enjoyed being able to relax Play some games in the cute pub and the breakfast was yummy and stuff was inviting and so helpful "
United States
Sandra
The price is AED 473
AED 672 total
includes taxes & fees
2 Nov - 3 Nov
The Cornell Inn, Lenox & The Berkshires
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0 out of 10, Wonderful, (773)
"Lovely spot, great accommodations, friendly staff, and great location."
United States
Joanne
The price is AED 430
AED 531 total
includes taxes & fees
13 Nov - 14 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (56)
"Bright new hotel with very friendly and helpful staff. "
United States
Mary
The price is AED 434
AED 485 total
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Outdoor pool, sun loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1026)
"Food was great!"
United States
Emily
The price is AED 516
AED 740 total
includes taxes & fees
16 Nov - 17 Nov
The Red Lion Inn
Front of property - evening/night
The Williams Inn
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (532)
"Great stay"
United States
SIDNEY
The price is AED 724
AED 809 total
includes taxes & fees
17 Nov - 18 Nov
The Williams Inn
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
FairBridge Inn Express
2.5 star property
5.4 out of 10, (803)
"Good service and people"
United States
Jerod
The price is AED 248
AED 277 total
includes taxes & fees
16 Nov - 17 Nov
FairBridge Inn Express
Front of property - evening/night
Hotel On North
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (788)
"Clean modern place in town, good value. Room on street side was a little noisy at night, ask for back room if light sleeper. Restaurant was not good value. "
United States
Michael
The price is AED 490
AED 547 total
includes taxes & fees
16 Nov - 17 Nov
Hotel On North
Suite, 2 Bedrooms | 2 bedrooms, Frette Italian sheets, premium bedding, down comforters
The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCA
3.5 star property
9.4 out of 10, Exceptional, (432)
"Excellent place! "
United States
Francisco
The price is AED 590
AED 741 total
includes taxes & fees
1 Dec - 2 Dec
The Porches Inn at Mass MoCA
Front of property
The Constance by the Lenox Collection
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very Good, (558)
"I liked the old world decor and the living room area to chill out in "
United States
Jelena
The Constance by the Lenox Collection
Exterior detail
Williamstown Motel
Williamstown Motel
2.0 star property
9.4 out of 10, Exceptional, (309)
"It was clean and in a convenient location "
United States
Karen
The price is AED 338
AED 378 total
includes taxes & fees
2 Nov - 3 Nov
Williamstown Motel
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
4.0 star property
8.8 out of 10, Excellent, (335)
"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"
United States
Candee
The price is AED 415
AED 464 total
includes taxes & fees
2 Nov - 3 Nov
The Central Downtown Inn & Suites
Exterior
Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (390)
"We really liked the beautiful fire pit and the warm cup of tea after coming home from dinner."
United States
Kathleen
The price is AED 577
AED 644 total
includes taxes & fees
6 Nov - 7 Nov
Fairfield Inn & Suites by Marriott Williamstown
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

St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views, or seek out its ski slopes.
See properties

Learn more about Cheshire

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

See all hotels in Cheshire
The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..
Photo by Ed Gaffny
Open Photo by Ed Gaffny

Top Cheshire Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Clean room and very friendly staff. "
Michael 2-night trip
Posted 2 days ago
The Red Lion Inn

More cheap stays in Cheshire

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is AED 290 per night from Nov 2 to Nov 3
AED 290
AED 324 total
2 Nov - 3 Nov
includes taxes & fees
7.4/10 Good! (815 reviews)

Hotels in Cheshire with star-rating

Frequently asked questions

What's the best place to stay in Cheshire?
Harbour House Inn is one of the top choices for your stay based on our traveler data. This B&B offers free breakfast and free parking. Other good options for your stay in the area are Vacation Village in the Berkshires and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Cheshire.
What are some of the best vacation rentals in Cheshire?
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox: This vacation home rental outside Cheshire is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Cheshire.
If I need to cancel my hotel reservation in Cheshire, will I receive a refund?
Yes! Most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
Where can I learn more about changing or cancelling my trip to Cheshire?
To find more details about updating your trip to Cheshire or cancelling it, click here.
What is the favorite LGBTQ-friendly accommodation in Cheshire?
Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi.
What are some hotels with pools in Cheshire?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG are two additional hotels with an onsite pool. View all hotels with pools in Cheshire.
What is the best hotel near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
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 5 hotels and other accommodations to choose from. Find out more about Cheshire.
What are the top places to visit in Cheshire?
A favorite place to visit is Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock in the area. Check out what more to see and do in Expedia's Cheshire guide.
What's the seasonal weather like in Cheshire?
The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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