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13 Nov - 14 Nov
Tomorrow
14 Nov - 15 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

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Top 10 Cheshire hotels and places to stay

Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
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 Rp4.378.836
Rp4.628.430 total
includes taxes & fees
25 Nov - 26 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
Lee
9.0 out of 10, Wonderful, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is Rp1.833.019
Rp2.047.482 total
includes taxes & fees
3 Dec - 4 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is Rp1.670.028
Rp1.865.421 total
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (798)
"Easy parking, great community spaces, beautiful decor! "
United States
Kerry
The price is Rp1.546.632
Rp1.727.587 total
includes taxes & fees
20 Nov - 21 Nov
Berkshires Untold
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, (954)
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
United States
Stacey
The price is Rp1.472.411
Rp1.644.693 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2134)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
The price is Rp1.639.953
Rp2.014.960 total
includes taxes & fees
14 Nov - 15 Nov
Vacation Village in the Berkshires
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1002)
"Very friendly staff. "
United States
Pamela
The price is Rp2.150.187
Rp3.054.411 total
includes taxes & fees
20 Nov - 21 Nov
The Cornell Inn, Lenox & The Berkshires
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (753)
"Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome. "
United States
Jeff
Berkshire Mountain Lodge
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
South Lee
9.0 out of 10, Wonderful, (781)
"Place was great!"
United States
Benjamin
The price is Rp2.240.078
Rp2.735.537 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (1000)
"Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again."
United States
Tammy
The price is Rp2.411.762
Rp2.693.938 total
includes taxes & fees
11 Dec - 12 Dec
Hotel Downstreet, an Ascend Collection Hotel
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is Rp2.574.418
Rp3.622.540 total
includes taxes & fees
17 Nov - 18 Nov
The Red Lion Inn
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (58)
"Room was far from spotless but overall good and nice breakfast. "
United States
Hannah
The price is Rp1.833.019
Rp2.047.482 total
includes taxes & fees
4 Dec - 5 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Front of property – evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (796)
"Clean room and staff was super friendly"
United States
Yuen
The price is Rp2.226.800
Rp2.487.336 total
includes taxes & fees
20 Nov - 21 Nov
Hotel On North
Front of property – evening/night
The Williams Inn

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (539)
"Lovely place with lovely people. Food is great. "
United States
Deborah
The price is Rp3.290.387
Rp3.675.362 total
includes taxes & fees
20 Nov - 21 Nov
The Williams Inn
Suite, 2 Bedrooms | 2 bedrooms, Frette Italian sheets, premium bedding, down duvets
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 star property
North Adams
9.4 out of 10, Exceptional, (435)
"Charming, nice amenities and convenient to museums, fall foliage, hikes."
United States
Sonya
The price is Rp2.542.656
Rp3.213.676 total
includes taxes & fees
4 Dec - 5 Dec
The Porches Inn at Mass MoCA
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew which was appreciated. We look forward to coming back"
United States
Samuel
Chambery Inn
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

2.5 star property
Pittsfield
5.4 out of 10, (809)
"Room spotless and staff helpful."
United States
William
The price is Rp1.128.397
Rp1.260.419 total
includes taxes & fees
27 Nov - 28 Nov
FairBridge Inn Express
Exterior
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
Williamstown
8.8 out of 10, Excellent, (391)
"We really liked the beautiful fire pit and the warm cup of tea after coming home from dinner."
United States
Kathleen
The price is Rp2.390.531
Rp2.670.223 total
includes taxes & fees
7 Dec - 8 Dec
Fairfield Inn & Suites by Marriott Williamstown
Lobby sitting area
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, (1003)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is Rp1.560.555
Rp1.743.140 total
includes taxes & fees
20 Nov - 21 Nov
Best Western Plus Berkshire Hills Inn & Suites
Exterior detail
Williamstown Motel

Williamstown Motel

2.0 star property
Williamstown
9.4 out of 10, Exceptional, (310)
"It was clean and in a convenient location "
United States
Karen
The price is Rp1.652.706
Rp1.846.072 total
includes taxes & fees
20 Nov - 21 Nov
Williamstown Motel
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

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 local cuisine.

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

Huttopia Berkshires

Huttopia Berkshires

10/10 Excellent
"Healthy food too!"
GEORGINA 2-night trip
Posted 3 weeks ago
Huttopia Berkshires

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 Rp1.318.826 per night from 20 Nov to 21 Nov
Rp1.318.826
Rp1.473.079 total
20 Nov - 21 Nov
includes taxes & fees
7.4/10 Good! (818 reviews)

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 traveller data. This B&B offers free breakfast and free parking. Two other choices for your trip to the area are Vacation Village in the Berkshires and Hotel Downstreet, an Ascend Collection Hotel. 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?
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. Hotel Downstreet, an Ascend Collection Hotel and Berkshire Mountain Lodge 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 5 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 17°C, while the coldest months are January and February, with an average of -4°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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