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Cheshire Hotels

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Check Cheshire hotel prices

Tonight
25 Nov - 26 Nov
Tomorrow night
26 Nov - 27 Nov
This weekend
29 Nov - 1 Dec
Next weekend
6 Dec - 8 Dec

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Top 10 trending Cheshire hotels

The Williams Inn
Front of property – evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (371)
"A lovely hotel in close proximity to the Clark. Highly recommended!"
The price is €208
includes taxes & fees
3 Dec - 4 Dec
The Williams Inn
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is €187
includes taxes & fees
3 Dec - 4 Dec
Vacation Village in the Berkshires
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (442)
"Looking forward to our weekend here. So far this establishment is fabulous! "
The price is €135
includes taxes & fees
27 Nov - 28 Nov
Life House Berkshires
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1008)
"Staff was very nice, friendly and accommodating. The room was nice, clean, comfortable and spacious. "
The price is €95
includes taxes & fees
1 Dec - 2 Dec
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Indoor pool

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very good, (682)
"The restaurant is as great!"
The price is €101
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is €157
includes taxes & fees
27 Nov - 28 Nov
Jiminy Peak Mountain Resort
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (650)
"Very nice!"
The price is €155
includes taxes & fees
1 Dec - 2 Dec
Hotel On North
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1044)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "
The price is €124
includes taxes & fees
9 Dec - 10 Dec
Hotel Downstreet
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (411)
"Loved our room. Very clean"
The price is €196
includes taxes & fees
3 Dec - 4 Dec
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1030)
"The stay was ok but the key to our door was broken and the receptionist promised to change it but she didnt so we have no key to properly enter the room.I also told another receptionist and still the same. "
The price is €126
includes taxes & fees
2 Dec - 3 Dec
Hampton Inn & Suites Berkshires-Lenox
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.4 out of 10, Very good, (1010)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"
The price is €96
includes taxes & fees
2 Dec - 3 Dec
Best Western Plus Berkshire Hills Inn & Suites
Courtyard by Marriott Lenox Berkshires
Indoor pool

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (533)
"Nice, friendly staff. large lobby area with multiple seating areas. Coffee over priced. "
The price is €131
includes taxes & fees
11 Dec - 12 Dec
Courtyard by Marriott Lenox Berkshires
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (747)
"Nice area "
The price is €92
includes taxes & fees
1 Dec - 2 Dec
Berkshire Inn
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (369)
"The Porches is always a treasure in the midst of chain hotels. Just the right balance of "old school" with contemporary charm. It's the place to stay in North Adams if you can get in!!"
The price is €196
includes taxes & fees
3 Dec - 4 Dec
The Porches Inn at Mass MoCA
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (678)
"I don’t know so many complaints. Bed was good, clean. Plenty of park. Provided what we paid for and was expecting. "
The price is €84
includes taxes & fees
1 Dec - 2 Dec
FairBridge Inn Express
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (701)
"It served our needs"
The price is €84
includes taxes & fees
1 Dec - 2 Dec
Howard Johnson by Wyndham Lenox
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (618)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions. "
The price is €146
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Lenox Pittsfield
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (824)
"Very nice, very convenient."
The price is €107
includes taxes & fees
1 Dec - 2 Dec
Howard Johnson by Wyndham Williamstown
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (308)
"It was a wonderful stay, the staff was ready to help and it was a quiet clean place to do work and also go enjoy the beautiful town of Williamstown"
The price is €143
includes taxes & fees
16 Dec - 17 Dec
Fairfield Inn & Suites by Marriott Williamstown
1896 House Country Inn & Motels
Exterior

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (404)
"Excellent experience for the price. Lovely area next to creek. Helpful staff"
The price is €82
includes taxes & fees
4 Dec - 5 Dec
1896 House Country Inn & Motels
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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Frequently asked questions

What's the best place to stay in Cheshire?

Located 20.8 mi (33.4 km) from the heart of Cheshire, The Red Lion Inn is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Life House Berkshires and The Yankee, Trademark Collection by Wyndham. See all available top hotels, or vacation rentals in Cheshire.

What are some of the best holiday rentals that Cheshire has to offer?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Cheshire is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind. See all 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?

Modern Berkshires home + private pool: Provides TVs, an outdoor pool and air conditioning. Vacation Village in the Berkshires and Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel are two additional hotels that feature an on-site pool.

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 3 hotels and other accommodation options to choose from. Find out more about Cheshire.

What is there to see in Cheshire?

A couple of favourite places to visit are Mount Greylock State Reservation and St Mary's of the Assumption Church. 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.