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Cheshire Hotels

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Check Cheshire hotel prices

Tonight
29 Dec - 30 Dec
Tomorrow night
30 Dec - 31 Dec
Next weekend
3 Jan - 5 Jan

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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, (395)
"Loved everything about our stay and we will be back. I haven’t received a receipt yet so please send one. "
The price is €173
includes taxes & fees
2 Jan - 3 Jan 2025
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, (1750)
"Nice and quiet family get a way"
The price is €207
includes taxes & fees
1 Jan - 2 Jan 2025
Vacation Village in the Berkshires
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (460)
"Really loved the design and comfort. The lobby was exquisite, and the rooms were gorgeous. "
The price is €95
includes taxes & fees
5 Jan - 6 Jan 2025
Life House Berkshires
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, (708)
"The service is so good "
The price is €106
includes taxes & fees
5 Jan - 6 Jan 2025
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1003)
"Very nice stay with friendly and helpful staff. Nice breakfast in the morning. Comfortable room."
The price is €104
includes taxes & fees
5 Jan - 6 Jan 2025
The Yankee, Trademark Collection by Wyndham
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (668)
"Very large room with a huge desk and two arm chairs. The bathroom was nice with a large walk-in shower and a rain shower head. My room faced North street, so I noticed the noise from the road, but most wouldn’t notice. Very pleased"
The price is €139
includes taxes & fees
2 Jan - 3 Jan 2025
Hotel On North
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (921)
"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 €199
includes taxes & fees
1 Jan - 2 Jan 2025
Jiminy Peak Mountain Resort
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1003)
"Stayed for a weekend wedding and it was a great location. Room was large "
The price is €124
includes taxes & fees
12 Jan - 13 Jan 2025
Hotel Downstreet
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1005)
"nice & quiet at night with a good solid breakfast in the morning"
The price is €136
includes taxes & fees
5 Jan - 6 Jan 2025
Hampton Inn & Suites Berkshires-Lenox
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (543)
"Staff were pleasant and helpful. Limited menu at the hotel's bistro, but two restaurants across the busy road. Pool is much smaller than it looks in the photo and hot tub was too hot. Rooms somewhat small but well laid-out."
The price is €149
includes taxes & fees
23 Jan - 24 Jan 2025
Courtyard by Marriott Lenox Berkshires
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (417)
"Good"
The price is €196
includes taxes & fees
1 Jan - 2 Jan 2025
Berkshire Mountain Lodge
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1003)
"Super friendly front desk staffs. We had wonderful time. "
The price is €101
includes taxes & fees
5 Jan - 6 Jan 2025
Best Western Plus Berkshire Hills Inn & Suites
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (371)
"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 €165
includes taxes & fees
28 Jan - 29 Jan 2025
The Porches Inn at Mass MoCA
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (622)
"We enjoyed our overnight stay very much. It was conveniently located near all of our pre-holiday destinations. We will definitely be back!"
The price is €149
includes taxes & fees
12 Jan - 13 Jan 2025
Hilton Garden Inn Lenox Pittsfield
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (311)
"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 €163
includes taxes & fees
12 Jan - 13 Jan 2025
Fairfield Inn & Suites by Marriott Williamstown
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (755)
"This is a nice motel, though there is no continental breakfast. There is a pot of coffee made at 7am. The rooms are clean and updated, the mattress is good, airconditioner in back wall, simple round thermostat for hot water radiator heating, mini-fridge is compressor type, microwave."
The price is €92
includes taxes & fees
30 Dec - 31 Dec
Berkshire Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (687)
"Nice room for price close by to everything fulfilled my needs"
The price is €74
includes taxes & fees
30 Dec - 31 Dec
FairBridge Inn Express
1896 House Country Inn & Motels
Exterior

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (406)
"It’s unique historical property. The front desk allowed us to check in three hours early due to it’s a snowy day. We had a lovely thanksgiving dinner in the restaurant belongs to the hotel. "
The price is €82
includes taxes & fees
31 Dec - 1 Jan 2025
1896 House Country Inn & Motels
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (704)
"The room was clean and spacious. The parking lot still had a lot of snow and especially ice"
The price is €85
includes taxes & fees
1 Jan - 2 Jan 2025
Howard Johnson by Wyndham Lenox
Club Wyndham Bentley Brook
Exterior

Club Wyndham Bentley Brook

3.0 star property
9.2 out of 10, Wonderful, (493)
"Amazing location and service!"
Club Wyndham Bentley Brook
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 9.8 mi (15.8 km) from the heart of Cheshire, Hotel Downstreet is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are The Yankee, Trademark Collection by Wyndham and Life House Berkshires. 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.