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Check Cheshire hotel prices

Tonight
9 Jan - 10 Jan
Tomorrow night
10 Jan - 11 Jan
This weekend
10 Jan - 12 Jan
Next weekend
17 Jan - 19 Jan

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

The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (402)
"Great! Love the coffee bar on each floor. "
The price is AED 674
AED 753 total
includes taxes & fees
12 Jan - 13 Jan
The Williams Inn
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1752)
"So enjoyed this property and all the staff was always there to help in anyway!"
The price is AED 689
AED 792 total
includes taxes & fees
14 Jan - 15 Jan
Vacation Village in the Berkshires
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (470)
"Easy parking, quiet place and nice staff"
The price is AED 326
AED 364 total
includes taxes & fees
22 Jan - 23 Jan
Life House Berkshires
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very Good, (717)
"Good location and helpful staff. Restaurant on premises was very good (not hotel) which was nice. "
The price is AED 375
AED 418 total
includes taxes & fees
11 Jan - 12 Jan
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, (1002)
"Friendly, helpful management & staff. Excellent breakfast, made to order omelettes. Quiet. great pool & jacuzzi. Clean."
The price is AED 378
AED 422 total
includes taxes & fees
20 Jan - 21 Jan
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, (672)
"Historic building nicely renovated "
The price is AED 477
AED 533 total
includes taxes & fees
12 Jan - 13 Jan
Hotel On North
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (922)
"It’s challenging to read the reviews and know what to expect for this hotel. One main reason for that is because each unit is owned by different owners. Some units may have been renovated more recently than other units. I booked 3 rooms. One unit had an old electric stove with coils while the other had a newer electric stove. 1 had a toaster oven while the others did not. We brought food to cook, but kept it simple because we didn’t know what cooking pots and utensils would be available. One...
The price is AED 694
AED 762 total
includes taxes & fees
14 Jan - 15 Jan
Jiminy Peak Mountain Resort
Hotel Downstreet
Exterior

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1000)
"The Hotel Downstreet is the best hotel. We always enjoy our stay here and never hesitate to stay again when in the area. "
The price is AED 426
AED 476 total
includes taxes & fees
22 Jan - 23 Jan
Hotel Downstreet
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Nice pool and breakfast. Exactly like my previous experiences at Hampton Inn except this was probably the the fewest people I've encountered when staying with this chain. It was very quiet. Had the pool to ourselves for an hour."
The price is AED 465
AED 520 total
includes taxes & fees
21 Jan - 22 Jan
Hampton Inn & Suites Berkshires-Lenox
Courtyard by Marriott Lenox Berkshires
Exterior

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 AED 511
AED 570 total
includes taxes & fees
27 Jan - 28 Jan
Courtyard by Marriott Lenox Berkshires
Berkshire Mountain Lodge
Exterior

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (417)
"Good"
The price is AED 606
AED 750 total
includes taxes & fees
14 Jan - 15 Jan
Berkshire Mountain Lodge
Best Western Plus Berkshire Hills Inn & Suites
Exterior

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"The hotel was very clean; the staff were friendly and helpful; bedding and towels were good quality. Breakfast choices were decent. Only two small complaints - sound proofing could be improved as we heard the crying baby and dog from the room next to us much of the night. Also, three pillows on each bed, but they were all very hard - no give at all."
The price is AED 346
AED 387 total
includes taxes & fees
20 Jan - 21 Jan
Best Western Plus Berkshire Hills Inn & Suites
The Porches Inn at Mass MoCA
Outdoor pool

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (372)
"Our favorite place to stay. Rooms, amenities, service and breakfast are top notch. So close to great museums and restaurants. "
The price is AED 528
AED 651 total
includes taxes & fees
9 Feb - 10 Feb
The Porches Inn at Mass MoCA
Hilton Garden Inn Lenox Pittsfield
Exterior

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (623)
"Excellent place "
The price is AED 511
AED 571 total
includes taxes & fees
12 Jan - 13 Jan
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, (312)
"Stay was solid "
The price is AED 492
AED 550 total
includes taxes & fees
14 Jan - 15 Jan
Fairfield Inn & Suites by Marriott Williamstown
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (759)
"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 AED 316
AED 353 total
includes taxes & fees
14 Jan - 15 Jan
Berkshire Inn
FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (695)
"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 AED 253
AED 283 total
includes taxes & fees
12 Jan - 13 Jan
FairBridge Inn Express
1896 House Country Inn & Motels
Exterior

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (407)
"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 AED 316
AED 353 total
includes taxes & fees
21 Jan - 22 Jan
1896 House Country Inn & Motels
Howard Johnson by Wyndham Lenox
Outdoor pool

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (705)
"The room was clean and spacious. The parking lot still had a lot of snow and especially ice"
The price is AED 290
AED 324 total
includes taxes & fees
12 Jan - 13 Jan
Howard Johnson by Wyndham Lenox
Club Wyndham Bentley Brook
Exterior

Club Wyndham Bentley Brook

3.0 star property
9.2 out of 10, Wonderful, (496)
"Better than expected! No complaints! Very impressed with the staff! Every staff member we encountered was kind, professional, helpful and pleasant! From the front desk employees, to the men who were taking care of the pool, to the staff shoveling snow and salting, to the women we observed pushing these heavy wagons to the gentleman responding to a service call who helped us find our way around….very impressive! It was our first time here and we’re discussing our next trip back with friends!...
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 traveler data. Other good options for your stay in 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 vacation rentals in Cheshire?

Berkshire Village Carriage House - Super Private!!: This vacation home rental outside of Cheshire is located in the mountains and has a garden, a barbecue grill, 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 the 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 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 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 3 hotels and other accommodations to choose from. Find out more about Cheshire.

What are the top places to visit in Cheshire?

A couple of favorite 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. 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.