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Recommended hotels in Cheshire

Bed & Breakfast in Cheshire

Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (53)
"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 790
AED 835 total
includes taxes & fees
7 Jan - 8 January 2026
Harbour House Inn

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (1001)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is AED 346
AED 387 total
includes taxes & fees
5 Jan - 6 January 2026
Best Western Plus Berkshire Hills Inn & Suites

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is AED 481
AED 537 total
includes taxes & fees
17 Dec - 18 Dec
Element Lenox Berkshires

Bed & Breakfast in West Stockbridge

Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is AED 396
AED 435 total
includes taxes & fees
14 Dec - 15 Dec
Shaker Mill Inn

Guesthouse in Shelburne Falls

Blooming Inn
3.0 star property
9.2 out of 10, Wonderful, (124)
"Excellent! Really fun space with beautiful objects all around you. One of a kind, well run, seamless experience. "
United States
Ben
The price is AED 240
AED 449 total
includes taxes & fees
15 Dec - 16 Dec
Blooming Inn

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
9.2 out of 10, Wonderful, (1000)
"Great stay there!! Very friendly staff"
United States
Ann
The price is AED 275
AED 307 total
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
2.0 star property
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is AED 290
AED 324 total
includes taxes & fees
21 Dec - 22 Dec
Howard Johnson by Wyndham Lenox

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is AED 398
AED 444 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
8.8 out of 10, Excellent, (1001)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is AED 393
AED 439 total
includes taxes & fees
20 Dec - 21 Dec
Hotel Downstreet, an Ascend Collection Hotel

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, (984)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AED 340
AED 380 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Motel in Williamstown

Cozy Corner Motel
2.0 star property
9.2 out of 10, Wonderful, (884)
"Clean, Great Staff, Quiet"
United States
john
The price is AED 274
AED 324 total
includes taxes & fees
14 Dec - 15 Dec
Cozy Corner Motel

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
8.4 out of 10, Very Good, (1001)
"Clean room and good breakfast "
United States
Kelly
The price is AED 328
AED 366 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Lee - Lenox South

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, (1000)
"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 AED 372
AED 415 total
includes taxes & fees
21 Dec - 22 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Motel in Williamstown

The Villager Motel
2.0 star property
8.8 out of 10, Excellent, (764)
"It's very good for stay over"
United States
Frances
The price is AED 253
AED 283 total
includes taxes & fees
14 Dec - 15 Dec
The Villager Motel

Motel in New Ashford

The Springs Motel
2.0 star property
9.2 out of 10, Wonderful, (87)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is AED 399
AED 438 total
includes taxes & fees
12 Dec - 13 Dec
The Springs Motel
10.0 out of 10, Exceptional, (119)
"We had a great visit! Easy to access, clean and comfortable. The studio had everything we needed!Great host!"
United States
Marina G.
The price is AED 349
AED 574 total
includes taxes & fees
15 Dec - 16 Dec
In town, newly remodeled studio with private balcony

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is AED 379
AED 423 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn & Suites Berkshires-Lenox

Lodge in Pittsfield

Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (787)
"This place is so peaceful and the staff is always helpful "
United States
Leona
The price is AED 362
AED 487 total
includes taxes & fees
8 Jan - 9 January 2026
Berkshire Mountain Lodge
2.0 star property
6.8 out of 10, (1001)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is AED 193
AED 212 total
includes taxes & fees
10 Jan - 11 January 2026
Pleasant Valley Motel West Stockbridge

Motel in Williamstown

Williamstown Motel
2.0 star property
9.4 out of 10, Exceptional, (314)
"Was upgraded to a larger room for no special reason. Very nice proprietor. For budget priced accommodations, this is an excellent value. Would definitely stay here again if I am in the area."
United States
DAVID
The price is AED 327
AED 365 total
includes taxes & fees
14 Dec - 15 Dec
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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Top Cheshire Hotel Reviews

Frequently asked questions

What can I look forward to during my aparthotel stay in Cheshire?
When you choose an aparthotel or serviced apartment in Cheshire, expect to be more centrally situated. You can also come to Cheshire for its ski areas and restaurants.
What are some top aparthotels in Cheshire?
Located 6.5 mi (10.5 km) from Cheshire, Mountainside Condo Ski In Ski Out is a favorite aparthotel and the apartment features a kitchenette and a fireplace along with hotel amenities like a fitness center. In the area, a couple of other top aparthotels to consider are The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook and The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook.
How many aparthotels are available in Cheshire?
On Expedia, you'll find 5 hotels and other accommodations in Cheshire. Though you won't find many aparthotels, we can help you locate places to stay that are similar such as a condo or apartment.
What should I see and do in Cheshire?
Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Mount Greylock State Reservation. In the larger area, you'll find St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.
What is an aparthotel?
An aparthotel or serviced apartment features the privacy and space of an apartment and amenities you might expect at a traditional hotel. Live like a local when you return to your apartment-like space, often located centrally in Cheshire. Enjoy making home-cooked meals in a fully-equipped kitchen and having more space to spread out while you're in town.