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Check prices for these dates

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12 Apr - 13 Apr
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13 Apr - 14 Apr
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17 Apr - 19 Apr
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24 Apr - 26 Apr

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Our top choices for Cheshire hotels

Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is ฿8,128
฿8,591 total
includes taxes & fees
14 Apr - 15 Apr
Harbour House Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (895 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is ฿2,514
฿2,808 total
includes taxes & fees
15 Apr - 16 Apr
Berkshires Untold
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (897 reviews)
"We love Cozy Corner. It's a snug, safe, well-maintained, home away from home. Love the ample breakfast and the genuine welcome we receive every time."
United States
Ann
The price is ฿2,537
฿2,990 total
includes taxes & fees
16 Apr - 17 Apr
Cozy Corner Motel
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (784 reviews)
"very clean, up to day, no thrills overnighter. perfect stop from NYC to VT skiing"
United States
Martin
The price is ฿2,531
฿2,827 total
includes taxes & fees
16 Apr - 17 Apr
The Villager Motel
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
The price is ฿3,229
฿5,177 total
includes taxes & fees
14 Apr - 15 Apr
Blooming Inn
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (28 reviews)
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
The price is ฿4,808
฿5,370 total
includes taxes & fees
14 Apr - 15 Apr
The Revival House
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (846 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is ฿2,531
฿2,827 total
includes taxes & fees
14 Apr - 15 Apr
Howard Johnson by Wyndham Lenox
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

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, (1,003 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is ฿3,546
฿3,961 total
includes taxes & fees
16 Apr - 17 Apr
Best Western Plus Berkshire Hills Inn & Suites
Desk, laptop workspace, blackout curtains, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is ฿2,278
฿2,499 total
includes taxes & fees
14 Apr - 15 Apr
Pleasant Valley Motel West Stockbridge
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is ฿3,748
฿4,112 total
includes taxes & fees
14 Apr - 15 Apr
Shaker Mill Inn
Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, free WiFi, bed sheets

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (240 reviews)
"Found dead flies in the beds and the sheets were stained. I would not expect much from an inexpensive room but I do expect it to be clean."
United States
Heidi
The price is ฿2,451
฿2,738 total
includes taxes & fees
19 Apr - 20 Apr
Rodeway Inn
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (905 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is ฿2,775
฿3,816 total
includes taxes & fees
12 May - 13 May
Berkshire Mountain Lodge
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is ฿4,709
฿5,260 total
includes taxes & fees
19 Apr - 20 Apr
Element Lenox Berkshires
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,001 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is ฿2,968
฿3,316 total
includes taxes & fees
26 Apr - 27 Apr
Quality Inn Lee - Lenox South
Courtyard

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (95 reviews)
"Great quaint place. Great staff and very clean. "
United States
Janelle
The price is ฿3,893
฿4,270 total
includes taxes & fees
29 Apr - 30 Apr
The Springs Motel
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
"Comfortable stay "
United States
Paul
The price is ฿3,364
฿4,831 total
includes taxes & fees
14 Apr - 15 Apr
Becket Motel
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (600 reviews)
"Staff is very nice and the rooms are always clean!"
United States
Peter
The price is ฿3,332
฿3,722 total
includes taxes & fees
21 Apr - 22 Apr
Maple Terrace Motel
Lake

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, (1,002 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is ฿3,242
฿3,621 total
includes taxes & fees
30 Apr - 1 May
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
The price is ฿4,384
฿4,897 total
includes taxes & fees
15 Apr - 16 Apr
Hideaway Inn Lenox
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (88 reviews)
"New hotel clean and nice. Heated pool and hot tub a bonus. Timely breakfast for early departures- great on demand coffee. Added bonus they have a car charger."
United States
Charline
The price is ฿3,780
฿4,223 total
includes taxes & fees
16 Apr - 17 Apr
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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
An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Top Cheshire Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Very nice experience at this historic hotel. Very clean rooms. My one complaint is that we had a room with a fireplace (which was more expensive than a comparable room without a fireplace) but it was just plastic logs with lights. Quite a disappointment when expecting a propane fireplace. "
Sheila 1-night trip
Posted 2 hours ago
The Red Lion Inn

More cheap stays in Cheshire

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is ฿2,531 per night from 14 Apr to 15 Apr
฿2,531
฿2,827 total
14 Apr - 15 Apr
includes taxes & fees
7.6/10 Good! (846 reviews)

Frequently asked questions

What's the best place to stay in Cheshire?
Located 6.5 mi (10.5 km) from the heart of Cheshire, Vacation Village in the Berkshires is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Hotel Downstreet, an Ascend Collection Hotel and Berkshire Mountain Lodge. 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: Features 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 6 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 Susan B. Anthony Birthplace Museum 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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