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Cheshire Hotels

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Check Cheshire hotel prices

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May 2 - May 3
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May 3 - May 4
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May 3 - May 5
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May 10 - May 12

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Top 10 trending Cheshire hotels

Front of property - evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (293)
"I love everything about this property!"
The price is P 16,080
per night
May 27 - May 28
The Williams Inn
Exterior detail
Maple Terrace Motel
2.5 star property
9.6 out of 10, Exceptional, (503)
"Arrived late after office closed. Easy arrangements for check in made with no issues. Light in room was on to welcome me. Room was very clean with nice appointments of water, coffee, tea, chocolates. "
The price is P 6,072
per night
May 5 - May 6
Maple Terrace Motel
Exterior
The Porches Inn
3.5 star property
9.4 out of 10, Exceptional, (340)
"Pool!!!"
The price is P 10,929
per night
May 5 - May 6
The Porches Inn
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Lobby
Life House Berkshires
3.5 star property
9.2 out of 10, Wonderful, (232)
"Very accommodating and friendly staff. Coffee in the morning was excellent. "
The price is P 5,720
per night
May 8 - May 9
Life House Berkshires
Indoor pool
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (506)
"Property was clean. Room was comfortable. "
The price is P 8,789
per night
May 5 - May 6
Courtyard by Marriott Lenox Berkshires
Exterior
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1001)
"Set back from the road, clean and friendly staff"
The price is P 7,815
per night
May 11 - May 12
Hampton Inn & Suites Berkshires-Lenox
Terrace/patio
Hilton Garden Inn Lenox Pittsfield
3.0 star property
9.2 out of 10, Wonderful, (579)
"Very good"
The price is P 8,425
per night
May 11 - May 12
Hilton Garden Inn Lenox Pittsfield
Exterior
Club Wyndham Bentley Brook
3.0 star property
9.2 out of 10, Wonderful, (431)
"The staff was wonderful. The suite had everything that we needed and felt like home. I was there for a hiking trip and location was convenient and loved being able to relax in a jacuzzi afterwards. "
Club Wyndham Bentley Brook
Exterior
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1001)
"My overall experience at the Yankee was very good, my only complaint is the shower. The water took forever to warm up and when it eventually did it was moderately warm, never got hot, and the water pressure was poor. Otherwise my stay there was all I needed it to be"
The price is P 6,832
per night
May 8 - May 9
The Yankee, Trademark Collection by Wyndham
Exterior
Berkshire Valley Inn
2.5 star property
9.0 out of 10, Wonderful, (498)
"Berkshire valley inn is special for many reasons. They have reconfigured some of the classic hotel rooms into 3 or 4 bedroom suites with a kitchen. They have built a dog run on the hill behind the hotel. They serve delicious gluten free (!) muffins and frittata as well as gluten-full items. They have decorated in a cute and modern style that is unpretentious and comfortable. And the proprietor is lovely, she even called me when she found something we left behind. I hope to visit again in warmer...
The price is P 7,170
per night
May 5 - May 6
Berkshire Valley Inn
Interior
Cozy Corner Motel
2.0 star property
9.0 out of 10, Wonderful, (677)
"Nice, clean accommodation. Beds are comfortable. "
The price is P 4,340
per night
May 5 - May 6
Cozy Corner Motel
Fridge, microwave, stovetop, coffee/tea maker
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (308)
"Nice and clean, staff were excellent"
The price is P 8,617
per night
May 9 - May 10
Berkshire Mountain Lodge
Exterior
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (263)
"The rooms were nicely laid out and well designed. The property was very clean and quiet. It looked brand new."
The price is P 9,310
per night
May 6 - May 7
Fairfield Inn & Suites by Marriott Williamstown
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (103)
"It was clean and quiet good Breakfast "
The price is P 12,649
per night
May 5 - May 6
The Trail in Adams - Berkshires’ Art Hotel
Exterior
Willows Motel Williamstown
2.0 star property
8.8 out of 10, Excellent, (786)
"Super friendly staff—amazing family. A little dated, but very clean and comfortable."
The price is P 4,340
per night
May 16 - May 17
Willows Motel Williamstown
Exterior
The Villager Motel
2.0 star property
8.8 out of 10, Excellent, (592)
"I arrived well after midnight, but called ahead and my room was waiting for me. The room was clean and it was in a safe area. Definitely worth the money!"
The price is P 3,990
per night
May 5 - May 6
The Villager Motel
Courtyard
The Springs Motel
2.0 star property
8.8 out of 10, Excellent, (24)
"The Springs is a wonderful place! The renovations are so well done. We've stayed 3 times in 3 different rooms all were excellent but the honeymoon suite is my favorite. The beds are comfortable and the rooms are clean. The retro vibe of the place is downright adorable. With firepits, grills and a multitude of outdoor activities it was like staying at a mini resort. The staff is wonderful. The Springs is tucked away from the hustle and bustle of the area so it's quiet and safe but you will need...
The Springs Motel
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1672)
"Very nice spot quiet "
The price is P 9,749
per night
May 11 - May 12
Vacation Village in the Berkshires
Hypo-allergenic bedding, laptop workspace, blackout drapes
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (913)
"We enjoyed our stay and would definitely stay here again should we return to the area. Comfy beds, lots of pillows and simple white bedding. Loved the view of downtown from our windows. The artwork throughout was really a refreshingly unique way to decorate! Negatives we experienced - There was a barking dog a few doors down the hall but he stopped after approximately 30 minutes. Also when an adjacent room let their door swing shut, it caused our beds and headboards to bounce! Neither one of...
The price is P 8,616
per night
May 5 - May 6
Hotel Downstreet
Reception
Williamstown Motel
2.0 star property
8.6 out of 10, Excellent, (544)
"Very friendly "
The price is P 4,626
per night
May 8 - May 9
Williamstown Motel
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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.

More cheap stays in Cheshire

Quality Inn

Quality Inn

170 Housatonic Street, Lee, MA
The price is P5,148 per night from May 7 to May 8
P5,148
per night
7 May - 8 May
8/10 Very Good! (880 reviews)

Near an Attraction

Image for St Mary's of the Assumption Church

St Mary's of the Assumption Church

Learn about the local history of Cheshire with a stop at St Mary's of the Assumption Church. Discover the area's mountain views, or seek out its ski slopes.

See properties
St Mary's of the Assumption Church

Cheshire hotels information

Number of reviews
4,583
Accommodation
883 hotels
Lowest Price
P3,990
Highest Price
P16,080

Frequently asked questions

What's the best place to stay in Cheshire?

Located 13.4 mi (21.6 km) from the heart of Cheshire, Life House Berkshires is a top choice for your stay based on our traveler data. Other good options for your stay in the area are The Red Lion Inn and The Black Swan Lee - Lenox, Ascend Hotel Collection. 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 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. See all available hotels listed as LGBTQ-friendly in Cheshire.

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.

Book Cheshire hotels on Expedia USA

Recent Reviews in Cheshire
Expedia verified reviews

The Red Lion Inn

The Red Lion Inn

5/5 Excellent
"Quaint, quiet and peaceful."
A verified traveler stayed at The Red Lion Inn
Posted 19 hours ago
The Red Lion Inn