Photo by Ed Gaffny

Find hotels in Cheshire, MA from ฿2,183

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Top 10 Cheshire hotels and places to stay

The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (732)
"Great quiet stay. "
The price is ฿2,878
฿3,214 total
includes taxes & fees
2 Sept - 3 Sept
The Villager Motel
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is ฿3,169
฿3,540 total
includes taxes & fees
2 Sept - 3 Sept
Huttopia Berkshires
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (111)
"Lovely Inn and very responsive and approachable staff. "
The price is ฿2,183
฿4,022 total
includes taxes & fees
3 Sept - 4 Sept
Blooming Inn
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"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!! "
The price is ฿8,481
฿8,965 total
includes taxes & fees
9 Sept - 10 Sept
Harbour House Inn
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
9.2 out of 10, Wonderful, (63)
"I was pleasantly surprised to find this gem in the middle of town. Relatively inexpensive for the area. Clean rooms and property. Nice staff. Beautiful pool. Would definitely recommend "
The price is ฿3,681
฿4,038 total
includes taxes & fees
2 Sept - 3 Sept
The Springs Motel
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (943)
"Comfortable, clean, and great continental breakfast options! "
The price is ฿2,881
฿3,218 total
includes taxes & fees
2 Sept - 3 Sept
Willows Motel Williamstown
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (790)
"My stay was perfect. I can't wait to stay there again. "
The price is ฿2,554
฿2,853 total
includes taxes & fees
2 Sept - 3 Sept
Howard Johnson by Wyndham Lenox
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ฿4,095
฿4,574 total
includes taxes & fees
7 Sept - 8 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Element Lenox Berkshires
Exterior

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is ฿5,465
฿6,104 total
includes taxes & fees
8 Sept - 9 Sept
Element Lenox Berkshires
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (609)
"Very clean place for a very good price "
The price is ฿3,191
฿4,287 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (851)
"We really enjoyed our time at Cozy Corner Motel. 100% recommended "
The price is ฿2,736
฿3,219 total
includes taxes & fees
3 Sept - 4 Sept
Cozy Corner Motel
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1003)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is ฿4,129
฿5,876 total
includes taxes & fees
2 Sept - 3 Sept
The Cornell Inn, Lenox & The Berkshires
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (290)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is ฿2,881
฿3,218 total
includes taxes & fees
7 Sept - 8 Sept
Williamstown Motel
The Porches Inn at Mass MoCA
Suite, 2 Bedrooms | 2 bedrooms, Frette Italian sheets, premium bedding, down duvets

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (414)
"Great well managed property with a unique style and nice amenities. Also, a continental breakfast is included with the stay."
The price is ฿6,082
฿7,516 total
includes taxes & fees
8 Sept - 9 Sept
The Porches Inn at Mass MoCA
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1010)
"Good location, lovely grounds, we enjoyed the pool"
The price is ฿4,045
฿4,518 total
includes taxes & fees
21 Sept - 22 Sept
The Yankee, Trademark Collection by Wyndham
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (573)
"Excellent place. Bountiful view. "
The price is ฿4,042
฿4,515 total
includes taxes & fees
7 Sept - 8 Sept
Maple Terrace Motel
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, (1005)
"Very clean rooms and excellent staff."
The price is ฿3,435
฿3,837 total
includes taxes & fees
3 Sept - 4 Sept
Best Western Plus Berkshire Hills Inn & Suites
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1983)
"Beautiful location!"
The price is ฿3,503
฿4,267 total
includes taxes & fees
14 Sept - 15 Sept
Vacation Village in the Berkshires
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (705)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is ฿5,194
฿5,802 total
includes taxes & fees
2 Sept - 3 Sept
Berkshires Untold
Hotel Downstreet, an Ascend Collection Hotel
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1011)
"Great location!"
The price is ฿4,862
฿5,431 total
includes taxes & fees
1 Oct - 2 Oct
Hotel Downstreet, an Ascend Collection Hotel
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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Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking and lake views.

See all hotels in Cheshire
Photo by Ed Gaffny
Open Photo by Ed Gaffny

Top Cheshire Hotel Reviews

More cheap stays in Cheshire

More cheap stays in Cheshire

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is ฿2,554 per night from 2 Sept to 3 Sept
฿2,554
฿2,853 total
2 Sept - 3 Sept
includes taxes & fees

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's the best place to stay in Cheshire?

Harbour House Inn is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other choices for your trip to the area are Vacation Village in the Berkshires 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 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 4 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 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.