Photo by Ed Gaffny

Cheshire Hotels

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29 Aug - 30 Aug
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30 Aug - 31 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sept - 7 Sept

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Top 10 trending Cheshire hotels

Our top choices for Cheshire hotels

Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (942)
"Comfortable, clean, and great continental breakfast options! "
The price is €85
includes taxes & fees
2 Sept - 3 Sept
Willows Motel Williamstown
Gregory House Country Inn
Front of property

Gregory House Country Inn

3.0 star property
8.8 out of 10, Excellent, (57)
"Big rooms, very friendly staff and great pizza!"
The price is €107
includes taxes & fees
31 Aug - 1 Sept
Gregory House Country Inn
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (732)
"Great quiet stay. "
The price is €85
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel
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 €238
includes taxes & fees
9 Sept - 10 Sept
Harbour House Inn
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 €112
includes taxes & fees
9 Sept - 10 Sept
Blooming Inn
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Great staff! Comfortable bed! "
The price is €137
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn & Suites Berkshires-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, (1004)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is €121
includes taxes & fees
11 Sept - 12 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (850)
"We thoroughly enjoyed our 1-night stay at the Cozy Corner! Rooms were very clean, and beds very comfortable! They also had a great breakfast, and I loved the outdoor seating area by the babbling brook!"
The price is €85
includes taxes & fees
3 Sept - 4 Sept
Cozy Corner Motel
Tanglewood Suites
2 Bedrooms 1 Bath

Tanglewood Suites

2.5 star property
7.2 out of 10, Good, (19)
"The owner did not honor our confirmed Expedia reservation, so we had to find a hotel at the last minute. She made up various excuses and was very rude."
The price is €230
includes taxes & fees
30 Aug - 31 Aug
Tanglewood Suites
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 €85
includes taxes & fees
7 Sept - 8 Sept
Williamstown Motel
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (787)
"My stay was perfect. I can't wait to stay there again. "
The price is €76
includes taxes & fees
11 Sept - 12 Sept
Howard Johnson by Wyndham Lenox
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, (1002)
"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 €156
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (572)
"Excellent place. Bountiful view. "
The price is €120
includes taxes & fees
2 Sept - 3 Sept
Maple Terrace Motel
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1007)
"Wonderful place to stay"
The price is €120
includes taxes & fees
21 Sept - 22 Sept
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, (760)
"Quite and good location to around towns"
The price is €152
includes taxes & fees
28 Sept - 29 Sept
Hotel On North
The Porches Inn at Mass MoCA
Suite, 2 Bedrooms

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (413)
"Great well managed property with a unique style and nice amenities. Also, a continental breakfast is included with the stay."
The price is €189
includes taxes & fees
28 Sept - 29 Sept
The Porches Inn at Mass MoCA
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (482)
"Nice quaint out of the ordinary vacation experience. "
The price is €166
includes taxes & fees
1 Sept - 2 Sept
Whistler's Inn Bed & Breakfast
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (422)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is €154
includes taxes & fees
4 Sept - 5 Sept
Shaker Mill Inn
Blue Vista Motor Lodge
Single Room

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (180)
"Clean, beautiful view wonderful service"
The price is €197
includes taxes & fees
1 Sept - 2 Sept
Blue Vista Motor Lodge
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, (1004)
"Very clean rooms and excellent staff."
The price is €102
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites
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 €76 per night from 11 Sept to 12 Sept
€76
11 Sept - 12 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.

What are some of the best holiday rentals that Cheshire has to offer?

Peace and quiet on the lake: This holiday home rental outside of Cheshire is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games 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 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.