Photo by Ed Gaffny

Find hotels in Cheshire, MA from 1.668.975 ₫

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Check prices for these dates

Tonight
5 Jul - 6 Jul
Tomorrow
6 Jul - 7 Jul
Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul

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Top 10 Cheshire hotels and places to stay

Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (50)
"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 6.867.014 ₫
7.258.434 ₫ total
includes taxes & fees
7 Jul - 8 Jul
Harbour House Inn
Cozy Corner Motel
Gazebo

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (829)
"Very, very clean with friendly owners. Located within a few minutes' drive of good restaurants and outdoor recreation areas. We would definitely stay again!"
The price is 2.487.100 ₫
2.918.285 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Cozy Corner Motel
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (549)
"Very clean and very nice staff. Breakfast was great"
The price is 4.116.805 ₫
4.598.517 ₫ total
includes taxes & fees
31 Jul - 1 Aug
Berkshire Valley Inn
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1003)
"Fantastic place"
The price is 3.760.757 ₫
4.200.765 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Hotel Downstreet, Ascend Hotel Collection
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Everyone was very nice to us! "
The price is 5.318.467 ₫
5.940.727 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Hampton Inn & Suites Berkshires-Lenox
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is 4.948.020 ₫
5.526.860 ₫ total
includes taxes & fees
21 Jul - 22 Jul
Hotel On North
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (394)
"Perfect for our needs"
The price is 5.540.997 ₫
6.774.155 ₫ total
includes taxes & fees
4 Aug - 5 Aug
The Porches Inn at Mass MoCA
The Williams Inn
Front of property – evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (459)
"Wonderful stay. Helpful, professional staff. "
The price is 6.471.696 ₫
7.228.884 ₫ total
includes taxes & fees
9 Jul - 10 Jul
The Williams Inn
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (101)
"Great Place to stay in Small town"
The price is 2.309.076 ₫
3.600.258 ₫ total
includes taxes & fees
9 Jul - 10 Jul
Blooming Inn
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow
Williamstown Motel
Reception

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (271)
"a perfecf place to stay as we enjoyed the weekend of fun in the berkshires! the owner was extemely friendly, the room was very clean and comfortable and the location is well located. we would definitely return! "
The price is 2.330.020 ₫
2.602.632 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Williamstown Motel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (665)
"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"
The price is 4.037.585 ₫
4.875.455 ₫ total
includes taxes & fees
9 Jul - 10 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (943)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
The price is 4.686.220 ₫
5.234.509 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Jiminy Peak Mountain Resort
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1003)
"Friendly staff, easy parking"
The price is 3.093.167 ₫
3.455.068 ₫ total
includes taxes & fees
21 Jul - 22 Jul
Quality Inn
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"I had excellent stay at the Red Lion Inn "
The price is 5.733.420 ₫
7.573.874 ₫ total
includes taxes & fees
4 Aug - 5 Aug
The Red Lion Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (367)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1850)
"Clean easy to get to and everything we needed"
Vacation Village in the Berkshires
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (559)
"The hotel is very clean, well-managed, and quiet, and it's conveniently located near Tanglewood and other attractions. The room is clean, and the staff are all extremely kind and attentive to our needs (special thanks to Tapan!) We will definitely be coming back!"
The price is 5.550.160 ₫
6.199.529 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Courtyard by Marriott Lenox Berkshires
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (414)
"Very cute and clean room. After driving all day we were so happy to see all muffins, scones, yogurt, cereal, oatmeal, strawberries, milk, OJ, hot chocolate and coffee already in the room for breakfast the next day. We had a great stay, thank you!"
The price is 5.105.100 ₫
5.600.294 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Shaker Mill Inn
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (502)
"We enjoyed our stay here. It was very quiet, and had everything we needed."
Berkshire Mountain Lodge
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 wildlife.

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

Frequently asked questions

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.