Photo by Ed Gaffny

Find hotels in Cheshire, MA from 1.873.129 ₫

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Top 10 Cheshire hotels and places to stay

Our top choices for Cheshire hotels

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (732)
"Great quiet stay. "
The price is 2.344.705 ₫
2.618.956 ₫ total
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel

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 2.581.810 ₫
2.883.882 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (111)
"Lovely Inn and very responsive and approachable staff. "
The price is 1.920.550 ₫
3.436.160 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Blooming Inn

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 6.910.294 ₫
7.304.181 ₫ total
includes taxes & fees
9 Sept - 10 Sept
Harbour House Inn

The Springs Motel

2.0 star property
9.2 out of 10, Wonderful, (62)
"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 2.999.378 ₫
3.290.319 ₫ total
includes taxes & fees
1 Sept - 2 Sept
The Springs Motel

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (942)
"Comfortable, clean, and great continental breakfast options! "
The price is 2.347.340 ₫
2.622.118 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Willows Motel Williamstown

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 2.081.255 ₫
2.324.683 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is 3.336.594 ₫
3.726.975 ₫ total
includes taxes & fees
7 Sept - 8 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is 4.004.440 ₫
4.472.959 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Element Lenox Berkshires

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (605)
"Very clean place for a very good price "
The price is 2.599.856 ₫
3.492.586 ₫ total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge

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 2.228.787 ₫
2.622.382 ₫ total
includes taxes & fees
3 Sept - 4 Sept
Cozy Corner Motel

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 3.363.730 ₫
4.787.244 ₫ total
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires

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 2.347.339 ₫
2.621.978 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Williamstown Motel

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 4.680.189 ₫
5.816.318 ₫ total
includes taxes & fees
29 Sept - 30 Sept
The Porches Inn at Mass MoCA

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1009)
"Good location, lovely grounds, we enjoyed the pool"
The price is 3.129.786 ₫
3.495.971 ₫ total
includes taxes & fees
1 Sept - 2 Sept
The Yankee, Trademark Collection by Wyndham

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (573)
"Excellent place. Bountiful view. "
The price is 3.293.125 ₫
3.678.552 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Maple Terrace Motel

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 2.798.893 ₫
3.126.363 ₫ total
includes taxes & fees
3 Sept - 4 Sept
Best Western Plus Berkshire Hills Inn & Suites

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1982)
"Beautiful location!"
The price is 2.853.665 ₫
3.476.548 ₫ total
includes taxes & fees
14 Sept - 15 Sept
Vacation Village in the Berkshires

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (702)
"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 4.232.087 ₫
4.727.241 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Berkshires Untold

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1010)
"Great location!"
The price is 3.961.498 ₫
4.424.992 ₫ 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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Accommodation near Cheshire attractions

St Mary's of the Assumption Church

St Mary's of the Assumption Church

St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views or seek out its ski slopes.

Learn more about Cheshire

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

Photo by Ed Gaffny
Open Photo by Ed Gaffny

Top Cheshire Hotel Reviews

More cheap stays in Cheshire

More cheap stays in Cheshire

Hotels in Cheshire with star rating

Hotels in Cheshire with star rating

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.