Photo by Ed Gaffny

Find hotels in Cheshire, MA from SAR 267

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Compare 987 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (732)
"Great quiet stay. "
The price is SAR 334
SAR 373 total
includes taxes & fees
1 Sep - 2 Sep
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 SAR 368
SAR 411 total
includes taxes & fees
1 Sep - 2 Sep
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 SAR 274
SAR 489 total
includes taxes & fees
3 Sep - 4 Sep
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 SAR 886
SAR 936 total
includes taxes & fees
9 Sep - 10 Sep
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 SAR 423
SAR 464 total
includes taxes & fees
1 Sep - 2 Sep
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 SAR 334
SAR 373 total
includes taxes & fees
1 Sep - 2 Sep
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 SAR 296
SAR 331 total
includes taxes & fees
1 Sep - 2 Sep
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 SAR 475
SAR 531 total
includes taxes & fees
7 Sep - 8 Sep
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 SAR 570
SAR 637 total
includes taxes & fees
7 Sep - 8 Sep
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 SAR 370
SAR 497 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 SAR 317
SAR 374 total
includes taxes & fees
3 Sep - 4 Sep
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 SAR 479
SAR 682 total
includes taxes & fees
1 Sep - 2 Sep
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 SAR 324
SAR 362 total
includes taxes & fees
14 Sep - 15 Sep
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 SAR 706
SAR 872 total
includes taxes & fees
8 Sep - 9 Sep
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 SAR 446
SAR 498 total
includes taxes & fees
1 Sep - 2 Sep
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 SAR 469
SAR 524 total
includes taxes & fees
2 Sep - 3 Sep
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 SAR 399
SAR 445 total
includes taxes & fees
2 Sep - 3 Sep
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 SAR 406
SAR 495 total
includes taxes & fees
14 Sep - 15 Sep
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 SAR 603
SAR 673 total
includes taxes & fees
1 Sep - 2 Sep
Berkshires Untold

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1010)
"Great location!"
The price is SAR 564
SAR 630 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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Stay near popular 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.

The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..
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 best place to stay in Cheshire?

Harbour House Inn is one of the top choices for your stay based on our traveler data. This B&B offers free breakfast and free parking. Other good options for your stay in 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 vacation rentals in Cheshire?

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

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 4 hotels and other accommodations to choose from. Find out more about Cheshire.

What are the top places to visit in Cheshire?

A favorite place to visit is Mount Greylock State Reservation. 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.