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Hotels in Cheshire

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Last Minute Hot Rate® Hotel Deals in Cheshire

We Hide Hotel Names So You Can Find 4-Star Hotels At 2-Star Prices. Choose the Location, Star Rating & Amenities. Let Hotwire Find You the Best Deal. Book Today!

Choose from 873 Cheshire Hotel Deals

The Lenox Collection
The Lenox Collection
3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
  • 34 min drive from St Mary's of the Assumption Church
The price is $125 per night from Jul 9 to Jul 10
$125
per night
Jul 9 - Jul 10
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (170 reviews)
"The propery is gorgeous. So charming. Staff was very friendly. Very nice room with awesome shower, super comfy bed, and quietly efficient air conditioner."

Reviewed on Jun 21, 2024

The Lenox Collection
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
  • 23 min drive from St Mary's of the Assumption Church
The price is $169 per night from Jul 1 to Jul 2
$169
per night
Jul 1 - Jul 2
Stay at this hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our ...
8.4/10 Very Good! (931 reviews)
Nifty hotel in a great little town
"The room was clean and distinctive. Everything worked properly. The hotel is perfectly located for accessing anything in town by foot, including MassMOCA and various eateries."

Reviewed on Jun 16, 2024

Hotel Downstreet
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
  • 29 min drive from St Mary's of the Assumption Church
The price is $150 per night from Jul 9 to Jul 10
$150
per night
Jul 9 - Jul 10
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (272 reviews)
"Very pleasant place to stay rooms and nice and clean. Staff is very nice."

Reviewed on Jun 21, 2024

Life House Berkshires
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
  • 27 min drive from St Mary's of the Assumption Church
The price is $144 per night from Jul 10 to Jul 11
$144
per night
Jul 10 - Jul 11
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,003 reviews)
"Employees were all super friendly, a very clean and pleasant property. There was nothing that I didn’t like about this place"

Reviewed on Jun 22, 2024

The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
  • 40 min drive from St Mary's of the Assumption Church
The price is $199 per night from Jun 27 to Jun 28
$199
per night
Jun 27 - Jun 28
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
8.8/10 Excellent! (1,008 reviews)
"The hotel was great! The rooms were clean and well appointed."

Reviewed on Jun 21, 2024

The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
  • 47 min drive from St Mary's of the Assumption Church
The price is $180 per night from Jul 22 to Jul 23
$180
per night
Jul 22 - Jul 23
Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the pool and the restaurant in our ...
8.8/10 Excellent! (905 reviews)
"Classic hotel but our room was far from main desk and fairly inconvenient. Room was in a separate annex"

Reviewed on Jun 23, 2024

The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 out of 5
190 Meadow Street, South Lee, MA
  • 48 min drive from St Mary's of the Assumption Church
The price is $179 per night from Jun 27 to Jun 28
$179
per night
Jun 27 - Jun 28
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the clean ...
8.8/10 Excellent! (490 reviews)
Family get away!
"Everything is excellent just right! Went in a short trip with the grandchildren and everyone loves the accommodations! Lot's to do for all ages!"

Reviewed on Jun 25, 2024

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Quality Inn
Quality Inn
2.5 out of 5
170 Housatonic Street, Lee, MA
  • 44 min drive from St Mary's of the Assumption Church
The price is $127 per night from Jul 9 to Jul 10
$127
per night
Jul 9 - Jul 10
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
8/10 Very Good! (926 reviews)
"Staff was courteous"

Reviewed on Jun 24, 2024

Quality Inn
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
  • 19 min drive from St Mary's of the Assumption Church
The price is $145 per night from Jul 10 to Jul 11
$145
per night
Jul 10 - Jul 11
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (592 reviews)
"under construction not great parking but finer undeer circuimdstances"

Reviewed on Jun 17, 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
  • 25 min drive from St Mary's of the Assumption Church
The price is $185 per night from Jun 27 to Jun 28
$185
per night
Jun 27 - Jun 28
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the clean rooms in our reviews. Popular ...
8.8/10 Excellent! (317 reviews)
"We have stayed in many hotels/Inns/Lodges in the past. My 5 year old daughter said, "this one is the best in which we have ever stayed." Looking forward to another stay in 6 days. Absolutely loved it."

Reviewed on Jun 3, 2024

Berkshire Mountain Lodge
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
  • 25 min drive from St Mary's of the Assumption Church
The price is $269 per night from Jun 27 to Jun 28
$269
per night
Jun 27 - Jun 28
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the clean rooms in our reviews. ...
9.6/10 Exceptional! (306 reviews)
"Great"

Reviewed on Jun 23, 2024

The Williams Inn
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
  • 22 min drive from St Mary's of the Assumption Church
The price is $143 per night from Jul 21 to Jul 22
$143
per night
Jul 21 - Jul 22
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (956 reviews)
"Excellent service"

Reviewed on Jun 2, 2024

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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

Find cheap hotels in Cheshire

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Cheshire hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Cheshire.

Choosing the right hotel in Massachusetts has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Cheshire’s 873 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $74. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get up to 60% Cheshire hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Cheshire. No matter your reason for visiting Cheshire, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Cheshire hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can save up to 60% off your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Cheshire for as low as $74.

How many hotels are there in Cheshire?

With over 873 hotels in Cheshire, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $74.

How to find cheap car rentals in Cheshire?

Finding a cheap car rental deal in Cheshire is as easy as scoring cheap hotels in Cheshire. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Cheshire now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Cheshire right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.