Search for Cheap Deals on
Hotels in Cheshire

Photo by Ed Gaffny

Choose from 984 Cheshire Hotel Deals

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 27 min walk from St Mary's of the Assumption Church
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,818 reviews)
Pleasant and good value
"Pleasant stay in clean condition but slightly getting outdated."

Reviewed on Jun 7, 2025

Vacation Village in the 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
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! (1,005 reviews)
"Long weekend motorcycle trip. This hotel was very clean, an excellent location, friendly staff, very comfortable beds. We were not aware the property was undergoing renovation."

Reviewed on Jun 9, 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
  • 48 min drive from St Mary's of the Assumption Church
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (650 reviews)
"Great place for a family."

Reviewed on Jun 9, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,002 reviews)
"I liked this place. Staff couldn't be nicer and pretty good free breakfast. Please loves dogs too and some nice grassy areas in the back to walk them."

Reviewed on Jun 6, 2025

Best Western Plus Berkshire Hills Inn & Suites
Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
3 out of 5
40 Main St, North Adams, MA
  • 23 min drive from St Mary's of the Assumption Church
Stay at this 3-star 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 ...
8.6/10 Excellent! (1,000 reviews)
Ideal spot in town
"Great central location, clean, quiet."

Reviewed on May 24, 2025

Hotel Downstreet, Ascend Hotel Collection
Berkshires Untold
Berkshires Untold
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
  • 29 min drive from St Mary's of the Assumption Church
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! (602 reviews)
"Gorgeous decor, unique ambiance, excellent food and drinks.... I can't wait to return"

Reviewed on Jun 6, 2025

Berkshires Untold
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3 out of 5
One West Street, Pittsfield, MA
  • 19 min drive from St Mary's of the Assumption Church
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (791 reviews)
"I thoroughly enjoyed my stay. The room was very clean, the pillows were so thick and fluffy and the furniture pieces in the room were tasteful and comfortable"

Reviewed on Jun 6, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Constance by the Lenox Collection
The Constance by 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
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (413 reviews)
"Quaint, comfortable but limited amenities."

Reviewed on Jun 8, 2025

The Constance by the Lenox 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
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,001 reviews)
"Quintessential Berkshire Inn."

Reviewed on Jun 1, 2025

The Red Lion Inn
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
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,006 reviews)
"Very good service and breakfast!"

Reviewed on Jun 4, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
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
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (488 reviews)
"Beautiful"

Reviewed on Jun 8, 2025

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
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (455 reviews)
"Never gave us our welcome gift."

Reviewed on May 29, 2025

The Williams Inn
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.

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 984 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 . 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 great 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 unlock great deals on 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 .

How many hotels are there in Cheshire?

With over 984 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 .

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 unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.