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Hotels in Cheshire

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Choose from 987 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 ...
Vacation Village in the Berkshires
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 ...
Hotel Downstreet, 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 business center. Our guests praise the helpful staff and the clean rooms in ...
Berkshire Mountain Lodge
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 ...
Berkshires Untold
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 ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
  • 16 min drive from St Mary's of the Assumption Church
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
FairBridge Inn Express
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 ...
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
  • 27 min drive from St Mary's of the Assumption Church
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Howard Johnson by Wyndham Lenox
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 ...
The Williams Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
  • 27 min walk from St Mary's of the Assumption Church
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ...
Jiminy Peak Mountain Resort
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 ...
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
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 ...
The Black Swan Lee - Lenox, Ascend Hotel Collection
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

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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 987 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 $88. 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 $88.

How many hotels are there in Cheshire?

With over 987 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 $88.

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.