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Hotels in Cheshire

Photo by Ed Gaffny

Choose from 923 Cheshire Hotel Deals

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 $144 per night from Dec 24 to Dec 25
$144
includes taxes & fees
Dec 24 - Dec 25
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)
"Stayed for a weekend wedding and it was a great location. Room was large"

Reviewed on Dec 19, 2024

Hotel Downstreet
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 $108 per night from Jan 1 to Jan 2
$108
includes taxes & fees
Jan 1 - Jan 2, 2025
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! (1,001 reviews)
"This hotel was awesome! We enjoyed the hot tub along with the fireplace in our room!"

Reviewed on Dec 15, 2024

The Yankee, Trademark Collection by Wyndham
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 $99 per night from Jan 5 to Jan 6
$99
includes taxes & fees
Jan 5 - Jan 6, 2025
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! (455 reviews)
"The coziest best hotel in area! Staff was so wonderful, room was perfect! Lobby bar and lounge is so great."

Reviewed on Dec 19, 2024

Life House Berkshires
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 $144 per night from Jan 6 to Jan 7
$144
includes taxes & fees
Jan 6 - Jan 7, 2025
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! (1,000 reviews)
Heritage stay at an old Inn
"It is one of the oldest inns in America - so it creaks a lot, uneven floors, and for sure that look of old.. not necessarily bad... just a heritage property that has its quirks. We liked it.. the bed could be better for sure... I think that's the main fault.. the restaurant and pub were wonderful, ..."

Reviewed on Dec 16, 2024

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
The price is $113 per night from Dec 30 to Dec 31
$113
includes taxes & fees
Dec 30 - Dec 31
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 ...
8.8/10 Excellent! (1,000 reviews)
"Good"

Reviewed on Dec 9, 2024

The Black Swan Lee - Lenox, Ascend Hotel Collection
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 $111 per night from Jan 5 to Jan 6
$111
includes taxes & fees
Jan 5 - Jan 6, 2025
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! (701 reviews)
"Staff was very accommodating. The pool area was quite nice and it was deep"

Reviewed on Dec 16, 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
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 $158 per night from Jan 6 to Jan 7
$158
includes taxes & fees
Jan 6 - Jan 7, 2025
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 helpful staff in our ...
8.8/10 Excellent! (571 reviews)
"Westayed at the resort for the Stockbridge Christmas weekend location was so convenient to town, dining and events, Resort facilities were extra special pool movie theatre and resort Christmas themed activities would recommend."

Reviewed on Dec 9, 2024

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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 $210 per night from Jan 1 to Jan 2
$210
includes taxes & fees
Jan 1 - Jan 2, 2025
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! (389 reviews)
"It was a very positive experience. I would return."

Reviewed on Dec 16, 2024

The Williams Inn
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
The price is $216 per night from Jan 1 to Jan 2
$216
includes taxes & fees
Jan 1 - Jan 2, 2025
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, and in-room massages. Our guests praise the helpful staff in our ...
8.6/10 Excellent! (1,748 reviews)
"Nice and quiet family get a way"

Reviewed on Dec 16, 2024

Vacation Village in the Berkshires
The Constance, The Whitlock, & The Dewey By The Lenox Collection
The Constance, The Whitlock, & The Dewey 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
The price is $155 per night from Dec 30 to Dec 31
$155
includes taxes & fees
Dec 30 - Dec 31
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. ...
8.4/10 Very Good! (359 reviews)
"It was amazing! The staff was incredible, the room was very clean and cozy, and overall was a great place to stay. Loved it here!"

Reviewed on Dec 21, 2024

The Constance, The Whitlock, & The Dewey By The Lenox Collection
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 $94 per night from Jan 12 to Jan 13
$94
includes taxes & fees
Jan 12 - Jan 13, 2025
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! (1,000 reviews)
"Nice and clean rooms, great variety of free breakfast selections"

Reviewed on Dec 8, 2024

Quality Inn
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
3 out of 5
70 Pittsfield Rd, Lenox, MA
  • 31 min drive from St Mary's of the Assumption Church
The price is $155 per night from Jan 9 to Jan 10
$155
includes taxes & fees
Jan 9 - Jan 10, 2025
Stay at this 3-star business-friendly hotel in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (541 reviews)
"Staff were pleasant and helpful. Limited menu at the hotel's bistro, but two restaurants across the busy road. Pool is much smaller than it looks in the photo and hot tub was too hot. Rooms somewhat small but well laid-out."

Reviewed on Dec 2, 2024

Courtyard by Marriott Lenox Berkshires
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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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 923 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 $94. 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.

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Frequently Asked Questions About Cheshire hotels

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

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How many hotels are there in Cheshire?

With over 923 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 $94.

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.