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Hotels in Cheshire

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Choose from 953 Cheshire Hotel Deals

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 $108 per night from Apr 14 to Apr 15
$108
includes taxes & fees
Apr 14 - Apr 15
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! (537 reviews)
"Excellent stay at this beautiful property!"

Reviewed on Mar 25, 2025

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 $99 per night from Apr 7 to Apr 8
$99
includes taxes & fees
Apr 7 - Apr 8
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! (1,002 reviews)
"We highly recommend it!! My husband go there often for work and we usually stayed there. Very nice place!!"

Reviewed on Mar 28, 2025

The Yankee, Trademark Collection by Wyndham
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 $158 per night from Apr 20 to Apr 21
$158
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,791 reviews)
"The location to jimney peak was great."

Reviewed on Mar 26, 2025

Vacation Village in the Berkshires
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
The price is $147 per night from Apr 1 to Apr 2
$147
includes taxes & fees
Apr 1 - Apr 2
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! (613 reviews)
"Clean and great location"

Reviewed on Mar 28, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 $249 per night from Apr 1 to Apr 2
$249
includes taxes & fees
Apr 1 - Apr 2
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! (431 reviews)
"Staff was excellent - duper friendly and helpful. The Inn is pretty and room comfortable."

Reviewed on Mar 29, 2025

The Williams Inn
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
The price is $141 per night from Apr 13 to Apr 14
$141
includes taxes & fees
Apr 13 - Apr 14
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)
"The hotel services were really nice and the rooms were spacious."

Reviewed on Mar 25, 2025

Hotel Downstreet, 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 $178 per night from Apr 15 to Apr 16
$178
includes taxes & fees
Apr 15 - Apr 16
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! (1,002 reviews)
"Great place if you’re a history buff"

Reviewed on Mar 27, 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
The price is $103 per night from Apr 6 to Apr 7
$103
includes taxes & fees
Apr 6 - Apr 7
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! (1,000 reviews)
"Beautiful views of the lake with cozy rooms. Staff is excellent."

Reviewed on Mar 20, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
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 $100 per night from May 1 to May 2
$100
includes taxes & fees
May 1 - May 2
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! (381 reviews)
"This inn is located in a very convenient location to the town center where there are numerous boutique shops. The inn itself is quiet, clean, and safe, with a small 24-hour open dining room with a coffee station that offers Green Mountain coffee pods, and pop-corn and cracker snacks. The stay includes ..."

Reviewed on Mar 25, 2025

The Constance, The Whitlock, & The Dewey By The Lenox Collection
Hotel On North
Hotel On North
3.5 out of 5
297 North Street, Pittsfield, MA
  • 18 min drive from St Mary's of the Assumption Church
The price is $122 per night from Apr 1 to Apr 2
$122
includes taxes & fees
Apr 1 - Apr 2
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (697 reviews)
"Staff was very helpful and kind"

Reviewed on Mar 28, 2025

Hotel On North
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 $144 per night from Apr 27 to Apr 28
$144
includes taxes & fees
Apr 27 - Apr 28
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! (443 reviews)
Great family time
"We had a great time at the hotel. My sons and I loved spending time in the pool and the hot tub. The bedroom was spacious, the kitchen had everything we needed, and the bathroom was ample and clean."

Reviewed on Mar 16, 2025

Berkshire Mountain Lodge
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
The price is $116 per night from Apr 12 to Apr 13
$116
includes taxes & fees
Apr 12 - Apr 13
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! (763 reviews)
"Easy check in, nice staff. Rug in the room was kind of musty. They were accommodating to me requesting to have a slightly later check out. Would return if in the area."

Reviewed on Mar 18, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 953 properties in Cheshire
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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Frequently Asked Questions About Cheshire hotels

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How many hotels are there in Cheshire?

With over 953 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 $99.

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.