Find Hotel Wedding Venues in Cheshire, MA

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Check availability on Cheshire Hotel Wedding Venues

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top Cheshire Hotel Wedding Venues

Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is SAR 767
SAR 810 total
includes taxes & fees
7 Jan - 8 January 2026
Harbour House Inn
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (982)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is SAR 345
SAR 385 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is SAR 528
SAR 758 total
includes taxes & fees
5 Jan - 6 January 2026
The Red Lion Inn
Front of property
UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center

2.0 star property
Rowe
The price is SAR 559
SAR 591 total
includes taxes & fees
8 Dec - 9 Dec
UU Rowe Camp and Conference Center
Front of property - evening/night
The Williams Inn

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (546)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is SAR 710
SAR 793 total
includes taxes & fees
8 Dec - 9 Dec
The Williams Inn
Room (King Room) | Iron/ironing board, free WiFi, bed sheets
Gateways Inn & Restaurant

Gateways Inn & Restaurant

3.0 star property
Lenox
8.0 out of 10, Very Good, (192)
"Very well kept property, nice restaurant and is in a great area"
United States
Josephine
The price is SAR 548
SAR 639 total
includes taxes & fees
6 Jan - 7 January 2026
Gateways Inn & Restaurant
Miscellaneous
1896 House Country Inn & Motels

1896 House Country Inn & Motels

2.5 star property
Williamstown
6.6 out of 10, (448)
"The price is good. It's a classic motel from the '50's, but gets the job done."
United States
edson
1896 House Country Inn & Motels
Business center
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is SAR 1,433
SAR 1,734 total
includes taxes & fees
28 Dec - 29 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm 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.
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Top Cheshire Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly. "
Brendan 1-night trip
Posted 3 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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