Find hotels in Cheshire, MA from 1.797.821 ₫
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18 Sep - 20 SepOur top choices for Cheshire hotels
1. Harbour House Inn
Harbour House InnCheshire
Gregory
6.575.397 ₫
6.950.195 ₫ total
includes taxes & fees
21 Sept - 22 Sept
2. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
Sarah
2.467.255 ₫
3.040.398 ₫ total
includes taxes & fees
15 Sept - 16 Sept
3. The Yankee Inn
The Yankee InnLenox
Karen
3.006.488 ₫
3.358.247 ₫ total
includes taxes & fees
22 Sept - 23 Sept
4. Maple Terrace Motel
Maple Terrace MotelWilliamstown
Christine
3.241.500 ₫
3.620.885 ₫ total
includes taxes & fees
14 Sept - 15 Sept
5. Cozy Corner Motel
Cozy Corner MotelWilliamstown
Janis
2.287.202 ₫
2.688.370 ₫ total
includes taxes & fees
13 Sept - 14 Sept
6. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
Robert
2.064.170 ₫
2.884.998 ₫ total
includes taxes & fees
1 Oct - 2 Oct
7. Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
Chris
2.683.809 ₫
2.997.676 ₫ total
includes taxes & fees
21 Sept - 22 Sept
8. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
BONNIE
3.723.121 ₫
4.158.726 ₫ total
includes taxes & fees
20 Sept - 21 Sept
9. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Joe
2.743.087 ₫
3.064.028 ₫ total
includes taxes & fees
13 Sept - 14 Sept
10. Hotel On North
Hotel On NorthPittsfield
Drew
3.479.492 ₫
3.886.593 ₫ total
includes taxes & fees
13 Sept - 14 Sept
11. Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham WilliamstownWilliamstown
Donna
2.850.721 ₫
3.184.286 ₫ total
includes taxes & fees
11 Oct - 12 Oct
12. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
Debra
2.980.570 ₫
3.329.297 ₫ total
includes taxes & fees
12 Oct - 13 Oct
13. The Williams Inn
The Williams InnWilliamstown
John
5.037.291 ₫
5.626.655 ₫ total
includes taxes & fees
13 Sept - 14 Sept
14. Williamstown Motel
Williamstown MotelWilliamstown
Ahmet
2.567.268 ₫
2.867.638 ₫ total
includes taxes & fees
13 Sept - 14 Sept
15. The Villager Motel
The Villager MotelWilliamstown
Rebecca
2.307.948 ₫
2.577.900 ₫ total
includes taxes & fees
13 Sept - 14 Sept
16. The Springs Motel
The Springs MotelNew Ashford
Elizabeth
2.944.933 ₫
3.230.592 ₫ total
includes taxes & fees
13 Sept - 14 Sept
17. Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott WilliamstownWilliamstown
C. David
4.655.313 ₫
5.199.985 ₫ total
includes taxes & fees
15 Sept - 16 Sept
18. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox BerkshiresLenox
Tracy
5.179.917 ₫
5.785.968 ₫ total
includes taxes & fees
1 Oct - 2 Oct
19. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
Nancy
3.551.128 ₫
3.966.609 ₫ total
includes taxes & fees
30 Sept - 1 Oct
20. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
Steve
3.282.515 ₫
3.666.569 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Stay near popular Cheshire attractions
St Mary's of the Assumption Church
10.0/10 (1 review)
This historic Catholic parish has served Cheshire's community since 1879, offering a serene space for reflection. Visit during religious holidays to experience special services in its traditional architectural setting.
Learn more about Cheshire
Get away to romantic Cheshire! Enjoy the skiing, hiking and natural setting.
See all hotels in Cheshire
Top Cheshire Hotel Reviews
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"Great location for Mass Moca"
Vacation Village in the Berkshires
10/10 Excellent
"Beautiful location and views. Spacious room with all amenities."
Berkshire Mountain Lodge
8/10 Good
"Loved having a full Kitchen, lots of space"
Berkshires Untold
10/10 Excellent
"beautiful place, great staff, would love to go back!"
The Yankee Inn
10/10 Excellent
"Excellent in every way. Service, staff, amenities. Everything was perfect."
Willows Motel Williamstown
10/10 Excellent
"Awesome staff plus pet-friendly."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"Generous front desk (forgot toothbrush & comb, they gave us both free of charge). Great complimentary breakfast & tea/coffee machine. Great WiFi. Beautiful view & kayaking was so fun. We had a wonderful stay!"
Holiday Inn Club Vacations Oak 'n Spruce Resort
8/10 Good
"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."
Jiminy Peak Mountain Resort
10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
More cheap stays in Cheshire
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
1.609.508 ₫
1.797.821 ₫ total
14 Sept - 15 Sept
includes taxes & fees
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
2.743.087 ₫
3.064.028 ₫ total
13 Sept - 14 Sept
includes taxes & fees
8.4/10 Very good! (1,017 reviews)
Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
2.777.317 ₫
3.102.264 ₫ total
24 Sept - 25 Sept
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
The Yankee Inn
461 Pittsfield Rd Lenox MA
3.006.488 ₫
3.358.247 ₫ total
22 Sept - 23 Sept
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
3.282.515 ₫
3.666.569 ₫ total
13 Sept - 14 Sept
includes taxes & fees
The Whitlock
16 Church St Lenox MA
3.723.121 ₫
4.158.727 ₫ total
13 Sept - 14 Sept
includes taxes & fees
8.4/10 Very good! (378 reviews)
Hotels in Cheshire with star rating
4 Star Hotels
10 properties
3 Star Hotels
108 properties
2 Star Hotels
49 properties
