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Cheshire (MA) hotels and places to stay

Search among 74 available hotels and places to stay in Cheshire from 50+ providers.

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29Jan2023Sunday
30Jan2023Monday
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  • The bed & breakfast has
    • Flat-screen TV
  • The bed & breakfast has
    • Ski storage
  • The bed & breakfast has
    • Hiking
    • Fishing
    • Skiing
View on map1.2 mi from City Center50 yd from City Center
Situated 5 minutes' walk from Cheshire's downtown and less than 25 minutes on foot from First Baptist Church, this hotel offers a sundeck and a library.
7.6
Very good4 reviews
From   US$ 291 /nightSelect
Not available
Similar properties near Cheshire
  • The hotel has
    • Free Wi-Fi in rooms
  • The hotel has
    • On-site car park
  • The hotel has
    • 24-hour reception
    • 24-hour security
View on map10.4 mi from Cheshire10.4 mi from City Center
Situated in the heart of Williamstown and approximately 10 minutes' ride from Pine Cobble Mountain, the hotel offers 64 rooms.
8.4
Great2 reviews
From   US$ 208 /nightSelect
Not available
View on map8.9 mi from Cheshire8.9 mi from City Center
Overlooking the mountain, The hotel is located in an ski area of Pittsfield and in 5 minutes' walk from Museum Facsimiles Outlet Store.
8.0
Great6 reviews
From   US$ 143 /nightSelect
Not available
View on map10.0 mi from Cheshire10.0 mi from City Center
Offering unique rooms along with a hot tub and an outdoor swimming pool, the hotel lies 5 minutes' stroll of MASS MoCA and 10 minutes on foot from MCLA'S Gallery 51.
8.2
Great16 reviews
From   US$ 199 /nightSelect
Not available
Hotel
View on map9.6 mi from Cheshire9.6 mi from City Center
From   US$ 184 /nightSelect
Not available
Hotel
View on map12.2 mi from Cheshire12.2 mi from City Center
Overlooking mountain, this perfect hotel welcomes guests with a daily buffet breakfast.
8.4
Great75 reviews
From   US$ 83 /nightSelect
Not available
View on map11.7 mi from Cheshire11.7 mi from City Center
Situated less than 15 minutes' drive from Kirvin Park, this inn features a heated swimming pool, barbecue and entertainment activities.
From   US$ 162 /nightSelect
Not available
View on map9.2 mi from Cheshire9.2 mi from City Center
Offering access to an indoor swimming pool, this hotel also provides a sun deck, an indoor pool and a tennis court in near a train station and 5 minutes' stroll to Berkshire Museum.
7.4
Very good43 reviews
From   US$ 99 /nightSelect
Not available
View on map16.4 mi from Cheshire16.4 mi from City Center
While staying in the hotel you are invited to discover Mass Audubon's Pleasant Valley Wildlife Sanctuary, set 10 minutes by car, or Frelinghuysen Morris House and Studio, which is 2 miles away.
7.2
Very good5 reviews
From   US$ 119 /nightSelect
Not available
View on map10.0 mi from Cheshire10.0 mi from City Center
Located 4 miles from Hoosac Tunnel Museum, this hotel features an outdoor swimming pool along with sauna facilities and an outdoor swimming pool.
8.4
Great19 reviews
From   US$ 139 /nightSelect
Not available
View on map11.9 mi from Cheshire11.9 mi from City Center
While staying in the hotel you are invited to discover Hancock Shaker Village, set 4 miles away, or Bousquet Ski Area, which is around 20 minutes' stroll away.
7.6
Very good2 reviews
From   US$ 136 /nightSelect
Not available
View on map10.1 mi from Cheshire10.1 mi from City Center
Set about 15 minutes' walk from Williams College Museum of Art, this venue in Williamstown features a seasonal outdoor pool and a daily continental breakfast.
8.4
Great44 reviews
From   US$ 79 /nightSelect
Not available
View on map10.2 mi from Cheshire10.2 mi from City Center
While staying in the hotel you are invited to discover The Clark Art Institute, set a 10-minute drive away, or Massachusetts Museum of Contemporary Art, which is 4 miles away.
8.0
Great37 reviews
From   US$ 89 /nightSelect
Not available
View on map10.8 mi from Cheshire10.8 mi from City Center
There are rooms facing mountain and the hotel is set a 8-minute walk from Williams College.
7.4
Very good91 reviews
From   US$ 61 /nightSelect
Not available
View on map9.6 mi from Cheshire9.6 mi from City Center
Located 2 miles from Bousquet Ski Area, this inn features a seasonal outdoor swimming pool.
7.0
Very good51 reviews
From   US$ 80 /nightSelect
Not available
View on map12.2 mi from Cheshire12.2 mi from City Center
In 25 minutes' stroll of Arrowhead, this hotel features a seasonal outdoor swimming pool, a golf course and entertainment activities.
7.6
Very good68 reviews
From   US$ 69 /nightSelect
Not available
View on map12.3 mi from Cheshire12.3 mi from City Center
This comfortable 79-room hotel is located 25 minutes' stroll of Bousquet Ski Area and offers fitness classes, a gym and an indoor swimming pool along with toys and board games for guests with families.
9.0
Perfect29 reviews
From   US$ 110 /nightSelect
Not available
View on map12.1 mi from Cheshire12.1 mi from City Center
7.0
Very good34 reviews
From   US$ 59 /nightSelect
Not available
View on map10.8 mi from Cheshire10.8 mi from City Center
Offering a swimming pool, this hotel is just a 5-minute walk from Taconic Trail State Park.
7.8
Very good92 reviews
From   US$ 182 /nightSelect
Not available
View on map9.8 mi from Cheshire9.8 mi from City Center
Located 10 minutes' walk from North Adams city center, this hotel offers 90 rooms, a hot tub, sauna facilities and an indoor pool.
7.4
Very good23 reviews
From   US$ 108 /nightSelect
Not available
View on map9.8 mi from Cheshire9.8 mi from City Center
Set 25 minutes by foot from The Clark Art Institute, this comfortable hotel boasts a sun deck, a picnic area and a golf course available on site.
7.8
Very good43 reviews
From   US$ 69 /nightSelect
Not available
View on map12.1 mi from Cheshire12.1 mi from City Center
Opened in 1963, this pet-friendly accommodation includes a golf course and a garden, within 30 minutes' walk from the center of the city.
7.0
Very good19 reviews
From   US$ 73 /nightSelect
Not available
View on map6.7 mi from Cheshire6.7 mi from City Center
5.0
Guest rating10 reviews
From   US$ 79 /nightSelect
Not available
View on map9.7 mi from Cheshire9.7 mi from City Center
While staying in the hotel you are invited to discover The Clark Art Institute, set 25 minutes' stroll away, or Williams College Museum of Art, which is 1 miles away.
6.8
Nice92 reviews
From   US$ 94 /nightSelect
Not available
View on map12.3 mi from Cheshire12.3 mi from City Center
While staying in the hotel you are invited to discover Williams College, set in 2 miles away, or Pine Cobble Mountain, which is 2 miles away.
7.8
Very good29 reviews
From   US$ 79 /nightSelect
Not available
View on map9.3 mi from Cheshire9.3 mi from City Center
Just 0.6 miles away from Berkshire Museum, this hotel features a sun terrace and a golf course.
7.6
Very good9 reviews
From   US$ 110 /nightSelect
Not available
View on map9.3 mi from Cheshire9.3 mi from City Center
Featuring a seasonal outdoor swimming pool, a sun terrace and a shared lounge, this hotel is within 2 miles of Sweet Brook Farm.
7.4
Very good11 reviews
From   US$ 160 /nightSelect
Not available
View on map11.7 mi from Cheshire11.7 mi from City Center
Including a picnic area, the hotel's recreational facilities and entertainment activities along with an snack bar, the hotel is located in an skiing area close to a train station.
8.0
Great49 reviews
From   US$ 113 /nightSelect
Not available
View on map5.5 mi from Cheshire5.5 mi from City Center
While staying in the hotel you are invited to discover Berkshire Museum, set 15 minutes' ride away, or Lakeview Orchard, which is within 2 miles away.
From   US$ 50 /nightSelect
Not available
View on map4.0 mi from Cheshire4.0 mi from City Center
While staying in the hotel you are invited to discover Pontoosuc Lake, set in 2 miles away, or Lakeview Orchard, which is a 25-minute stroll away.
7.6
Very good2 reviews
From   US$ 119 /nightSelect
Not available
View on map7.0 mi from Cheshire7.0 mi from City Center
While staying in the hotel you are invited to discover Ioka Valley Farm, set a 15-minute ride away, or Ramblewild Adventure Park, which is in 3 miles away.
8.2
Great12 reviews
From   US$ 139 /nightSelect
Not available
View on map4.7 mi from Cheshire4.7 mi from City Center
Boasting a swimming pool, the hotel is about 20 minutes' walk from the center of New Ashford.
7.4
Very good7 reviews
From   US$ 140 /nightSelect
Not available
Bed & Breakfast
View on map4.7 mi from Cheshire4.7 mi from City Center
While staying in the hotel you are invited to discover Quaker Meeting House, set a mere 0.9 miles away, or Miss Adams Diner, which is just 5 minutes' walk away.
8.0
Great1 review
From   US$ 342 /nightSelect
Not available
View on map12.2 mi from Cheshire12.2 mi from City Center
Located 1 miles from Bousquet Ski Area, this comfortable hotel features 16 rooms, a garden, entertainment activities and various recreational opportunities.
6.0
Guest rating14 reviews
From   US$ 64 /nightSelect
Not available
View on map9.6 mi from Cheshire9.6 mi from City Center
While staying in the hotel you are invited to discover Williams College, set within 2 miles away, or Williams College Museum of Art, which is about 10 minutes by car.
Select
Not available
View on map9.6 mi from Cheshire9.6 mi from City Center
Featuring 36 rooms, a picnic area, a tennis court and a golf course, this venue is 5 minutes' drive from Hopkin's Memorial Forest in Williamstown.
7.8
Very good12 reviews
From   US$ 65 /nightSelect
Not available
View on map10.1 mi from Cheshire10.1 mi from City Center
While staying in the hotel you are invited to discover Bousquet Ski Area, set nearly a 25-minute stroll away, or Kirvin Park, which is 2 miles away.
9.2
Perfect9 reviews
From   US$ 267 /nightSelect
Not available
View on map10.0 mi from Cheshire10.0 mi from City Center
9.0
Perfect1 review
From   US$ 144 /nightSelect
Not available
View on map16.1 mi from Cheshire16.1 mi from City Center
Situated in an rural area of Lenox, this hotel features a library and a garden.
From   US$ 147 /nightSelect
Not available
Motel
View on map11.9 mi from Cheshire11.9 mi from City Center
This low-budget hotel with a swimming pool is about 15 minutes' drive from Ventfort Hall Mansion and Gilded Age Museum.
7.6
Very good21 reviews
From   US$ 56 /nightSelect
Not available
Bed & Breakfast
View on map9.8 mi from Cheshire9.8 mi from City Center
While staying in the hotel you are invited to discover Williams College Museum of Art, set around 10 minutes' drive away, or The Clark Art Institute, which is 2 miles away.
From   US$ 230 /nightSelect
Not available
View on map8.7 mi from Cheshire8.7 mi from City Center
From   US$ 299 /nightSelect
Not available
View on map10.6 mi from Cheshire10.6 mi from City Center
Located 0.3 miles from Hoosac Range Trail, the lodge features a sunbathing terrace and a picnic area.
From   US$ 170 /nightSelect
Not available
Bed & Breakfast
View on map10.8 mi from Cheshire10.8 mi from City Center
A victorian-style building was carefully renovated in 1760 and the lovely hotel is quite close to Hopkin's Memorial Forest.
8.0
Great7 reviews
From   US$ 138 /nightSelect
Not available
View on map6.7 mi from Cheshire6.7 mi from City Center
From   US$ 402 /nightSelect
Not available
View on map6.5 mi from Cheshire6.5 mi from City Center
From   US$ 154 /nightSelect
Not available
View on map6.5 mi from Cheshire6.5 mi from City Center
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Not available
View on map11.5 mi from Cheshire11.5 mi from City Center
From   US$ 148 /nightSelect
Not available
View on map6.5 mi from Cheshire6.5 mi from City Center
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View on map6.3 mi from Cheshire6.3 mi from City Center
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View on map10.9 mi from Cheshire10.9 mi from City Center
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View on map11.8 mi from Cheshire11.8 mi from City Center
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View on map4.1 mi from Cheshire4.1 mi from City Center
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View on map10.8 mi from Cheshire10.8 mi from City Center
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Not available
View on map6.5 mi from Cheshire6.5 mi from City Center
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View on map6.5 mi from Cheshire6.5 mi from City Center
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View on map8.0 mi from Cheshire8.0 mi from City Center
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Not available
View on map6.7 mi from Cheshire6.7 mi from City Center
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View on map6.7 mi from Cheshire6.7 mi from City Center
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View on map6.5 mi from Cheshire6.5 mi from City Center
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View on map6.5 mi from Cheshire6.5 mi from City Center
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View on map6.5 mi from Cheshire6.5 mi from City Center
From   US$ 211 /nightSelect
Not available
View on map6.5 mi from Cheshire6.5 mi from City Center
From   US$ 159 /nightSelect
Not available
View on map6.5 mi from Cheshire6.5 mi from City Center
From   US$ 159 /nightSelect
Not available
View on map4.3 mi from Cheshire4.3 mi from City Center
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Not available
View on map6.5 mi from Cheshire6.5 mi from City Center
The property provides a cash machine and a restaurant and is set 1.9 miles from the city center.
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Not available
View on map10.1 mi from Cheshire10.1 mi from City Center
Guests of this 2-bedroom property will benefit from the location in North Adams, as Sanford Blackinton Mansion is only 5 minutes' walk away.
From   US$ 427 /nightSelect
Not available
View on map6.3 mi from Cheshire6.3 mi from City Center
Ioka Valley Farm is 1.3 miles from this villa that offers 4 bedrooms along with a full kitchen.
From   US$ 557 /nightSelect
Not available
View on map9.4 mi from Cheshire9.4 mi from City Center
Set within walking distance of Unitarian Universalist Church of Pittsfield, this villa includes 5 bedrooms and a full kitchen for guests' convenience.
From   US$ 413 /nightSelect
Not available
View on map11.3 mi from Cheshire11.3 mi from City Center
From   US$ 204 /nightSelect
Not available
View on map7.1 mi from Cheshire7.1 mi from City Center
From   US$ 155 /nightSelect
Not available
View on map5.7 mi from Cheshire5.7 mi from City Center
Whitney's Farm Market & Garden Center is 2.9 miles from this villa that offers 3 bedrooms along with an equipped kitchen.
From   US$ 361 /nightSelect
Not available
View on map9.2 mi from Cheshire9.2 mi from City Center
Williams College Museum of Art is 1.4 miles from this villa that offers 3 bedrooms along with a full kitchen.
From   US$ 774 /nightSelect
Not available
View on map8.8 mi from Cheshire8.8 mi from City Center
Crane Museum of Papermaking is 6 miles from this villa that offers 3 bedrooms along with a full kitchen.
From   US$ 323 /nightSelect
Not available

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