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Cheshire (MA) hotels and places to stay

Search among 80 available hotels and places to stay in Cheshire from 50+ providers.

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26Jan2022Wednesday
27Jan2022Thursday
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  • The bed & breakfast has
    • Flat-screen TV
  • The bed & breakfast has
    • Ski storage
  • The bed & breakfast has
    • Hiking
    • Canoeing
    • Fishing
    • Skiing
View on map1.2 mi from City Center50 yd from City Center
Within easy reach of Rounds Rock, this hotel comprises 6 rooms with private bathrooms.
7.6
Very good4 reviews
From   US$ 200 /nightSelect
Not available
Similar properties near Cheshire
  • The hotel has
    • On-site car park
  • The hotel has
    • 24-hour reception
    • 24-hour security
View on map8.9 mi from Cheshire8.9 mi from City Center
Offering convenient proximity to The Funky Phoenix, the hotel is also close to Herman Melville's Arrowhead.
8.2
Great4 reviews
From   US$ 187 /nightSelect
Not available
View on map10.0 mi from Cheshire10.0 mi from City Center
Boasting location close to Massachusetts Museum of Contemporary Art, the venue features a heated outdoor pool and a library, as well as has to offer 47 rooms.
8.2
Great12 reviews
From   US$ 267 /nightSelect
Not available
View on map6.5 mi from Cheshire6.5 mi from City Center
The hotel has to offer a spa centre and sauna rooms onsite along with 80 rooms, boasting setting in a resort area.
8.6
Great27 reviews
From   US$ 513 /nightSelect
Not available
View on map11.7 mi from Cheshire11.7 mi from City Center
Situated 7 km from Lenox Mountain in Pittsfield, this property features an indoor pool and a golf course.
From   US$ 149 /nightSelect
Not available
View on map9.1 mi from Cheshire9.1 mi from City Center
Situated in a shopping area of Pittsfield, this hotel features a tennis court and a golf course.
7.4
Very good42 reviews
From   US$ 142 /nightSelect
Not available
View on map14.0 mi from Cheshire14.0 mi from City Center
This hotel with 92 rooms and a lobby bar is centrally located 30 minutes' walk from the city center.
7.6
Very good4 reviews
From   US$ 201 /nightSelect
Not available
Yankee InnHotel
View on map12.2 mi from Cheshire12.2 mi from City Center
At this venue, boasting a location in a ski area, guests can enjoy a shared lounge, a tennis court and a golf course, or explore Pittsfield Municipal Airport nearby.
8.4
Great63 reviews
From   US$ 111 /nightSelect
Not available
View on map10.0 mi from Cheshire10.0 mi from City Center
Featuring a private swimming pool and views of the sea, the property offers guests to enjoy contemporary meals and take advantage of its location in Williamstown.
8.4
Great17 reviews
From   US$ 238 /nightSelect
Not available
View on map6.7 mi from Cheshire6.7 mi from City Center
Located 3 km from the center of Hancock, the hotel offers a café bar plus a playroom, a playground and board games for children.
7.6
Very good8 reviews
From   US$ 429 /nightSelect
Not available
View on map6.5 mi from Cheshire6.5 mi from City Center
Situated 13 km from Mount Greylock in a ski district, this resort property features an indoor pool and an own patio with a great view.
7.8
Very good208 reviews
From   US$ 210 /nightSelect
Not available
View on map15.5 mi from Cheshire15.5 mi from City Center
The property features a library and tennis courts, guests can also savor their meals at the gourmet restaurant.
9.4
Perfect30 reviews
From   US$ 219 /nightSelect
Not available
View on map12.2 mi from Cheshire12.2 mi from City Center
Centrally located close to Pleasant Valley Sanctuary, this hotel in Lenox features a seasonal outdoor pool and a golf course.
7.6
Very good64 reviews
From   US$ 80 /nightSelect
Not available
View on map10.8 mi from Cheshire10.8 mi from City Center
Featuring a seasonal outdoor pool and a library, this hotel is adjacent to Williams College Museum of Art and 1 km from the city center.
7.4
Very good87 reviews
From   US$ 116 /nightSelect
Not available
The Cornell InnBed & Breakfast
View on map14.8 mi from Cheshire14.8 mi from City Center
The business hotel is a good starting point to Lenox' sights including Tanglewood Musical Center and Berkshire Horseback Adventures.
8.8
Great14 reviews
From   US$ 195 /nightSelect
Not available
View on map10.1 mi from Cheshire10.1 mi from City Center
Located next to Williams College, the venue comprises 17 rooms with garden views.
8.6
Great33 reviews
From   US$ 108 /nightSelect
Not available
View on map12.3 mi from Cheshire12.3 mi from City Center
The venue features a private pool and a local menu, while guests can take advantage of an ideal location in a busy area.
9.0
Perfect25 reviews
From   US$ 129 /nightSelect
Not available
View on map13.4 mi from Cheshire13.4 mi from City Center
This historic-style hotel is set at a short distance to Tanglewood.
6.8
Nice21 reviews
From   US$ 138 /nightSelect
Not available
View on map6.8 mi from Cheshire6.8 mi from City Center
Located in a ski area, the hotel has 58 rooms, and it features a motorway nearby.
5.0
Guest rating10 reviews
From   US$ 71 /nightSelect
Not available
View on map10.8 mi from Cheshire10.8 mi from City Center
Based in the colonial-style building in the heart of Williamstown, this hotel boasts the Colonial décor in 124 rooms along with an indoor pool onsite.
7.8
Very good90 reviews
From   US$ 182 /nightSelect
Not available
View on map11.9 mi from Cheshire11.9 mi from City Center
Located near Bousquet Ski Area, the hotel offers sea views and an indoor pool.
7.6
Very good2 reviews
From   US$ 203 /nightSelect
Not available
View on map10.2 mi from Cheshire10.2 mi from City Center
The budget hotel is located in a mountain area with quick access to The Clark Art Institute.
8.0
Great8 reviews
From   US$ 95 /nightSelect
Not available
View on map9.8 mi from Cheshire9.8 mi from City Center
Featuring convenient access to Western Gateway Heritage State Park right in a ski area, this pleasant hotel provides a casino and a golf course.
7.4
Very good21 reviews
From   US$ 149 /nightSelect
Not available
View on map9.7 mi from Cheshire9.7 mi from City Center
This hotel offers the lobby bar and 35 rooms together with major location close to The Clark Art Institute.
6.8
Nice92 reviews
From   US$ 83 /nightSelect
Not available
Kemble InnHotel
View on map15.6 mi from Cheshire15.6 mi from City Center
The hotel offers 13 comfortable rooms and guests will be amazed at panoramic views of the city.
8.8
Great35 reviews
From   US$ 146 /nightSelect
Not available
View on map12.1 mi from Cheshire12.1 mi from City Center
The hotel is located in the ski area of Lenox, not far away from Pleasant Valley Sanctuary, overlooking the city.
7.0
Very good34 reviews
From   US$ 63 /nightSelect
Not available
View on map10.4 mi from Cheshire10.4 mi from City Center
The accomodation is conveniently placed near Sheep Hill, offering 64 rooms along with a full service restaurant.
8.4
Great1 review
From   US$ 320 /nightSelect
Not available
View on map12.1 mi from Cheshire12.1 mi from City Center
Providing access to Taconic Trail State Park, this hotel is a 30-minute walk from Williams College and offers a garden restaurant.
6.8
Nice15 reviews
From   US$ 72 /nightSelect
Not available
Gateways Inn & RestaurantBed & Breakfast
View on map15.5 mi from Cheshire15.5 mi from City Center
The hotel offers easy access to Tanglewood Musical Center, boasting 11 rooms in the heart of Lenox.
8.0
Great3 reviews
From   US$ 252 /nightSelect
Not available
Rookwood InnBed & Breakfast
View on map15.6 mi from Cheshire15.6 mi from City Center
Offering spectacular views of the garden, the hotel welcomes guests to the 24-hour restaurant that serves specialities of Japanese cuisine.
8.8
Great10 reviews
From   US$ 361 /nightSelect
Not available
View on map12.3 mi from Cheshire12.3 mi from City Center
Located a few steps from The Clark Art Institute, the hotel features 13 rooms with views over the garden.
7.8
Very good21 reviews
From   US$ 86 /nightSelect
Not available
View on map9.3 mi from Cheshire9.3 mi from City Center
Constructed in 1982 year, the hotel's building is a reminder of a colonial style, located just off Canoe Meadows Wildlife Sanctuary.
7.6
Very good9 reviews
From   US$ 188 /nightSelect
Not available
View on map14.1 mi from Cheshire14.1 mi from City Center
Boasting a library, a tennis court and a golf course, the venue with breathtaking views offers 65 rooms in proximity to Ventfort Hall Mansion and Gilded Age Museum.
7.6
Very good4 reviews
From   US$ 444 /nightSelect
Not available
Birchwood InnBed & Breakfast
View on map15.0 mi from Cheshire15.0 mi from City Center
This hotel features a shared lounge and a library, together with rooms overlooking the garden, and is located in a busy area.
7.8
Very good11 reviews
From   US$ 188 /nightSelect
Not available
TouristsHotel
View on map9.6 mi from Cheshire9.6 mi from City Center
Located a few steps from The Clark Art Institute, the hotel features 48 rooms with views over the mountain.
From   US$ 280 /nightSelect
Not available
View on map9.6 mi from Cheshire9.6 mi from City Center
This hotel features rooms with pool views, while a central location provides easy access to Bousquet Ski Area.
7.0
Very good47 reviews
From   US$ 90 /nightSelect
Not available
View on map15.1 mi from Cheshire15.1 mi from City Center
There are rooms facing the garden and the hotel is set close to Frelinghuysen Morris House & Studio.
Select
Not available
Brook Farm InnBed & Breakfast
View on map15.8 mi from Cheshire15.8 mi from City Center
Located a few steps from The Bookstore, the hotel features 15 rooms with views over the city.
8.2
Great
From   US$ 225 /nightSelect
Not available
View on map11.7 mi from Cheshire11.7 mi from City Center
There are rooms facing the courtyard and the hotel is set close to Bousquet Ski Area.
8.0
Great45 reviews
From   US$ 158 /nightSelect
Not available
View on map16.4 mi from Cheshire16.4 mi from City Center
Located near Kripalu Center for Yoga and Health, the hotel offers mountain views and an outdoor pool.
6.4
Nice3 reviews
From   US$ 142 /nightSelect
Not available
View on map9.3 mi from Cheshire9.3 mi from City Center
Featuring convenient access to Williams College right in a mountain area, this designer hotel provides a sun deck, an outdoor pool area and a shared lounge.
6.8
Nice7 reviews
From   US$ 144 /nightSelect
Not available
View on map5.5 mi from Cheshire5.5 mi from City Center
Located next to Skyline Country Club, the venue comprises 13 rooms with garden views.
From   US$ 50 /nightSelect
Not available
View on map9.8 mi from Cheshire9.8 mi from City Center
Offering snow skiing and hiking in the area, this accommodation lies next to Williams College Museum of Art, and within a 40-minute drive of Jiminy Peak Mountain Resort.
7.8
Very good37 reviews
From   US$ 89 /nightSelect
Not available
View on map4.0 mi from Cheshire4.0 mi from City Center
Placed close to Mount Greylock State Reservation in the heart of Lanesborough, this hotel offers 9 rooms.
7.6
Very good2 reviews
From   US$ 119 /nightSelect
Not available
View on map7.0 mi from Cheshire7.0 mi from City Center
Located a few steps from Ramblewild Adventure Park, the hotel features 16 rooms with views over the mountain.
8.2
Great12 reviews
From   US$ 154 /nightSelect
Not available
View on map4.7 mi from Cheshire4.7 mi from City Center
The hotel is lodged in an organic-style building close to Mount Greylock, boasting 7 rooms, snow skiing, hiking and cycling.
8.0
Great1 review
From   US$ 342 /nightSelect
Not available
View on map12.2 mi from Cheshire12.2 mi from City Center
The hotel was built in 1972 in a ski area of Lenox, and nowadays has 16.
6.0
Guest rating14 reviews
From   US$ 86 /nightSelect
Not available
View on map9.6 mi from Cheshire9.6 mi from City Center
A few meters away you can enjoy Chapin Library of Rare Books and Manuscripts.
Select
Not available
View on map9.6 mi from Cheshire9.6 mi from City Center
Boasting location close to The Clark Art Institute, the venue includes 30 rooms and a heated pool.
8.0
Great10 reviews
From   US$ 122 /nightSelect
Not available
View on map6.6 mi from Cheshire6.6 mi from City Center
Within easy reach of Real Eyes Gallery, this hotel comprises 16 rooms with private bathrooms.
8.0
Great1 review
From   US$ 144 /nightSelect
Not available
33 MainInn
View on map15.4 mi from Cheshire15.4 mi from City Center
The luxury hotel is a good starting point to Lenox' sights including Tanglewood and WAM Theatre.
7.6
Very good4 reviews
From   US$ 346 /nightSelect
Not available
View on map10.1 mi from Cheshire10.1 mi from City Center
Bringing you close to Berkshire Museum, the hotel offers to try mountain biking, hiking and skiing and is nestled in a colonial-style building.
9.2
Perfect9 reviews
From   US$ 267 /nightSelect
Not available
Lenox InnMotel
View on map11.9 mi from Cheshire11.9 mi from City Center
Placed close to Canoe Meadows Wildlife Sanctuary in the centre of Lenox, this hotel offers 20 rooms.
7.6
Very good21 reviews
From   US$ 56 /nightSelect
Not available
View on map10.0 mi from Cheshire10.0 mi from City Center
Situated about 25 minutes' walk from The Clark Art Institute, the venue has 94 rooms with a scenic view of the landscape.
9.0
Perfect1 review
From   US$ 220 /nightSelect
Not available
Whistler'S InnBed & Breakfast
View on map15.1 mi from Cheshire15.1 mi from City Center
This hotel features rooms with forest views, while a convenient location provides easy access to Tanglewood.
7.8
Very good11 reviews
From   US$ 230 /nightSelect
Not available
View on map15.5 mi from Cheshire15.5 mi from City Center
Located just off Lenox Parks and Recreation Dept and 1.6 miles from The Mount, Edith Wharton's Home, this hotel features evening entertainment activities and a bar.
From   US$ 179 /nightSelect
Not available
View on map13.7 mi from Cheshire13.7 mi from City Center
Close to Ventfort Hall Mansion and Gilded Age Museum in Lenox, the comfortable hotel is lodged in a historic-style building and consists of 52 rooms.
7.0
Very good18 reviews
From   US$ 64 /nightSelect
Not available
View on map16.1 mi from Cheshire16.1 mi from City Center
This budget hotel with garden views lies close to the sights of Lenox including Lenox Mountain.
From   US$ 147 /nightSelect
Not available
Blackinton ManorBed & Breakfast
View on map9.8 mi from Cheshire9.8 mi from City Center
Offering hiking and fisheries in the area, this accommodation lies next to MASS MoCA, and within a 10-minute drive of Western Gateway Heritage State Park.
From   US$ 280 /nightSelect
Not available
Guesthouse At Field FarmBed & Breakfast
View on map8.7 mi from Cheshire8.7 mi from City Center
Located near Field Farm Reservation, the hotel offers mountain views and an outdoor pool.
From   US$ 269 /nightSelect
Not available
View on map4.7 mi from Cheshire4.7 mi from City Center
Nestled 2 km from New Ashford city center, the hotel boasts a seasonal pool and a 24-hour bar.
7.8
Very good3 reviews
From   US$ 120 /nightSelect
Not available
House On Main StreetBed & 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 map5.9 mi from Cheshire5.9 mi from City Center
Offering a full kitchen complete with a microwave oven, a dishwasher and a toaster, this villa is located close to Regal Cinema at Berkshire Mall.
From   US$ 633 /nightSelect
Not available
View on map13.3 mi from Cheshire13.3 mi from City Center
Church on the Hill is 1.8 miles from this villa that offers 3 bedrooms along with a fully equipped kitchen.
From   US$ 253 /nightSelect
Not available
View on map4.7 mi from Cheshire4.7 mi from City Center
From   US$ 150 /nightSelect
Not available
View on map14.3 mi from Cheshire14.3 mi from City Center
From   US$ 499 /nightSelect
Not available
View on map13.6 mi from Cheshire13.6 mi from City Center
Set within walking distance of Richmond Pond Town Beach, this villa includes 2 bedrooms and a kitchen for guests' convenience.
Select
Not available
View on map15.3 mi from Cheshire15.3 mi from City Center
This 81 m² apartment gives direct access to DeVries Fine Art International Inc and comprises 2 bedrooms.
From   US$ 494 /nightSelect
Not available
View on map15.4 mi from Cheshire15.4 mi from City Center
From   US$ 308 /nightSelect
Not available
View on map7.1 mi from Cheshire7.1 mi from City Center
From   US$ 157 /nightSelect
Not available
View on map5.9 mi from Cheshire5.9 mi from City Center
Offering a full kitchen equipped with a refrigerator, a stove and kitchenware, this villa is set near Imperial Bowl.
From   US$ 748 /nightSelect
Not available
View on map5.9 mi from Cheshire5.9 mi from City Center
Offering a kitchen complete with a microwave oven, a dishwasher and kitchenware, this villa is located close to Imperial Bowl.
From   US$ 483 /nightSelect
Not available
View on map5.9 mi from Cheshire5.9 mi from City Center
Berkshire Museum is 6 km from this villa that offers 4 bedrooms along with a kitchen.
From   US$ 633 /nightSelect
Not available
View on map4.7 mi from Cheshire4.7 mi from City Center
This is a 1-bedroom villa, set in proximity to Ioka Valley Farm.
From   US$ 129 /nightSelect
Not available
View on map7.1 mi from Cheshire7.1 mi from City Center
Offering a fully equipped kitchen equipped with a microwave, coffee and tea making equipment and kitchenware, this villa is set near Rounds Mountain.
From   US$ 214 /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.
Select
Not available
View on map15.5 mi from Cheshire15.5 mi from City Center
Stevens Glen is 4.5 miles from this villa that offers 3 bedrooms along with a kitchen.
From   US$ 512 /nightSelect
Not available
View on map12.2 mi from Cheshire12.2 mi from City Center
Located about 2.6 miles from Pleasant Valley Sanctuary, the villa offers accommodation for 6 guests.
Select
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$ 749 /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$ 537 /nightSelect
Not available

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