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Best Cheshire MA hotels, motels and accommodations of 2020

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Harbour House Inn Cheshire725 North State Road, Cheshire, United StatesView on map
1.2 mi from City Center
Within easy reach of Rounds Rock, this hotel comprises 6 rooms with private bathrooms.
  • The bed & breakfast has
    • On-site car park
    +1
  • The bed & breakfast has
    • Coffee/Tea in lobby
    +1
Price fromUS$ 161per nightSelect
Not available
Similar properties near Cheshire
Jiminy Peak Mountain Resort Hancock37 Corey Rd, Hancock, United States, 01237View on map
6.7 mi from Cheshire
Located 3 km from the center of Hancock, the hotel offers a café bar plus a playroom, a playground and board games for children.
  • The resort has
    • Free Wi-Fi in rooms
    +1
  • The resort has
    • On-site car park
    +1
  • The resort has
    • 24-hour reception
    +1
7.6
Very good4 reviews
Price fromUS$ 429per nightSelect
Not available
The Porches Inn At Mass Moca231 River Street., North Adams, United States, 01247View on map
10.0 mi from Cheshire
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
Great10 reviews
Price fromUS$ 236per nightSelect
Not available
Hotel On North297 North Street, Pittsfield, United States, 01201View on map
8.9 mi from Cheshire
Offering convenient proximity to The Funky Phoenix, the hotel is also close to Herman Melville's Arrowhead.
Price fromUS$ 193per nightSelect
Not available
Holiday Inn & Suites Pittsfield-BerkshiresOne West Street, Pittsfield, United States, 01201View on map
9.1 mi from Cheshire
Situated in a shopping area of Pittsfield, this hotel features a tennis court and a golf course.
7.4
Very good36 reviews
Price fromUS$ 148per nightSelect
Not available
Wyndham Bentley Brook1 Corey Road, Hancock, United States, 01237View on map
6.6 mi from Cheshire
The hotel has to offer a spa centre and sauna rooms onsite along with 80 rooms, boasting setting in a resort area.
8.8
Great17 reviews
Price fromUS$ 378per nightSelect
Not available
Yankee Inn461 Pittsfield Road, Lenox, United States, 01240View on map
12.2 mi from Cheshire
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.
8.6
Great49 reviews
Price fromUS$ 93per nightSelect
Not available
Holiday Inn Berkshires40 Main Street, North Adams, United States, 01247View on map
9.8 mi from Cheshire
Featuring convenient access to Western Gateway Heritage State Park right in a ski area, this pleasant hotel provides a casino and a golf course.
7.2
Very good18 reviews
Price fromUS$ 162per nightSelect
Not available
Kemble Inn2 Kemble Street, Lenox, United States, 01240View on map
15.6 mi from Cheshire
The hotel offers 13 comfortable rooms and guests will be amazed at panoramic views of the city.
8.8
Great30 reviews
Price fromUS$ 415per nightSelect
Not available
Hampton Inn & Suites Berkshires Lenox445 Pittsfield Rd, Lenox, United States, 01240View on map
12.3 mi from Cheshire
The venue features a private pool and a local menu, while guests can take advantage of an ideal location in a busy area.
9.2
Perfect16 reviews
Price fromUS$ 212per nightSelect
Not available
Best Western Plus Berkshire Hills Inn & Suites1350 W Housatonic Street, Pittsfield, United States, 01201View on map
11.6 mi from Cheshire
There are rooms facing the courtyard and the hotel is set close to Bousquet Ski Area.
8.0
Great44 reviews
Price fromUS$ 126per nightSelect
Not available
Eastover Estate And Retreat430 East St P.O. Box 2282, Lenox, United States, 01240View on map
14.1 mi from Cheshire
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.
5.0
Guest rating1 review
Price fromUS$ 205per nightSelect
Not available
Garden Gables Inn135 Main St, Lenox, United States, 01240View on map
15.1 mi from Cheshire
The hotel is set close to Concepts of Art Lenox Judaica, and boasts a heated pool as well as terrace views.
9.0
Perfect30 reviews
Price fromUS$ 515per nightSelect
Not available
Vacation Village In The Berkshires276 Brodie Mountain Road, Hancock, United States, 01237View on map
6.5 mi from Cheshire
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 good195 reviews
Price fromUS$ 177per nightSelect
Not available
The Cornell Inn203 Main Street, Lenox, United States, 01240View on map
14.8 mi from Cheshire
The business hotel is a good starting point to Lenox' sights including Tanglewood Musical Center and Berkshire Horseback Adventures.
9.0
Perfect7 reviews
Price fromUS$ 234per nightSelect
Not available
Birchwood Inn7 Hubbard Street, Lenox, United States, 1240View on map
15.1 mi from Cheshire
This hotel features a shared lounge and a library, together with rooms overlooking the garden, and is located in a busy area.
Price fromUS$ 278per nightSelect
Not available
Gateways Inn & Restaurant51 Walker St, Lenox, United States, 01240-2719View on map
15.5 mi from Cheshire
The hotel offers easy access to Tanglewood Musical Center, boasting 11 rooms in the heart of Lenox.
Price fromUS$ 250per nightSelect
Not available
Hilton Garden Inn Lenox Pittsfield1032 South Street, Pittsfield, United States, 01201View on map
11.9 mi from Cheshire
Located near Bousquet Ski Area, the hotel offers sea views and an indoor pool.
Price fromUS$ 111per nightSelect
Not available
Econo Lodge16 Cheshire Road, Pittsfield, United States, 01201View on map
6.8 mi from Cheshire
Located in a ski area, the hotel has 58 rooms, and it features a motorway nearby.
4.2
Guest rating8 reviews
Price fromUS$ 102per nightSelect
Not available
The Rookwood Inn11 Old Stockbridge Road., Lenox, United States, 01240View on map
15.6 mi from Cheshire
Offering spectacular views of the garden, the hotel welcomes guests to the 24-hour restaurant that serves specialities of Japanese cuisine.
9.8
Perfect5 reviews
Price fromUS$ 241per nightSelect
Not available
The Village Inn16 Church St, Lenox, United States, 01240View on map
15.4 mi from Cheshire
Located 1 km from Lenox's city centre, this hotel boasts tasteful rooms and a private pool.
8.8
Great3 reviews
Price fromUS$ 143per nightSelect
Not available
Hampton Terrace Inn91 Walker St., Lenox, United States, 01240View on map
15.5 mi from Cheshire
The property features a library and tennis courts, guests can also savor their meals at the gourmet restaurant.
9.6
Perfect28 reviews
Price fromUS$ 205per nightSelect
Not available
Berkshire Mountain Lodge8 Dan Fox Drive, Pittsfield, United States, 01201View on map
11.7 mi from Cheshire
Situated 7 km from Lenox Mountain in Pittsfield, this property features an indoor pool and a golf course.
Price fromUS$ 128per nightSelect
Not available
Berkshire Inn150 W Housatonic St, Pittsfield, United States, 01201View on map
9.6 mi from Cheshire
This hotel features rooms with pool views, while a central location provides easy access to Bousquet Ski Area.
7.0
Very good40 reviews
Price fromUS$ 167per nightSelect
Not available
Brook Farm Inn15 Hawthorne Street, Lenox, United States, 01240View on map
15.8 mi from Cheshire
Located a few steps from The Bookstore, the hotel features 15 rooms with views over the city.
Price fromUS$ 271per nightSelect
Not available
Days Inn By Wyndham Lenox Ma194 Pittsfield Rd, Lenox, United States, 01240View on map
13.4 mi from Cheshire
This historic-style hotel is set at a short distance to Tanglewood.
6.8
Nice18 reviews
Price fromUS$ 198per nightSelect
Not available
Howard Johnson By Wyndham Lenox462 Pittsfield Road, Lenox, United States, 01240View on map
12.2 mi from Cheshire
Centrally located close to Pleasant Valley Sanctuary, this hotel in Lenox features a seasonal outdoor pool and a golf course.
7.6
Very good56 reviews
Price fromUS$ 140per nightSelect
Not available
Yankee Suites Extended Stay20 West Housatonic Street, Pittsfield, United States, 01201View on map
9.3 mi from Cheshire
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 good5 reviews
Price fromUS$ 148per nightSelect
Not available
Topia Inn - An Organic Oasis10 Pleasant Street, Adams, United StatesView on map
4.7 mi from Cheshire
The hotel is lodged in an organic-style building close to Mount Greylock, boasting 7 rooms, snow skiing, hiking and cycling.
Price fromUS$ 342per nightSelect
Not available
Lanesboro Country Inn499 South Main Street, Lanesborough, United StatesView on map
4.0 mi from Cheshire
Placed close to Mount Greylock State Reservation in the heart of Lanesborough, this hotel offers 9 rooms.
Price fromUS$ 117per nightSelect
Not available
Magnuson Hotel Lenox130 Pittsfield Rd., Lenox, United States, 01240View on map
13.7 mi from Cheshire
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
Price fromUS$ 103per nightSelect
Not available
Whistler'S Inn5 Greenwood Street, Lenox, United States, 01240View on map
15.1 mi from Cheshire
This hotel features rooms with forest views, while a convenient location provides easy access to Tanglewood.
7.4
Very good5 reviews
Price fromUS$ 225per nightSelect
Not available
Knights Inn Lenox474 Pittsfield Road, Lenox, United States, 01240View on map
12.1 mi from Cheshire
The hotel was built in 1972 in a ski area of Lenox, and nowadays has 16.
5.6
Guest rating10 reviews
Price fromUS$ 135per nightSelect
Not available
Wagon Wheel Inn484 Pittsfield Road, Lenox, United States, 01240View on map
12.1 mi from Cheshire
The hotel is located in the ski area of Lenox, not far away from Pleasant Valley Sanctuary, overlooking the city.
6.8
Nice30 reviews
Price fromUS$ 111per nightSelect
Not available
White Horse Inn378 South St, Pittsfield, United States, 01201View on map
10.1 mi from Cheshire
Bringing you close to Berkshire Museum, the hotel offers to try mountain biking, hiking and skiing and is nestled in a colonial-style building.
9.8
Perfect6 reviews
Price fromUS$ 267per nightSelect
Not available
Chesapeake Inn Of Lenox210 West Street, Lenox, United States, 01240View on map
16.0 mi from Cheshire
The hotel offers swift access to Tanglewood Musical Center and Tanglewood is only 250 meters away.
Price fromUS$ 199per nightSelect
Not available
Comfort Inn1055 South Street, Pittsfield, United States, 1201View on map
11.9 mi from Cheshire
Set in a ski area, this budget hotel has an outdoor swimming pool and 57 rooms within walking distance of Berkshire Museum.
7.2
Very good19 reviews
Price fromUS$ 95per nightSelect
Not available
Heart Of The Berkshires Motel970 W Housatonic St, Pittsfield, United StatesView on map
11.0 mi from Cheshire
This colonial-style hotel is set at a short distance to Fontaine's Auction Gallery.
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Not available
Econo Lodge The Springs94 Route 7, New Ashford, United States, 01237View on map
4.8 mi from Cheshire
Nestled 2 km from New Ashford city center, the hotel boasts a seasonal pool and a 24-hour bar.
Price fromUS$ 120per nightSelect
Not available
Redwood Motel915 State Road, North Adams, United States, 01247View on map
9.6 mi from Cheshire
A few meters away you can enjoy Chapin Library of Rare Books and Manuscripts.
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Not available
Whitcomb Summit Retreat229 Mohawk Trail, Florida, United States, 01247View on map
11.3 mi from Cheshire
Featuring 17 rooms, a patio and a picnic area, this venue is 10 minutes' drive from Massachusetts Museum of Contemporary Art in Florida.
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Not available
Lenox Inn525 Pittsfield Rd, Lenox, United States, 01240View on map
11.9 mi from Cheshire
Placed close to Canoe Meadows Wildlife Sanctuary in the centre of Lenox, this hotel offers 20 rooms.
7.6
Very good17 reviews
Price fromUS$ 56per nightSelect
Not available
The Summer White House17 Main St, Lenox, United States, 01240View on map
15.4 mi from Cheshire
Set in Lenox, this 6-room property is an ideal base for visits to The Mount, Edith Wharton's Home.
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Not available
Courtyard Lenox Berkshires70 Pittsfield Road, Lenox, United StatesView on map
13.9 mi from Cheshire
This hotel with 92 rooms and a lobby bar is centrally located 30 minutes' walk from the city center.
Price fromUS$ 313per nightSelect
Not available
Rose And Goat Retreat9 Moore'S Road, North Adams, United StatesView on map
11.4 mi from Cheshire
This spectacular villa in a mountain district has child care, a play area and a playground for kids.
Price fromUS$ 384per nightSelect
Not available
33 Main33 Main Street, Lenox, United States, MA 01240View on map
15.4 mi from Cheshire
The luxury hotel is a good starting point to Lenox' sights including Tanglewood and WAM Theatre.
Price fromUS$ 295per nightSelect
Not available
Apple Tree Inn10 Richmond Mountain Road, Lenox, United States, MA 01240View on map
16.4 mi from Cheshire
Located near Kripalu Center for Yoga and Health, the hotel offers mountain views and an outdoor pool.
Price fromUS$ 144per nightSelect
Not available
Mount Royal Inn99 Howland Ave, Adams, United States, MA 01220View on map
6.6 mi from Cheshire
Within easy reach of Real Eyes Gallery, this hotel comprises 16 rooms with private bathrooms.
Price fromUS$ 121per nightSelect
Not available
Blackinton Manor1391 Massachusetts Avenue, North Adams, United States, MA 01247View on map
9.8 mi from Cheshire
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.
Price fromUS$ 248per nightSelect
Not available
Tourists915 State Road, North Adams, United States, MA 01247View on map
9.6 mi from Cheshire
Located a few steps from The Clark Art Institute, the hotel features 48 rooms with views over the mountain.
Price fromUS$ 225per nightSelect
Not available
Americas Best Value Inn94 Route 7, New Ashford, United States, 01237View on map
4.1 mi from Cheshire
The hotel was built in 2009 in a historic area of New Ashford, and nowadays has 40.
Price fromUS$ 74per nightSelect
Not available
Berkshires Shirakaba20 Mallery Road, New Ashford, United States, 01237View on map
4.8 mi from Cheshire
9.6
Perfect19 reviews
Select
Not available
Thaddeus Clapp HouseWendell Avenue 74 74, Pittsfield, United States, 01201View on map
9.3 mi from Cheshire
Within easy reach of Berkshire Paint and Sip, this hotel comprises 8 rooms with private bathrooms.
9.2
Perfect4 reviews
Select
Not available
The Williams Inn101 Spring Street, Williamstown, United States, 01267View on map
10.4 mi from Cheshire
The accomodation is conveniently placed near Sheep Hill, offering 64 rooms along with a full service restaurant.
Price fromUS$ 245per nightSelect
Not available
Whistlers Inn Bed And Breakfast5 Greenwood Street, Lenox, United States, 01240View on map
15.0 mi from Cheshire
There are rooms facing the garden and the hotel is set close to Frelinghuysen Morris House & Studio.
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Not available
Fairfield Inn & Suites By Marriott Williamstown430 Main St, Williamstown, United States, 01267View on map
10.0 mi from Cheshire
Situated about 25 minutes' walk from The Clark Art Institute, the venue has 94 rooms with a scenic view of the landscape.
Price fromUS$ 192per nightSelect
Not available
Country Village At Jiminy Peak 37 Corey Road, , Hancock, United StatesView on map
6.5 mi from Cheshire
Offering snowboarding, snow skiing and bowling in the area, this accommodation lies next to Ioka Valley Farm, and within a 20-minute drive of Lakeview Orchard.
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Not available
Eastgate Inn207 West Street, Lenox, United StatesView on map
16.1 mi from Cheshire
This budget hotel with garden views lies close to the sights of Lenox including Lenox Mountain.
Price fromUS$ 147per nightSelect
Not available
The Springs Inn94 Route 7, New Ashford, United States, 01237View on map
5.6 mi from Cheshire
The hotel has a seasonal outdoor pool and lies close to Stony Ledge which is worth visiting.
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Not available
Knights Inn Lenox Ma474 Pittsfield Rd, Lenox, United States, 01240View on map
13.2 mi from Cheshire
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Not available
Guesthouse At Field Farm554 Sloan Road, Williamstown, United States, MA 01267View on map
8.7 mi from Cheshire
Located near Field Farm Reservation, the hotel offers mountain views and an outdoor pool.
Price fromUS$ 325per nightSelect
Not available
Tentrr A€“ Hidden Hoosic Riverside Camp525 East Road, Clarksburg, United States, 01247View on map
11.6 mi from Cheshire
Price fromUS$ 150per nightSelect
Not available
Tentrr - Round Mountain Campsite220 Round Mountain Road, Stephentown, United States, 12168View on map
9.1 mi from Cheshire
Price fromUS$ 123per nightSelect
Not available
Holiday Cottage636 S Main, Lanesborough, United States, 01237View on map
5.9 mi from Cheshire
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.
Price fromUS$ 633per nightSelect
Not available
Greylock Cottage636 S Main St, Lanesborough, United States, 01237View on map
5.9 mi from Cheshire
Berkshire Museum is 6 km from this villa that offers 4 bedrooms along with a kitchen.
Price fromUS$ 633per nightSelect
Not available
Tentrr - Birch Berry Pines232 Bailey Road, Lanesborough, United States, 01237View on map
4.7 mi from Cheshire
Price fromUS$ 135per nightSelect
Not available
Bentley Brook1 Corey Road, Hancock, United States, 01237View on map
6.4 mi from Cheshire
Select
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Writers Cottage636 South Main St, Lanesborough, United States, 01237View on map
5.9 mi from Cheshire
Offering a kitchen complete with a microwave oven, a dishwasher and kitchenware, this villa is located close to Imperial Bowl.
Price fromUS$ 487per nightSelect
Not available
Berkshire Cottage636 S Main St, Lanesborough, United States, 01237View on map
5.9 mi from Cheshire
Offering a full kitchen equipped with a refrigerator, a stove and kitchenware, this villa is set near Imperial Bowl.
Price fromUS$ 770per nightSelect
Not available
Tentrr - Living Water Campsites: Ski N' Zip 1Tamarack Road, Pittsfield, United States, 01201View on map
11.7 mi from Cheshire
Price fromUS$ 111per nightSelect
Not available
Tentrr - Living Water Campsites: Ski N' Zip 2Tamarack Road, Pittsfield, United States, 01201View on map
11.7 mi from Cheshire
Price fromUS$ 111per nightSelect
Not available
Updated Jiminy Peak Condo W/ Patio & Pool Access!Hancock, Ma, 01237, Hancock, United States, 01237View on map
6.8 mi from Cheshire
Offering a fully equipped kitchen complete with a microwave, a dishwasher and a fridge, this villa is located close to Ioka Valley Farm.
Price fromUS$ 347per nightSelect
Not available
Hancock Log Home - 2Mi To Jiminy Peak Resort!Hancock, Ma, 01237, Hancock, United States, 01237View on map
7.1 mi from Cheshire
Offering a fully equipped kitchen equipped with a microwave, coffee and tea making equipment and kitchenware, this villa is set near Rounds Mountain.
Price fromUS$ 222per nightSelect
Not available
Charming Berkshires Cottage On Ashmere LakeHinsdale, MA, 01235, Hinsdale, United States, 01235View on map
8.7 mi from Cheshire
Crane Museum of Papermaking is 6 miles from this villa that offers 3 bedrooms along with a full kitchen.
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Not available
Cozy Lenox Home 1.5 Mi. To Tanglewood Music!Lenox, MA, 01240, Lenox, United States, 01240View on map
15.5 mi from Cheshire
Stevens Glen is 4.5 miles from this villa that offers 3 bedrooms along with a kitchen.
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Not available
Lenox Home Mins To Tanglewood Shakespeare &CoLenox, MA, 01240, Lenox, United States, 01240View on map
13.3 mi from Cheshire
Church on the Hill is 1.8 miles from this villa that offers 3 bedrooms along with a fully equipped kitchen.
Price fromUS$ 280per nightSelect
Not available
Lake House W/ Deck & Views, Mins To Jiminy Peak!Lanesborough, MA, 01237, Lanesborough, United States, 01237View on map
5.9 mi from Cheshire
Lulu Cascade is 2.7 miles from this villa that offers 3 bedrooms along with a full kitchen.
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Not available
Family Home W/ Game Room - 3 Miles To Jiminy Peak!Lanesborough, MA, 01237, Lanesborough, United States, 01237View on map
4.5 mi from Cheshire
Offering a fully equipped kitchen equipped with a microwave oven, a dishwasher and a washing machine, this villa is set near Jiminy Peak Mountain Resort.
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Not available
Downtown Upstairs Lenox Suite C67 Church Street, Lenox, United States, MA 01240View on map
15.3 mi from Cheshire
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Downtown Upstairs Lenox Suite A26 Church Street Suite A, Lenox, United States, MA 01240View on map
15.4 mi from Cheshire
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Not available
Downtown Upstairs Lenox Suite B26 Church Street Suite B, Lenox, United States, MA 01240View on map
15.4 mi from Cheshire
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