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Best Sheffield MA hotels, motels and accommodations of 2020

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Staveleigh House Bed And Breakfast SheffieldBed & Breakfast59 Main St., Sheffield, United States, MA 01257View on map
The hotel is based in a historic-style building located in the old part of Sheffield, offering 7 rooms.
  • The bed & breakfast has
    • Flat-screen TV
    +1
Price fromUS$ 165per nightSelect
Not available
Sheffield 1802 House Bed & BreakfastBed & Breakfast48 South Main Street, Sheffield, United States, MA 01257View on map
There are rooms facing the garden and the hotel is set close to Berkshire Mountain Distillers.
  • The bed & breakfast has
    • Outdoor dining area
    +1
Price fromUS$ 150per nightSelect
Not available
Similar properties near Sheffield
Canyon Ranch Lenox165 Kemble St, Lenox, United States, 01240View on map
17.1 mi from Sheffield
Featuring a seasonal outdoor pool, an indoor swimming pool and tennis courts, the hotel offers a lovely accommodation just outside Tanglewood Musical Center.
8.6
Great19 reviews
Price fromUS$ 2 861per nightSelect
Not available
Cranwell Spa And Golf Resort55 Lee Road, Lenox, United States, 01240View on map
17.1 mi from Sheffield
The hotel has an award-winning restaurant plus 114 rooms and is located in a historic area.
7.8
Very good14 reviews
Price fromUS$ 139per nightSelect
Not available
The Red Lion Inn30 Main Street, Stockbridge, United States, 01262-0954View on map
12.5 mi from Sheffield
A casual restaurant and 108 rooms are available during the stay in charming hotel, boasting location next to Chesterwood Museum.
8.2
Great45 reviews
Price fromUS$ 255per nightSelect
Not available
Blantyre16 Blantyre Rd , Lenox, United States, 01240View on map
16.8 mi from Sheffield
Set in Lenox, this accommodation features an outdoor swimming pool and a garden.
9.0
Perfect24 reviews
Price fromUS$ 1 425per nightSelect
Not available
The Old Inn On The Green134 Hartsville New Marlborough Rd, New Marlborough, United StatesView on map
6.5 mi from Sheffield
This hotel features rooms with pool views, while a great location provides easy access to Campbell Falls.
Price fromUS$ 402per nightSelect
Not available
The Barrington281 Main St., Great Barrington, United StatesView on map
6.3 mi from Sheffield
There are rooms facing the mountain and the hotel is set close to Lake Mansfield.
Price fromUS$ 273per nightSelect
Not available
Wheatleigh11 Hawthorne Road, Lenox, United States, 01240View on map
16.7 mi from Sheffield
Located 3 km from Lenox's city centre, this hotel boasts non-smoking rooms and a seasonal outdoor pool.
9.2
Perfect12 reviews
Price fromUS$ 1 317per nightSelect
Not available
The Black Swan Lee - Lenox, Ascend Hotel Collection435 Laurel Street, Lee, United States, 01238View on map
15.8 mi from Sheffield
Offering 52 rooms as well as a gym area and a fitness centre, this venue overlooks Laurel Lake and is based in a recreational area.
7.4
Very good21 reviews
Price fromUS$ 194per nightSelect
Not available
Interlaken Inn & Resort74 Interlaken Road, Lakeville, United States, CT 06039View on map
11.8 mi from Sheffield
Featuring a swimming pool, this impressive venue is situated within 20 minutes' walk of the city center.
7.2
Very good19 reviews
Price fromUS$ 238per nightSelect
Not available
Devonfield Inn85 Stockbridge Rd., Lee, United States, 01238View on map
14.4 mi from Sheffield
Located 2 km away from Lee city center, this hotel features 10 rooms and an outdoor pool.
9.6
Perfect3 reviews
Price fromUS$ 202per nightSelect
Not available
The Inn At Stockbridge30 East Street, Stockbridge, United States, 01262View on map
13.9 mi from Sheffield
Within easy reach of Norman Rockwell Museum, this hotel comprises 15 rooms with en suite bathrooms.
8.4
Great6 reviews
Price fromUS$ 265per nightSelect
Not available
Chambery Inn199 Main St., Lee, United States, 1238View on map
15.1 mi from Sheffield
Offering convenient proximity to Hats & Jewels, the hotel is also close to Congregational Church.
9.2
Perfect23 reviews
Price fromUS$ 277per nightSelect
Not available
Fairfield Inn & Suites Great Barrington Lenox/Berk249 Stockbridge Road, Route 7, Great Barrington, United States, 01230View on map
7.2 mi from Sheffield
Featuring an indoor swimming pool and a picnic area as well as a heated pool, the hotel is situated in the centre of Great Barrington.
8.0
Great40 reviews
Price fromUS$ 277per nightSelect
Not available
Holiday Inn Express Great Barrington415 Stockbridge Road, Great Barrington, United States, 01230View on map
7.6 mi from Sheffield
Offering hiking and lawn tennis in the area, this accommodation lies next to Lake Mansfield, and within a 40-minute drive of Tanglewood.
8.0
Great7 reviews
Price fromUS$ 189per nightSelect
Not available
The Briarcliff Motel506 Stockbridge Road, Great Barrington, United States, 01230View on map
9.5 mi from Sheffield
The hotel is located in the ski area of Great Barrington, not far away from Monument Mountain, overlooking the mountain.
9.6
Perfect40 reviews
Price fromUS$ 170per nightSelect
Not available
Days Inn By Wyndham Great Barrington372 Main Street, Great Barrington, United States, 01230View on map
6.2 mi from Sheffield
This budget hotel with city views lies close to the sights of Great Barrington including Lake Mansfield.
7.6
Very good26 reviews
Price fromUS$ 127per nightSelect
Not available
Shaker Mill Inn7 Albany Road, West Stockbridge, United States, 01266View on map
16.1 mi from Sheffield
Within easy reach of Diana Felber Gallery, this hotel comprises 9 rooms with private bathrooms.
9.8
Perfect5 reviews
Price fromUS$ 201per nightSelect
Not available
Monument Mountain Motel247 Stockbridge Road, Great Barrington, United States, 01230View on map
7.2 mi from Sheffield
This central hotel is nestled in the heart of Great Barrington, not far from Lake Mansfield.
9.4
Perfect37 reviews
Price fromUS$ 146per nightSelect
Not available
Fairfield Inn & Suites By Marriott Great Barrington Lenox/Berkshires249 Stockbridge Rd, Great Barrington, United StatesView on map
7.2 mi from Sheffield
This family-friendly hotel is nestled in the heart of Great Barrington, not far from Fairview Hospital.
Price fromUS$ 134per nightSelect
Not available
The Egremont Village Inn17 Main Street, South Egremont, United States, 01258View on map
5.0 mi from Sheffield
Located 1 km from the center of South Egremont, this hotel features snow skiing, horse riding and hiking in the area and a snack bar onsite.
Price fromUS$ 184per nightSelect
Not available
Thornewood Inn453 Stockbridge Road, Great Barrington, United States, 01230View on map
8.3 mi from Sheffield
Offering hills views, the venue is placed close to Lake Mansfield, and boasts an outdoor pool.
8.2
Great18 reviews
Price fromUS$ 232per nightSelect
Not available
Federal House Inn1560 Pleasant Street, Lee, United States, 1260View on map
12.6 mi from Sheffield
Located next to Lee Premium Outlets, the venue comprises 9 rooms with garden views.
Price fromUS$ 336per nightSelect
Not available
1862 Seasons On Main B And B47 Main Street, Stockbridge, United States, 01262View on map
12.5 mi from Sheffield
Every room welcomes with a lovely view and the hotel features a picnic area and barbeque grills, while the hotel is set close to Norman Rockwell Museum.
Price fromUS$ 185per nightSelect
Not available
Stockbridge Country Inn (Adults Only)26 Glendale Road, Stockbridge, United States, 01262View on map
12.4 mi from Sheffield
Situated next to The Mission House in Stockbridge, this hotel features an outdoor swimming pool and offers guests to admire a sweeping view.
9.4
Perfect17 reviews
Price fromUS$ 264per nightSelect
Not available
Pilgrim Inn165 Housatonic Street, Lee, United States, 01238View on map
14.8 mi from Sheffield
Boasting setting next to October Mountain State Forest, this central property offers a heated pool onsite as well as child care and a mini club for children.
7.0
Very good11 reviews
Price fromUS$ 121per nightSelect
Not available
Super 8 By Wyndham Lee/Berkshires/Outlet Area170 Housatonic Street, Lee, United States, 01238View on map
14.8 mi from Sheffield
The hotel offers a business accommodation with 49 rooms in the mountain area of Lee.
8.2
Great6 reviews
Price fromUS$ 111per nightSelect
Not available
Windflower Inn684 South Egremont Road, Great Barrington, United States, 01230View on map
5.1 mi from Sheffield
Offering a seasonal outdoor swimming pool, the hotel is placed in the ski area of Great Barrington, just off Vault Gallery.
Price fromUS$ 186per nightSelect
Not available
Rodeway Inn200 Laurel St, Lee, United States, 01238View on map
15.5 mi from Sheffield
In the vicinity of this contemporary there is October Mountain State Forest and guests can also discover the natural area.
6.4
Nice11 reviews
Price fromUS$ 72per nightSelect
Not available
Mountain View Motel - Great Barrington304 State Road, Great Barrington, United States, 01230View on map
6.3 mi from Sheffield
Located 3 km from the center of Great Barrington, the hotel offers a 24-hour bar plus a playground and a play area for children.
Price fromUS$ 99per nightSelect
Not available
Locust Tree Bed And Breakfast131 East Canaan Rd, Canaan, United States, 6018View on map
6.4 mi from Sheffield
A short walk from Beckley Furnace Industrial Monument, the property welcomes guests to the family restaurant on site.
Price fromUS$ 146per nightSelect
Not available
Sunset Inn150 Housatonic Street, Lee, United States, 01238View on map
14.8 mi from Sheffield
An outdoor pool area and a picnic area are offered to guests of the central hotel located in the heart of Lee.
Price fromUS$ 157per nightSelect
Not available
Econo Lodge Lee - Great Barrington980 Pleasant Street, Lee, United States, 01238View on map
13.0 mi from Sheffield
Close to AniMagic in Lee, the pet-friendly hotel is lodged in a historic-style building and consists of 28 rooms.
7.6
Very good25 reviews
Price fromUS$ 88per nightSelect
Not available
Applegate Inn279 West Park St., Lee, United States, 01238View on map
14.5 mi from Sheffield
Boasting access to Twisted Orchard Company, the hotel includes a library and tennis courts onsite providing guests with en-suite rooms.
Price fromUS$ 210per nightSelect
Not available
Travelodge By Wyndham Great Barrington Berkshires400 Stockbridge Road, Great Barrington, United States, 01230View on map
7.5 mi from Sheffield
Just off Lake Mansfield, this hotel offers a convenient location and includes a fast food restaurant.
7.2
Very good8 reviews
Price fromUS$ 156per nightSelect
Not available
Lantern House Motel256 Stockbridge Road, Great Barrington, United StatesView on map
7.3 mi from Sheffield
Located near Lake Mansfield, the hotel offers garden views and an outdoor pool.
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Not available
Chestnut Lodge75 Chestnut Street, Lee, United StatesView on map
15.8 mi from Sheffield
Featuring a kitchen and a terrace, the property is a 25-minute drive from Pittsfield airport.
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Not available
The Ponds At Foxhollow 4 Foxhollow Drive, , Lenox, United StatesView on map
15.7 mi from Sheffield
The hotel has a lobby restaurant as well as an indoor pool, available in the heart of Lenox.
Price fromUS$ 231per nightSelect
Not available
The White Hart15 Undermountain Road, Salisbury, United States, CT 06068View on map
8.9 mi from Sheffield
Located a few steps from Holley-Williams House, the hotel features 16 rooms with views over the city.
Price fromUS$ 392per nightSelect
Not available
Seven Hills Inn40 Plunkett St, Lenox, United States, 01240-2704View on map
16.5 mi from Sheffield
There are rooms facing the garden and the hotel is set close to Tanglewood Musical Center.
Price fromUS$ 132per nightSelect
Not available
Lakehouse Inn615 Laurel St., Lee, United States, MA 01238View on map
16.1 mi from Sheffield
The luxury hotel boasts 15 rooms along with canoeing, hiking and fisheries, offering direct access to AniMagic.
Price fromUS$ 262per nightSelect
Not available
The Cottage14 Prospect Hill Road, Stockbridge, United States, 01262View on map
13.8 mi from Sheffield
Situated close to Norman Rockwell Museum, this hotel in Stockbridge features tennis courts and a golf course.
Price fromUS$ 241per nightSelect
Not available
Wainwright Inn518 Main Street, Great Barrington, United States, MA 01230View on map
5.8 mi from Sheffield
Located next to The Guthrie Center & Foundation, the venue comprises 9 rooms with garden views.
Price fromUS$ 244per nightSelect
Not available
Holiday Inn Club Vacations Oak N' Spruce Resort190 Meadow Street, Lee, United States, MA 01260View on map
12.5 mi from Sheffield
Featuring 334 rooms, a nightclub, a private swimming pool and a picnic area, this venue is 130 minutes' drive from Living Museum in Lee.
Price fromUS$ 211per nightSelect
Not available
Conroy'S B&B11 East Street, Stockbridge, United States, 01262View on map
13.9 mi from Sheffield
Featuring a library and a tennis court, this hotel is just 2.6 km from The Mission House.
Price fromUS$ 189per nightSelect
Not available
Inn At Iron Masters229 Main Street, Lakeville, United StatesView on map
10.0 mi from Sheffield
Located next to Lions Head, the venue comprises 28 rooms with city views.
Price fromUS$ 172per nightSelect
Not available
Swiss Hutte Inn And Restaurant3290 State Route 23 P.O. Box 357, Hillsdale, United States, NY 12529View on map
8.0 mi from Sheffield
Located very close to Catamount Mountain Resort, this hotel features 14 rooms together with a garden restaurant.
Price fromUS$ 153per nightSelect
Not available
Mountain View Green Retreat67 Litchfield Road, Norfolk, United States, CT 06058View on map
11.4 mi from Sheffield
This historical hotel with park views lies close to the sights of Norfolk including St. Paul's Episcopal Church.
Price fromUS$ 153per nightSelect
Not available
Silvanus Lodge9350 State Route 22, Hillsdale, United States, 12529View on map
10.1 mi from Sheffield
Offering 9 rooms together with horse riding, hiking and fisheries, the venue is located close to Roeliff Jansen Park.
Price fromUS$ 107per nightSelect
Not available
Wind In The Pines 949 S. Main St., , Great Barrington, United StatesView on map
4.6 mi from Sheffield
Located just off Ski Butternut, this hotel provides a wellness area, a spa area and a sauna onsite.
Price fromUS$ 854per nightSelect
Not available
Stonegate 111 West Ave., , Great Barrington, United States, 01230View on map
5371.5 mi from Sheffield
Offering water skiing, snow skiing and archery onsite, this hotel boasts a great location close to W.E.B. DuBois Birthplace reachable on foot.
Price fromUS$ 70per nightSelect
Not available
The Inn At Sweet Water FarmProspect Lake Road 1 1, South Egremont, United States, 01230View on map
7.8 mi from Sheffield
The charming hotel is a good starting point to South Egremont' sights including Catamount Mountain Resort and French Park.
9.4
Perfect23 reviews
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Not available
The Red Door B&B55 Cliffwood St, Lee, United States, 01238View on map
15.2 mi from Sheffield
Price fromUS$ 175per nightSelect
Not available
American Inn200 Laurel Street P O Box 492, Lee, United States, MA 01238View on map
15.6 mi from Sheffield
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Not available
Shaker Mill InnOak Street ,2 , Lenox, United States, MA 01266View on map
16.0 mi from Sheffield
Within easy reach of The Foundry, this hotel comprises 9 rooms with private bathrooms.
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Not available
Manor House Inn69 Maple Ave, Norfolk, United States, CT 06058View on map
11.2 mi from Sheffield
Just 2 km from Haystack Mountain State Park, the hotel boasts a playroom and board games for children and includes 9 rooms.
Price fromUS$ 169per nightSelect
Not available
The Inn At White Hollow Farm558 Lime Rock Road, Salisbury, United States, CT 06039View on map
11.8 mi from Sheffield
The hotel is based in a ski area of Salisbury, offering a lounge bar along with canoeing, horse riding and hiking.
Price fromUS$ 244per nightSelect
Not available
Holiday Inn Express Hotel & Suites Great Barrington415 Stockbridge Rd, Great Barrington, United States, 01230View on map
8.8 mi from Sheffield
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Not available
Gedney Farm34 Hartsville-New Marlborough Road, New Marlborough, United States, MA 01230View on map
6.7 mi from Sheffield
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Not available
The Tower Unit70 Franklin Street, Lee, United StatesView on map
15.1 mi from Sheffield
Featuring a kitchen, the venue is only 1.8 miles from Laurel Lake.
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Not available
1862 Seasons On Main Bed And Breakfast47 Main Street, Stockbridge, United States, 01262View on map
12.5 mi from Sheffield
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Not available
Tentrr - Running Spring Farm25 Jerusalem Road, Sandisfield, United States, 01255View on map
12.1 mi from Sheffield
Price fromUS$ 115per nightSelect
Not available
Tentrr - Echo Hill592 Rhoades And Bailey Road, New Marlborough, United States, 01259View on map
5.8 mi from Sheffield
Price fromUS$ 173per nightSelect
Not available
Berkshire Getaway Centrally Located5 Crystal Street, Lenox, United States, MA 01240View on map
16.9 mi from Sheffield
Located within a 25-minute walk to Cranwell Golf Club in Lenox, the accommodation features 2 bedrooms for up to 6 guests.
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Not available
Cozy Stockbridge Home - Walk To Golf Course!Stockbridge, Ma, 01262, Stockbridge, United States, 01262View on map
12.3 mi from Sheffield
Offering a kitchen equipped with a microwave oven, a dishwasher and a washing machine, this villa is set near Merwin House Museum.
Price fromUS$ 304per nightSelect
Not available
Waterfront Cottage - 10 Mins To Great Barrington!New Marlborough, Ma, 01230, New Marlborough, United States, 01230View on map
5.9 mi from Sheffield
Offering a kitchen complete with a microwave, a refrigerator and kitchenware, this villa is located close to Benedict Pond.
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Tranquil 3Br Stockbridge House W/Private DeckStockbridge, Ma, 01262, Stockbridge, United States, 01262View on map
13.4 mi from Sheffield
Offering a full kitchen complete with a microwave oven, a dishwasher and a refrigerator, this villa is located close to Ebenezer II Gifts and Antiques.
Price fromUS$ 316per nightSelect
Not available
3Br Lee House W/ Easy Access To Main Street!Lee, Ma, 01238, Lee, United States, 01238View on map
14.9 mi from Sheffield
Norman Rockwell Museum is 4.8 miles from this villa that offers 3 bedrooms along with a fully equipped kitchen.
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Cozy Berkshire Home, 1 Mile To Stockbridge Center!Stockbridge, MA, 01262, Stockbridge, United States, 01262View on map
12.0 mi from Sheffield
Alice's Restaurant original location is 1.1 miles from this villa that offers 4 bedrooms along with a fully equipped kitchen.
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Not available
Lakefront Berkshires House W/Deck, Dock +BoatGreat Barrington, MA, 01230, Great Barrington, United States, 01230View on map
10.4 mi from Sheffield
Offering a fully equipped kitchen complete with a microwave oven, a dishwasher and a fridge, this villa is located close to Squaw Peak.
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Rustic Berkshires Cottage, Steps To Lake Buel!, New Marlborough, United States, 01230View on map
5.9 mi from Sheffield
Taft Farms is 6 miles from this villa that offers 1 bedrooms along with a fully equipped kitchen.
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Not available
Airy Berkshires Cabin - Walk To Beach & Lake!22 Mahkeenac Road, Stockbridge, MA 01262, US, Stockbridge, United States, 01262View on map
15.1 mi from Sheffield
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Luxury Fox Hollow Home-Laurel Lake850 Summer St. M7, Lenox, United States, MA 01240View on map
15.6 mi from Sheffield
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Tentrr - Glacial Erratic At Moore Brook82 Indian Cave Road, Salisbury, United States, 06068View on map
8.7 mi from Sheffield
Price fromUS$ 169per nightSelect
Not available
Tentrr - Hillsdale Hideaway9 Primrose Drive, Hillsdale, United States, 12529View on map
10.2 mi from Sheffield
Price fromUS$ 115per nightSelect
Not available
Pet-Friendly Berkshires Home w/Dock & Fire Pit!, New Marlborough, United States, 01230View on map
5.9 mi from Sheffield
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