Find hotels in Sheffield, MA from ₩106,540
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Aug 30 - Aug 31Tomorrow
Aug 31 - Sep 1Next weekend
Sep 4 - Sep 6In two weeks
Sep 11 - Sep 13Our top choices for Sheffield hotels
1. Wilder House Berkshires
Wilder House BerkshiresSheffield
Jennifer
₩270,768
₩302,448 total
includes taxes & fees
Sep 1 - Sep 2
2. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
BJORN
₩158,279
₩176,805 total
includes taxes & fees
Sep 7 - Sep 8
3. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
Lisa
₩221,109
₩246,979 total
includes taxes & fees
Sep 7 - Sep 8
4. Monument Mountain Motel
Monument Mountain MotelGreat Barrington
Charlie
₩117,677
₩131,440 total
includes taxes & fees
Sep 1 - Sep 2
5. Quality Inn Great Barrington
Quality Inn Great BarringtonGreat Barrington
Sisile
₩127,518
₩142,437 total
includes taxes & fees
Sep 20 - Sep 21
6. Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington BerkshiresGreat Barrington
Elspeth
₩108,731
₩121,453 total
includes taxes & fees
Sep 1 - Sep 2
7. Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLCEast Canaan
Regina
₩144,516
₩166,193 total
includes taxes & fees
Sep 2 - Sep 3
8. Little Cat Lodge
Little Cat LodgeCopake Falls
Kees
₩246,503
₩276,083 total
includes taxes & fees
Sep 1 - Sep 2
9. Blackberry River Inn
Blackberry River InnNorfolk
Rachel
₩261,505
₩300,731 total
includes taxes & fees
Sep 1 - Sep 2
10. The Yankee Inn
The Yankee InnLenox
Karen
₩143,139
₩159,886 total
includes taxes & fees
Sep 17 - Sep 18
11. the Alander
the AlanderCopake
Phil
₩233,978
₩262,055 total
includes taxes & fees
Sep 1 - Sep 2
12. The Little Lion
The Little LionGreat Barrington
Anne
₩154,838
₩172,951 total
includes taxes & fees
Sep 1 - Sep 2
13. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
James
₩175,483
₩196,014 total
includes taxes & fees
Sep 21 - Sep 22
14. East Rock Inn
East Rock InnGreat Barrington
ERIK
₩203,561
₩227,377 total
includes taxes & fees
Sep 22 - Sep 23
15. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
Christine
₩150,916
₩168,573 total
includes taxes & fees
Sep 20 - Sep 21
16. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
Robert
₩110,647
₩154,340 total
includes taxes & fees
Oct 1 - Oct 2
17. Gedney Farm
Gedney FarmGreat Barrington
Jane
₩315,870
₩346,509 total
includes taxes & fees
Sep 1 - Sep 2
18. Interlaken Inn & Resort
Interlaken Inn & ResortLakeville
Stacie
₩296,050
₩340,457 total
includes taxes & fees
Sep 22 - Sep 23
19. Berkshire Travel Lodge
Berkshire Travel LodgeAusterlitz
Kris
₩92,889
₩104,037 total
includes taxes & fees
Sep 1 - Sep 2
20. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
Sheila
₩108,731
₩121,453 total
includes taxes & fees
Sep 1 - Sep 2
Stay near popular Sheffield attractions
Ashley House
Built in 1735, the Ashley House is where Elizabeth Freeman successfully sued for her freedom, helping end slavery in Massachusetts. Tour the historic rooms and learn about this pivotal chapter in American history.
Thom Reed UFO Monument Park
8.0/10 (1 review)
America's first officially documented UFO encounter is commemorated at this riverside park in Sheffield. Explore plaques about the Reed family's 1969 experience while enjoying Housatonic River views.
Bartholomews Cobble
Twin rocky knolls form this National Natural Landmark, home to one of North America's most diverse fern collections. Explore five miles of trails through forests and riverbanks for exceptional wildlife viewing.
Drury Preserve
Explore diverse ecosystems along a serene 2.4-mile trail through hemlock forests and calcareous wetlands. Cross wooden boardwalks to a tranquil pond where great blue herons and other wildlife await.
Lime Kiln Farm Wildlife Sanctuary
This wildlife sanctuary showcases diverse plant species across limestone ridges and conifer forests. Explore trails to spot numerous butterfly species and Pileated Woodpeckers in the tranquil Berkshires landscape.
Bartholomew's Cobble
10.0/10 (1 review)
This National Natural Landmark features twin rocky knolls and North America's most diverse fern collection. Explore its trails through varied ecosystems while watching for peregrine falcons and rare plants.
Learn more about Sheffield
Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.
See all hotels in Sheffield
Top Sheffield Hotel Reviews
Quality Inn Lee - Lenox South
10/10 Excellent
"The hotel was very clean and well maintained. The lobby and stairs were very clean and looked as though everything was painted recently. The room was very clean and modern and bed was comfortable. The bathroom was also clean. We only stayed the one night for a concert at Tanglewood so we didn’t use any of the amenities or have the free breakfast. But if they were anything like the rest of the hotel, I’m sure they were above average. Would definitely stay again when in the area."
Holiday Inn Club Vacations Oak 'n Spruce Resort
10/10 Excellent
"Great for families"
Holiday Inn Express Hotel & Suites Great Barrington by IHG
10/10 Excellent
"This facility appeared to be brand new. Breakfast was excellent and the dining area was spacious and attractive. We would definitely recommend this hotel and will stay here again when we are back in the area!"
Berkshire Mountain Lodge
10/10 Excellent
"Good experience"
Little Cat Lodge
10/10 Excellent
"Beautifully decorated and comfortable with great continental breastfast and stunning mountain views."
Berkshires Untold
10/10 Excellent
"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."
The Red Lion Inn
10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Hampton Inn & Suites Berkshires-Lenox
10/10 Excellent
"We were there for one night and it worked out great. Nice breakfast!"
Prospect Berkshires
10/10 Excellent
"It was beautiful but quite expensive. There was no housekeeping included so trash was not picked up and the breakfasts were grossly overpriced!"
More cheap stays in Sheffield
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
₩108,731
₩121,453 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (906 reviews)
Quality Inn Great Barrington
372 Main Street Great Barrington MA
₩127,518
₩142,437 total
Sep 20 - Sep 21
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
The Yankee Inn
461 Pittsfield Rd Lenox MA
₩143,139
₩159,886 total
Sep 17 - Sep 18
includes taxes & fees
Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
₩150,916
₩168,573 total
Sep 20 - Sep 21
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
₩162,408
₩181,415 total
Sep 8 - Sep 9
includes taxes & fees
Hideaway Inn Lenox
11 Old Stockbridge Rd Lenox MA
₩191,724
₩214,158 total
Sep 7 - Sep 8
includes taxes & fees
