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Sheffield Massachusetts Accommodations

Find hotels & motels in Sheffield using the list below. Explore our guide for inexpensive and discount hotel/motel rates in or near Sheffield, MA for your upcoming personal or group travel. We list the best Sheffield Massachusetts hotel rooms. Review the Sheffield hotel list below to find the perfect lodging. We also have a map of the Sheffield hotels.

The Sheffield center point is approximately 8 miles west of Monument Mountain Reservation and 11 miles northwest of Tobey Pond.

Sheffield Hotels/Accommodations

The Windflower Inn in Great Barrington
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
684 South Egremont Rd., Great Barrington, MA 01230 ~4.60 miles northwest of Sheffield
  • Midscale Mountain property
  • Check in: 2:00PM
More Photos Exterior of The Windflower Inn
From£147
Excellent 5.0 /5 Hotel Reviews Call BookMore Details
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Quality Inn - Great Barrington
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
372 Main St., Great Barrington, MA 01230 Website ~5.62 miles north of Sheffield
  • Two-star Rural property
  • Check in: 3:00pm
More Photos Photo of Quality Inn
From£79
Very good 4.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi in Great Barrington
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
249 Stockbridge Rd., Great Barrington, MA 01230 Website ~6.70 miles north of Sheffield
  • Mid-scale Resort property
  • 60 sleeping rooms in hotel
More Photos Photo of Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
From£86
Very good 4.0 /5 Guest Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
400 Stockbridge Rd., Great Barrington, MA 01230 ~7.04 miles north of Sheffield
  • Two-star Resort property
  • Free breakfast available
More Photos Photo of Travelodge by Wyndham Great Barrington Berkshires
From£37
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel : 415 Stockbridge Road41
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
415 Stockbridge Road41, Great Barrington, MA 01230 ~7.10 miles north of Sheffield
  • Mid-scale Mountain property
  • Hotel has an eco-friendly policy Read more
More Photos Photo of Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
From£63
Average 3.0 /5 Guest Reviews Call BookMore Details
Blackberry River Inn
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
538 Greenwoods Rd. West, Norfolk, CT 06058 ~9.32 miles southeast of Sheffield
  • Affordable hotel
  • 17 sleeping rooms in hotel
More Photos Exterior of Blackberry River Inn
From£86
Very good 4.0 /5 Read Reviews Call BookMore Details
Wake Robin Inn : 106 Sharon Rd.
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
106 Sharon Rd., Lakeville, CT 06039 ~11.32 miles southwest of Sheffield
  • Three Star Rural property
  • Check in time: 3 pm
More Photos Exterior of Wake Robin Inn
From£70
Average 3.0 /5 Recent Reviews Call BookMore Details
Manor House Inn : 69 Maple Ave.
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
69 Maple Ave., Norfolk, CT 06058 ~11.57 miles southeast of Sheffield
  • Three Star Rural property
  • Has environment-friendly policy Read more
More Photos Photo of Manor House Inn
From£190
Very good 4.0 /5 Review Score Call BookMore Details
The Red Lion Inn - Stockbridge
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
30 Main St., Stockbridge, MA 01262 ~12.02 miles north of Sheffield
  • Mid-scale Rural property
  • Check in: 3:00
More Photos Exterior of The Red Lion Inn
From£63
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort - South Lee
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
190 Meadow St., South Lee, MA 01260 ~12.06 miles north of Sheffield
  • Mid-scale Mountain hotel
  • 334 suites in property
More Photos Photo of Holiday Inn Club Vacations Oak N Spruce Resort
From£70
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Interlaken Inn & Resort
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
74 Interlaken Rd., Lakeville, CT 06039 ~12.19 miles southwest of Sheffield
  • Three Star Resort property
  • Hotel has 2 floors
More Photos Image of Interlaken Inn & Resort
From£166
Very good 4.0 /5 Review Score Call BookMore Details
Econo Lodge Lee - Great Barrington
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
980 Pleasant St., Lee, MA 01238 ~12.58 miles northeast of Sheffield
  • 2-star hotel
  • Free breakfast
More Photos Exterior of Econo Lodge Lee - Great Barrington
From£38
Average 3.0 /5 Guest Reviews Call BookMore Details
Applegate Inn
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
279 West Park St., Lee, MA 01238 ~14.31 miles northeast of Sheffield
  • 3-star Rural hotel
  • 3 floors in property
More Photos Exterior of Applegate Inn
From£127
Very good 4.0 /5 Reviews Call BookMore Details
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Pilgrim Inn - Lee
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
165 Housatonic St., Lee, MA 01238 ~14.37 miles northeast of Sheffield
  • 3 star property
More Photos Exterior of Pilgrim Inn
From£63
Average 3.0 /5 Reviews Call BookMore Details
33 Main : 33 Main St.
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
33 Main St., Lenox, MA 01238 ~14.49 miles northeast of Sheffield
  • Luxurious Five Star property
More Photos hotel room
From£159
Average 3.0 /5 Read Reviews Call BookMore Details
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Chambery Inn
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
199 Main St., Lee, 01238 ~14.69 miles north of Sheffield
  • 3 star hotel
  • Hotel has 9 rooms
More Photos Photo of Chambery Inn
From£71
Very good 4.5 /5 Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge in West Stockbridge
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
42 Stockbridge Rd., West Stockbridge, MA 01266 ~14.83 miles north of Sheffield
  • Economical hotel
  • 16 sleeping rooms in hotel
More Photos Photo of Pleasant Valley Motel West Stockbridge
From£47
Average 3.0 /5 Read Reviews Call BookMore Details
Rodeway Inn - Lee
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
200 Laurel St., Lee, MA 01238 ~15.07 miles north of Sheffield
  • Two-star property
More Photos Image of Rodeway Inn
From£47
Average 3.0 /5 Read Reviews Call BookMore Details
Quality Inn - Lee
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
435 Laurel St., Lee, MA 01238 ~15.35 miles north of Sheffield
  • Midscale Lake property
  • Check-in: 3:00 PM
More Photos Exterior of Quality Inn
From£51
Very good 4.0 /5 Reviews Call BookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel : 435 Laurel St.
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
435 Laurel St., Lee, MA 01238 ~15.36 miles north of Sheffield
  • 3 star Lake hotel
  • Check-in: 3:00PM
More Photos Photo of Black Swan Inn Lee Lenox An Ascend Hotel
From£47
Very good 4.0 /5 Guest Reviews Call BookMore Details
Seven Hills Inn
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
40 Plunkett St., Lenox, MA 01240 ~16.00 miles north of Sheffield
  • 4 star Resort hotel
  • Hotel has an eco-friendly policy See more
More Photos Exterior of Seven Hills Inn
From£146
Very good 4.5 /5 Recent Reviews Call BookMore Details
Wheatleigh
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
Hawthorne Rd., Lenox, MA 01240 ~16.37 miles north of Sheffield
  • Three Star property
  • Check in: 16:00
More Photos Exterior of Wheatleigh
From£318
Very good 4.0 /5 Recent Reviews Call BookMore Details
Canyon Ranch Lenox
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
165 Kemble St., Lenox, MA 01240 ~16.61 miles north of Sheffield
  • Mid-scale property
  • Hotel has 2 floors
More Photos Image of Canyon Ranch Lenox
From£71
Average 3.0 /5 Recent Reviews Call BookMore Details
Apple Tree Inn in Lenox
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
10 Richmond Mountain Rd., Lenox, MA 01240 ~16.91 miles north of Sheffield
  • 4 star Mountain property
  • 3 floors in property
More Photos Image of Apple Tree Inn
From£79
Average 3.0 /5 Hotel Reviews Call BookMore Details
Brook Farm Inn
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
15 Hawthorne St., Lenox, MA 01240 ~17.06 miles north of Sheffield
  • 4-star Rural hotel
  • Hotel has an eco-friendly policy See policy
More Photos Image of Brook Farm Inn
From£95
Very good 4.0 /5 Recent Reviews Call BookMore Details
Kemble Inn : 2 Kemble St.
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
2 Kemble St., Lenox, MA 01240 ~17.26 miles north of Sheffield
  • Midscale Mountain hotel
  • 3 floors in property
More Photos Exterior of Kemble Inn
From£210
Very good 4.0 /5 Hotel Reviews Call BookMore Details
The Constance by The Lenox Collection : 11 Old Stockbridge Rd.
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
11 Old Stockbridge Rd., Lenox, MA 01240 ~17.31 miles north of Sheffield
  • High-end property
  • 24 rooms in property
More Photos Image of The Constance by The Lenox Collection
From£179
Average 3.0 /5 Review Score Call BookMore Details
The Whitlock by The Lenox Collection : 16 Church St.
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
16 Church St., Lenox, MA 01240 ~17.38 miles north of Sheffield
  • Midscale hotel
  • 2 floors in property
More Photos hotel room
From£159
Average 3.0 /5 Reviews Call BookMore Details
The Dewey by The Lenox Collection
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
7 Hubbard St., Lenox, MA 01240 ~17.83 miles north of Sheffield
  • High end hotel
  • 2 floors in property
More Photos hotel room
From£59
Average 3.0 /5 Guest Reviews Call BookMore Details
The Cornell Inn, Lenox in Lenox
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
203 Main St., Lenox, MA 01240 ~18.06 miles north of Sheffield
  • Affordable Mountain hotel
  • 28 rooms in property
More Photos Photo of The Cornell Inn, Lenox
From£47
Very good 4.0 /5 Read Reviews Call BookMore Details
Eastover Estate & Retreat in Lenox
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
430 East St., Lenox, MA 01240 ~18.62 miles north of Sheffield
  • 4-star Mountain property
  • Hotel has 90 rooms
More Photos Image of Eastover Estate & Retreat
From£86
Average 3.5 /5 Latest Reviews Call BookMore Details
Life House Berkshires
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
194 Pittsfield Rd., Lenox, MA 01240 ~19.49 miles north of Sheffield
  • Low priced Suburban property
  • Free breakfast available
More Photos Exterior of Life House Berkshires
From£38
Average 3.0 /5 Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox in Lenox
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
462 Pittsfield Rd., Lenox, MA 01240 ~19.70 miles north of Sheffield
  • Cheap Resort hotel
  • Check-in: 2:00 PM
More Photos Photo of Howard Johnson by Wyndham Lenox
From£51
Average 3.0 /5 Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only in Lenox
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
55 Lee Rd., Lenox, MA 01240 ~20.22 miles north of Sheffield
  • 4-star Resort hotel
  • 105 rooms in property
More Photos Exterior of Miraval Berkshires Resort & Spa - All Inclusive Adults Only
From£109
Average 3.0 /5 Guest Reviews Call BookMore Details
The Amselhaus in Cornwall Bridge
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
6 Rug Rd., Cornwall Bridge, CT 06754 ~20.24 miles south of Sheffield
  • High-end Riverfront hotel
  • Check-in: 0:00 pm
More Photos hotel room
From£198
Very good 4.0 /5 Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center : 802 State Rd.
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
802 State Rd., Richmond, MA 01254 ~20.48 miles north of Sheffield
  • Midscale Rural property
  • 3 conference rooms in property
More Photos hotel room
From£119
Very good 4.5 /5 Review Score Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
445 Pittsfield Rd., Lenox, MA 01240 ~20.67 miles north of Sheffield
  • Affordable Mountain property
  • 79 rooms in hotel
More Photos Image of Hampton Inn & Suites Berkshires-Lenox
From£86
Average 3.0 /5 Recent Reviews Call BookMore Details
Yankee Inn in Lenox
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
461 Pittsfield Rd., Lenox, MA 01240 ~20.72 miles north of Sheffield
  • Economy hotel
  • 3 floors in property
More Photos Exterior of Yankee Inn
From£115
Very good 4.0 /5 Review Score Call BookMore Details
Knights Inn Lenox : 474 Pittsfield Rd.
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
474 Pittsfield Rd., Lenox, MA 01240 ~20.75 miles north of Sheffield
  • Two star Downtown property
  • 16 sleeping rooms in hotel
More Photos Photo of Knights Inn Lenox
From£29
Poor 2.0 /5 Recent Reviews Call BookMore Details
Lenox Inn
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
525 Pittsfield Rd., Lenox, MA 01240 ~20.99 miles north of Sheffield
  • Cheap hotel
  • Check-in: 15:00
More Photos Image of Lenox Inn
From£47
Poor 2.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
1032 South St., Pittsfield, MA 01201 ~21.05 miles north of Sheffield
  • 3-star Suburban hotel
  • 2 meeting rooms in hotel
More Photos Photo of Hilton Garden Inn Lenox Pittsfield
From£75
Very good 4.0 /5 Read Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites : 1350 West Housatonic St.
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1350 West Housatonic St., Pittsfield, MA 01201 ~22.47 miles north of Sheffield
  • Mid-scale Rural hotel
  • Gym / Fitness Center Available
More Photos Photo of Best Western Plus Berkshire Hills Inn & Suites
From£62
Very good 4.0 /5 Review Score Call BookMore Details
Americas Best Value Inn Torrington CT : 395 Winsted Rd.
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
395 Winsted Rd., Torrington, CT 06790 ~23.33 miles southeast of Sheffield
  • Economy Suburban hotel
  • Check-in: 3:00pm
More Photos Image of Americas Best Value Inn Torrington CT
From£45
Poor 2.0 /5 Guest Reviews Call BookMore Details
Berkshire Inn : 150 West Housatonic St.
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
150 West Housatonic St., Pittsfield, MA 01201 ~23.52 miles north of Sheffield
  • Two star Downtown hotel
  • Hotel has 2 floors
More Photos Exterior of Berkshire Inn
From£71
Average 3.0 /5 Read Reviews Call BookMore Details
St. Charles Hotel
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
16 Park Place, Hudson, NY 12534 ~23.78 miles west of Sheffield
  • Economy Downtown hotel
  • Hotel has 34 rooms
More Photos Exterior of St. Charles Hotel
From£63
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel in Pittsfield
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
1 West St., Pittsfield, MA 01201 ~23.89 miles north of Sheffield
  • 3 star Downtown hotel
  • 14 floors in hotel
More Photos Image of Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
From£63
Average 3.0 /5 Recent Reviews Call BookMore Details
Hudson Whaler
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
542 Warren St., Hudson, NY 12534 ~23.93 miles west of Sheffield
  • Mid-scale Downtown property
  • Hotel has 16 rooms
More Photos hotel room
From£59
Very good 4.0 /5 Latest Reviews Call BookMore Details
Hotel on North - Pittsfield
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
297 North St., Pittsfield, MA 01201 ~24.21 miles north of Sheffield
  • 4-star Downtown property
  • 6 suites in hotel
More Photos Image of Hotel on North
From£119
Excellent 5.0 /5 Hotel Reviews Call BookMore Details
The Nest Hudson Hotel in Hudson
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
330 Union St., Hudson, NY 12534 ~24.29 miles west of Sheffield
  • High end Downtown property
  • 3 floors in hotel
More Photos Photo of The Nest Hudson Hotel
From£159
Very good 4.5 /5 Reviews Call BookMore Details
Days Inn by Wyndham Torrington in Torrington
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
492 East Main St., Torrington, CT 06790 ~24.50 miles southeast of Sheffield
  • Cheap Mountain property
  • Free comp. breakfast
More Photos Image of Days Inn by Wyndham Torrington
From£47
Average 3.0 /5 Hotel Reviews Call BookMore Details

Next: See My Sheffield Hotels with Pricing

Graph: Upcoming 20 Days of Sheffield Hotel Rates

Rates shown are nightly rates before taxes and do not necessarily reflect all Sheffield, MA discounts available. The chart reflects the cheapest Sheffield hotel for each day and each star rating category.

FAQs about hotels in Sheffield

What are the most favored hotels in Sheffield?

The Windflower Inn, Hotel on North and Chambery Inn are the best rated hotels based on customer reviews in the last 365 days.

What are the most high-end hotels in Sheffield?

33 Main, Seven Hills Inn and Apple Tree Inn are the top 3 luxury hotels near Sheffield city center.

What hotels are closest to the city center of Sheffield?

The Windflower Inn, Quality Inn, and Fairfield Inn & Suites by Marriott Great Barrington Lenox are the properties closest to Sheffield city center.

What are the best independent hotels in Sheffield?

The Windflower Inn, Hotel on North and Chambery Inn are the best rated independent hotels (not part of a big brand).

What are the most popular Choice Hotels branded hotels in Sheffield?

Quality Inn, Quality Inn and Black Swan Inn Lee Lenox An Ascend Hotel are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the most popular IHG hotels in Sheffield?

Holiday Inn Club Vacations Oak N Spruce Resort, Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel and Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel are the best rated Intercontinental Hotel Group (IHG) branded hotels (based on user reviews score).

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