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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
  • 3-star Mountain hotel
  • 2 conference rooms in property
More Photos Exterior of The Windflower Inn
From£147
Excellent 5.0 /5 Guest Reviews Call BookMore Details
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Quality Inn
+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
  • Low-priced Rural property
  • Check in: 3:00pm
More Photos Photo of Quality Inn
From£79
Very good 4.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
+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
  • Affordable Resort property
  • Comp. Breakfast
More Photos Image of Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
From£86
Very good 4.0 /5 Review Score Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires in Great Barrington
+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
  • 2 star Resort property
  • Free complimentary breakfast
More Photos Image of Travelodge by Wyndham Great Barrington Berkshires
From£37
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel in Great Barrington
+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
  • 3-star Mountain property
  • 6 suites in property
More Photos Exterior of Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
From£63
Average 3.0 /5 Read 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
  • Three Star hotel
  • 2 floors in property
More Photos Exterior of Blackberry River Inn
From£86
Very good 4.0 /5 Reviews Call BookMore Details
Wake Robin Inn
+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
  • Mid-scale Rural hotel
  • Hotel has 3 meeting rooms
More Photos Photo of Wake Robin Inn
From£70
Average 3.0 /5 Guest Reviews Call BookMore Details
Manor House Inn
+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
  • 3-star Rural property
  • Hotel has 7 suites
More Photos Exterior of Manor House Inn
From£191
Very good 4.0 /5 Hotel Reviews 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 ~12.05 miles north of Sheffield
  • Midscale Rural property
  • Hotel has 8 meeting rooms
More Photos Image of The Red Lion Inn
From£182
Very good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort
+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 property
  • 334 suites in hotel
More Photos Image of Holiday Inn Club Vacations Oak N Spruce Resort
From£70
Very good 4.0 /5 Recent 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
  • Affordable Resort property
  • Gym / Fitness Center Available
More Photos Photo of Interlaken Inn & Resort
From£166
Very good 4.0 /5 Read Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington in Lee
+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 property
  • Free complimentary breakfast
More Photos Image of Econo Lodge Lee - Great Barrington
From£38
Average 3.0 /5 Reviews Call BookMore Details
Applegate Inn in Lee
+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
  • Affordable Rural property
  • Check-in time: 2 pm
More Photos Image of Applegate Inn
From£127
Very good 4.0 /5 Recent Reviews Call BookMore Details
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Quality Inn
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
170 Housatonic St., Lee, MA 01238 ~14.35 miles northeast of Sheffield
  • 2-star property
  • Check-in: 11:00 AM
More Photos Photo of Quality Inn
From£37
Average 3.0 /5 Latest Reviews Call BookMore Details
Pilgrim Inn : 165 Housatonic St.
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
165 Housatonic St., Lee, MA 01238 ~14.37 miles northeast of Sheffield
  • 3-star property
  • Check in: 3:00 PM
More Photos Image of Pilgrim Inn
From£63
Average 3.0 /5 Hotel Reviews Call BookMore Details
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33 Main - Lenox
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 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 Review Score Call BookMore Details
Chambery Inn : 199 Main St.
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
199 Main St., Lee, 01238 ~14.69 miles north of Sheffield
  • Affordable property
  • Check in: 14:00
More Photos Exterior of Chambery Inn
From£71
Very good 4.5 /5 Recent Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge - West Stockbridge
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
42 Stockbridge Rd., West Stockbridge, MA 01266 ~14.83 miles north of Sheffield
  • Economical hotel
More Photos Image of Pleasant Valley Motel West Stockbridge
From£47
Average 3.0 /5 Latest Reviews Call BookMore Details
Rodeway Inn
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 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 Latest Reviews Call BookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel
+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
  • Mid-scale 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 Latest 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
  • Four-star Resort property
  • 57 sleeping rooms in hotel
More Photos Exterior of Seven Hills Inn
From£146
Very good 4.5 /5 Guest Reviews Call BookMore Details
Wheatleigh : Hawthorne Rd.
+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
  • 3-star hotel
  • Free comp. breakfast
More Photos Exterior of Wheatleigh
From£318
Very good 4.0 /5 Latest Reviews Call BookMore Details
Canyon Ranch Lenox in 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
  • 3-star hotel
  • Shuttle to airport available
More Photos Image of Canyon Ranch Lenox
From£71
Average 3.0 /5 Latest Reviews Call BookMore Details
Apple Tree Inn : 10 Richmond Mountain Rd.
+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
  • Four star Mountain property
  • Hotel has 34 rooms
More Photos Photo of Apple Tree Inn
From£79
Average 3.0 /5 Review Score Call BookMore Details
Brook Farm Inn : 15 Hawthorne St.
+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
  • Four star Rural hotel
  • Free complimentary breakfast
More Photos Photo of Brook Farm Inn
From£95
Very good 4.0 /5 Read 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
  • Mid-scale Mountain property
  • 12 suites in property
More Photos Exterior of Kemble Inn
From£210
Very good 4.0 /5 Latest Reviews Call BookMore Details
The Constance
+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
More Photos Photo of The Constance
From£179
Average 3.0 /5 Guest Reviews Call BookMore Details
The Whitlock in Lenox
+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
  • Affordable hotel
  • Hotel has 32 rooms
More Photos hotel room
From£159
Average 3.0 /5 Review Score Call BookMore Details
The Dewey
+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
  • 4-star hotel
More Photos hotel room
From£59
Average 3.0 /5 Recent 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
  • 3 star Mountain hotel
  • Check-in: 3:00 PM-8PM
More Photos Exterior of The Cornell Inn, Lenox
From£47
Very good 4.0 /5 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
  • Four-star Mountain hotel
  • 2 floors in hotel
More Photos Image of Eastover Estate & Retreat
From£86
Average 3.5 /5 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
  • 2-star Suburban hotel
  • Free breakfast available
More Photos Photo of Life House Berkshires
From£39
Average 3.0 /5 Latest Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox - 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 property
  • Complimentary breakfast is offered
More Photos Photo of Howard Johnson by Wyndham Lenox
From£51
Average 3.0 /5 Guest Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only - 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
  • High end Resort hotel
  • Fitness + Health Center
More Photos Photo of Miraval Berkshires Resort & Spa - All Inclusive Adults Only
From£109
Average 3.0 /5 Read 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 Recent Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center in Richmond
+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
  • Check in: 3:00 p.m.
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
  • Midscale Mountain hotel
  • Check in time: 3:00 pm
More Photos Image of Hampton Inn & Suites Berkshires-Lenox
From£86
Average 3.0 /5 Recent Reviews Call BookMore Details
The Yankee, Trademark Collection by Wyndham - 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
  • Low priced property
  • 9 suites in property
More Photos Exterior of The Yankee, Trademark Collection by Wyndham
From£51
Very good 4.0 /5 Reviews Call BookMore Details
Knights Inn Lenox
+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
  • Cheap Downtown hotel
  • Check-in time: 2.00 pm
More Photos Photo of Knights Inn Lenox
From£29
Poor 2.0 /5 Guest 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
  • Economical property
More Photos Image of Lenox Inn
From£47
Poor 2.0 /5 Review Score 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
  • Mid-scale Suburban hotel
  • Access to gym on-site
More Photos Exterior of Hilton Garden Inn Lenox Pittsfield
From£75
Very good 4.0 /5 Review Score Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites
+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
  • Midscale Rural property
  • 3 floors in property
More Photos Image of Best Western Plus Berkshire Hills Inn & Suites
From£62
Very good 4.0 /5 Reviews Call BookMore Details
Americas Best Value Inn Torrington CT
+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
  • Inexpensive Suburban hotel
  • Check in time: 3:00pm
More Photos Photo of Americas Best Value Inn Torrington CT
From£45
Poor 2.0 /5 Recent Reviews Call BookMore Details
Berkshire Inn in Pittsfield
+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 Image of Berkshire Inn
From£71
Average 3.0 /5 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
  • Low-priced Downtown hotel
  • Hotel has 6 suites
More Photos Image of St. Charles Hotel
From£63
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
+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
  • Affordable Downtown hotel
  • Hotel has 170 rooms
More Photos Exterior of Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
From£63
Average 3.0 /5 Recent Reviews Call BookMore Details
Hudson Whaler in Hudson
+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
  • Affordable Downtown property
  • 16 rooms in property
More Photos hotel room
From£59
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hotel on North : 297 North St.
+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
  • Four-star Downtown property
  • 45 sleeping rooms in hotel
More Photos Image of Hotel on North
From£119
Excellent 5.0 /5 Latest Reviews Call BookMore Details
The Nest Hudson Hotel
+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
  • Hotel has 6 suites
More Photos Image of The Nest Hudson Hotel
From£159
Very good 4.5 /5 Guest Reviews Call BookMore Details
Days Inn by Wyndham 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
  • Two-star Mountain property
  • Check in time: 11:00 AM
More Photos Photo of Days Inn by Wyndham Torrington
From£47
Average 3.0 /5 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 best Marriott hotels in Sheffield?

Fairfield Inn & Suites by Marriott Great Barrington Lenox and The Yankee, Trademark Collection by Wyndham are the best rated Marriott/Starwood branded hotels (based on customer reviews score).

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

Quality Inn, Black Swan Inn Lee Lenox An Ascend Hotel and Econo Lodge Lee - Great Barrington 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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