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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 property
  • 13 rooms in property
More Photos Photo of The Windflower Inn
From£146
Excellent 5.0 /5 Read 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
  • 2-star Rural property
  • Check in time: 3:00pm
More Photos Exterior of Quality Inn
From£79
Very good 4.0 /5 Recent 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
  • 3-star Resort property
  • 5 suites in hotel
More Photos Exterior of Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
From£86
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires : 400 Stockbridge Rd.
+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
  • Inexpensive Resort property
  • Comp. Breakfast
More Photos Image of Travelodge by Wyndham Great Barrington Berkshires
From£37
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel - 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
  • 78 rooms in property
More Photos Photo of Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
From£63
Average 3.0 /5 Recent Reviews Call BookMore Details
Blackberry River Inn : 538 Greenwoods Rd. West
+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
  • Midscale hotel
  • 17 rooms in hotel
More Photos Photo of Blackberry River Inn
From£86
Very good 4.0 /5 Review Score 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
  • 3-star Rural hotel
  • Free breakfast available
More Photos Exterior of Wake Robin Inn
From£70
Average 3.0 /5 Read Reviews Call BookMore Details
Manor House Inn - Norfolk
+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
  • Midscale Rural hotel
  • 3 floors in property
More Photos Image of Manor House Inn
From£190
Very good 4.0 /5 Guest 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
  • Affordable Rural property
  • Hotel has an eco-friendly policy See more
More Photos Exterior of The Red Lion Inn
From£181
Very good 4.0 /5 Guest 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
  • Affordable Mountain hotel
  • Hotel has a green policy See policy
More Photos Exterior of Holiday Inn Club Vacations Oak N Spruce Resort
From£70
Very good 4.0 /5 Read 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 hotel
  • 2 floors in hotel
More Photos Image of Interlaken Inn & Resort
From£165
Very good 4.0 /5 Guest Reviews 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
  • Low-priced property
  • Hotel has 28 rooms
More Photos Image of Econo Lodge Lee - Great Barrington
From£38
Average 3.0 /5 Recent 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
  • Three Star Rural hotel
  • Hotel has 6 suites
More Photos Photo of Applegate Inn
From£126
Very good 4.0 /5 Read Reviews Call BookMore Details
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Pilgrim Inn
+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 hotel
  • Check in: 3:00 PM
More Photos Exterior of Pilgrim Inn
From£63
Average 3.0 /5 Read Reviews Call BookMore Details
33 Main
+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 5-star property
More Photos hotel room
From£158
Average 3.0 /5 Review Score Call BookMore Details
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Chambery Inn - Lee
+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
  • Mid-scale property
  • 9 rooms in property
More Photos Image of Chambery Inn
From£71
Very good 4.5 /5 Hotel Reviews Call BookMore Details
Pleasant Valley Motel 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
  • Economy hotel
  • Check in: 13:00
More Photos Image of Pleasant Valley Motel West Stockbridge
From£47
Average 3.0 /5 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
  • Economical hotel
  • Check-in time: 11:00
More Photos Image of Rodeway Inn
From£47
Average 3.0 /5 Read Reviews Call BookMore Details
Quality Inn
+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
  • 3-star Lake property
  • Check-in time: 3:00 PM
More Photos Image of Quality Inn
From£51
Very good 4.0 /5 Latest 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
  • Affordable Lake hotel
  • Hotel has 2 floors
More Photos Exterior of Black Swan Inn Lee Lenox An Ascend Hotel
From£47
Very good 4.0 /5 Latest Reviews Call BookMore Details
Seven Hills Inn : 40 Plunkett St.
+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
  • Expensive Resort property
  • 2 floors in hotel
More Photos Image of Seven Hills Inn
From£146
Very good 4.5 /5 Read 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
  • Affordable property
  • 9 suites in hotel
More Photos Exterior of Wheatleigh
From£317
Very good 4.0 /5 Review Score Call BookMore Details
Canyon Ranch Lenox : 165 Kemble St.
+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
  • Three Star property
  • 102 sleeping rooms in hotel
More Photos Image of Canyon Ranch Lenox
From£71
Average 3.0 /5 Guest Reviews Call BookMore Details
Apple Tree Inn
+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 hotel
  • 6 conference rooms in property
More Photos Exterior of Apple Tree Inn
From£79
Average 3.0 /5 Guest Reviews 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
  • High end Rural hotel
  • Free breakfast
More Photos Exterior of Brook Farm Inn
From£95
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Kemble Inn
+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
  • Three Star Mountain hotel
  • 12 rooms in hotel
More Photos Exterior of Kemble Inn
From£210
Very good 4.0 /5 Read Reviews Call BookMore Details
The Constance by The Lenox Collection - Lenox
+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
  • 4 star property
  • 24 rooms in property
More Photos Exterior of The Constance by The Lenox Collection
From£178
Average 3.0 /5 Recent Reviews 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
  • Affordable property
  • 30 rooms in property
More Photos hotel room
From£158
Average 3.0 /5 Recent 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 property
  • Free comp. breakfast
More Photos hotel room
From£59
Average 3.0 /5 Read Reviews Call BookMore Details
The Cornell Inn, Lenox - 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
  • Complimentary breakfast is offered
More Photos Image of The Cornell Inn, Lenox
From£47
Very good 4.0 /5 Hotel 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
  • 2 floors in hotel
More Photos Exterior of Eastover Estate & Retreat
From£86
Average 3.5 /5 Guest Reviews Call BookMore Details
Life House Berkshires : 194 Pittsfield Rd.
+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 property
  • Free breakfast
More Photos Exterior of Life House Berkshires
From£38
Average 3.0 /5 Latest Reviews Call BookMore Details
Howard Johnson by Wyndham 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
  • Low Cost Resort hotel
  • Hotel has 44 rooms
More Photos Image of Howard Johnson by Wyndham Lenox
From£51
Average 3.0 /5 Hotel 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
  • Four star Resort property
  • Hotel has an eco-friendly policy Read more
More Photos Photo of Miraval Berkshires Resort & Spa - All Inclusive Adults Only
From£109
Average 3.0 /5 Review Score Call BookMore Details
The Amselhaus - 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
  • Four-star Riverfront property
  • Comp. Breakfast
More Photos hotel room
From£198
Very good 4.0 /5 Hotel 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
  • 3 conference rooms in property
More Photos hotel room
From£119
Very good 4.5 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox in 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
  • Free comp. breakfast
More Photos Image of Hampton Inn & Suites Berkshires-Lenox
From£86
Average 3.0 /5 Latest Reviews Call BookMore Details
Yankee Inn
+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
  • Inexpensive hotel
  • 9 suites in hotel
More Photos Image of Yankee Inn
From£115
Very good 4.0 /5 Read Reviews 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
  • Economy Downtown hotel
  • 16 rooms in property
More Photos Photo of Knights Inn Lenox
From£29
Poor 2.0 /5 Read Reviews Call BookMore Details
Lenox Inn - Lenox
+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 hotel
More Photos Photo of Lenox Inn
From£47
Poor 2.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Lenox Pittsfield in 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 property
  • 4 floors in property
More Photos Photo of Hilton Garden Inn Lenox Pittsfield
From£75
Very good 4.0 /5 Hotel Reviews 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 hotel
  • Gym is available on property
More Photos Exterior of Best Western Plus Berkshire Hills Inn & Suites
From£62
Very good 4.0 /5 Guest 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
  • Low-priced Suburban property
  • Check in time: 3:00pm
More Photos Image of Americas Best Value Inn Torrington CT
From£45
Poor 2.0 /5 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 Image of Berkshire Inn
From£71
Average 3.0 /5 Latest Reviews Call BookMore Details
St. Charles Hotel - Hudson
+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
  • 2 star Downtown property
  • 34 rooms in property
More Photos Exterior of St. Charles Hotel
From£63
Average 3.0 /5 Review Score 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
  • 3 star Downtown property
  • 170 sleeping rooms in hotel
More Photos Photo of Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
From£63
Average 3.0 /5 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
  • Affordable Downtown property
  • 3 floors in property
More Photos hotel room
From£59
Very good 4.0 /5 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
  • 6 suites in hotel
More Photos Photo of Hotel on North
From£119
Excellent 5.0 /5 Hotel Reviews Call BookMore Details
The Nest Hudson Hotel : 330 Union St.
+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
  • Four star Downtown property
  • Hotel has 6 rooms
More Photos Photo of The Nest Hudson Hotel
From£158
Very good 4.5 /5 Latest 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
  • Inexpensive Mountain hotel
  • Free comp. breakfast
More Photos Photo of Days Inn by Wyndham Torrington
From£47
Average 3.0 /5 Guest 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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