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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, Motels & Accommodations

The Windflower Inn : 684 South Egremont Rd.
+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 ~4.59 miles northwest of Sheffield
  • Mid-scale Mountain property
  • 2 meeting rooms in property
More Photos Image of The Windflower Inn
From£137
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 ~5.61 miles north of Sheffield
  • Cheap Rural property
  • Check in: 3:00pm
More Photos Exterior of Quality Inn
From£74
Very good 4.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi : 249 Stockbridge Rd.
+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 ~6.69 miles north of Sheffield
  • Mid-scale Resort property
  • 3 floors in hotel
More Photos Image of Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
From£80
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires - 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 ~7.03 miles north of Sheffield
  • Low Cost Resort hotel
More Photos Exterior of Travelodge by Wyndham Great Barrington Berkshires
From£34
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express Great Barrington 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 Rd., Great Barrington, MA 01230 ~7.13 miles north of Sheffield
  • Midscale Mountain property
  • Hotel has 6 suites
More Photos Exterior of Holiday Inn Express Great Barrington
From£66
Very good 4.0 /5 Hotel 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 ~9.30 miles southeast of Sheffield
  • 3-star property
  • 2 floors in property
More Photos Image of Blackberry River Inn
From£80
Very good 4.0 /5 Read 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 ~11.30 miles southwest of Sheffield
  • Three Star Rural hotel
  • Free breakfast
More Photos Exterior of Wake Robin Inn
From£66
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 ~11.55 miles southeast of Sheffield
  • Affordable Rural property
  • Comp. Breakfast
More Photos Exterior of Manor House Inn
From£178
Very good 4.0 /5 Latest Reviews Call BookMore Details
The Red Lion Inn
+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 ~12.00 miles north of Sheffield
  • 3-star Rural property
  • Hotel has 125 rooms
More Photos Exterior of The Red Lion Inn
From£59
Average 3.0 /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 ~12.04 miles north of Sheffield
  • Three Star Mountain property
  • Hotel has 334 suites
More Photos Exterior of Holiday Inn Club Vacations Oak N Spruce Resort
From£66
Very good 4.0 /5 Latest Reviews Call BookMore Details
Interlaken Inn in Lakeville
+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 ~12.21 miles southwest of Sheffield
  • Midscale Resort property
  • Has environment-friendly policy Read more
More Photos Photo of Interlaken Inn
From£132
Very good 4.0 /5 Latest Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington : 980 Pleasant St.
+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 ~12.56 miles northeast of Sheffield
  • Low-priced property
  • Check-in time: 11:00
More Photos Image of Econo Lodge Lee - Great Barrington
From£35
Average 3.0 /5 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 ~14.29 miles northeast of Sheffield
  • 3 star Rural hotel
  • Free complimentary breakfast
More Photos Image of Applegate Inn
From£118
Very good 4.0 /5 Hotel 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 ~14.36 miles northeast of Sheffield
  • Mid-scale hotel
More Photos Photo of Pilgrim Inn
From£59
Average 3.0 /5 Recent 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 ~14.47 miles northeast of Sheffield
  • Luxury 5-star hotel
More Photos hotel room
From£148
Average 3.0 /5 Review Score Call BookMore Details
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Chambery Inn in 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 ~14.67 miles north of Sheffield
  • Mid-scale property
  • Check in: 14:00
More Photos Exterior of Chambery Inn
From£66
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 ~14.80 miles north of Sheffield
  • 2-star property
  • Check-in: 13:00
More Photos Exterior of Pleasant Valley Motel West Stockbridge
From£44
Average 3.0 /5 Guest Reviews Call BookMore Details
Rodeway Inn in 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 ~15.05 miles north of Sheffield
  • Inexpensive property
  • Check-in: 11:00
More Photos Image of Rodeway Inn
From£44
Average 3.0 /5 Guest 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 Website ~15.33 miles north of Sheffield
  • 3-star Lake hotel
  • Free breakfast
More Photos Exterior of Quality Inn
From£48
Very good 4.0 /5 Read Reviews Call BookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel in Lee
+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 ~15.35 miles north of Sheffield
  • Mid-scale Lake hotel
  • Gym / Fitness Center Available
More Photos Photo of Black Swan Inn Lee Lenox An Ascend Hotel
From£44
Very good 4.0 /5 Review Score Call BookMore Details
Seven Hills Inn - Lenox
+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 ~15.98 miles north of Sheffield
  • High end Resort property
  • Check-in time: 3 pm
More Photos Exterior of Seven Hills Inn
From£136
Very good 4.5 /5 Reviews Call BookMore Details
Wheatleigh - Lenox
+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 ~16.35 miles north of Sheffield
  • Affordable property
  • Free breakfast available
More Photos Photo of Wheatleigh
From£296
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 ~16.59 miles north of Sheffield
  • Mid-scale hotel
  • 2 floors in property
More Photos Photo of Canyon Ranch Lenox
From£66
Average 3.0 /5 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 ~16.89 miles north of Sheffield
  • 4 star Mountain property
  • 3 suites in hotel
More Photos Image of Apple Tree Inn
From£74
Average 3.0 /5 Read Reviews Call BookMore Details
Brook Farm Inn - Lenox
+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 ~17.04 miles north of Sheffield
  • High-end Rural hotel
  • Hotel has 15 rooms
More Photos Exterior of Brook Farm Inn
From£89
Very good 4.0 /5 Reviews Call BookMore Details
Kemble Inn in Lenox
+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 ~17.24 miles north of Sheffield
  • Three Star Mountain property
  • 3 meeting rooms in hotel
More Photos Exterior of Kemble Inn
From£196
Very good 4.0 /5 Latest Reviews Call BookMore Details
The Constance by The Lenox Collection
+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 ~17.29 miles north of Sheffield
  • Four-star hotel
  • Hotel has 3 floors
More Photos Exterior of The Constance by The Lenox Collection
From£166
Average 3.0 /5 Review Score Call BookMore Details
The Whitlock by The Lenox Collection 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 ~17.36 miles north of Sheffield
  • Three Star property
  • 30 rooms in property
More Photos hotel room
From£148
Average 3.0 /5 Latest 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 ~17.80 miles north of Sheffield
  • High end hotel
  • Free breakfast available
More Photos hotel room
From£55
Average 3.0 /5 Recent Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires
+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 ~18.03 miles north of Sheffield
  • Midscale Mountain hotel
  • Free comp. breakfast
More Photos Image of The Cornell Inn, Lenox & The Berkshires
From£44
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Eastover Estate & Retreat : 430 East St.
+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 ~18.59 miles north of Sheffield
  • Four star Mountain property
  • Hotel has a green policy Learn more
More Photos Exterior of Eastover Estate & Retreat
From£80
Average 3.5 /5 Recent Reviews Call BookMore Details
Element Lenox Berkshires in Lenox
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
130 Pittsfield Rd., Lenox, MA 01240 ~19.15 miles north of Sheffield
  • Midscale Mountain property
  • Check-in: 3:00PM
More Photos Image of Element Lenox Berkshires
From£37
Average 3.0 /5 Reviews Call BookMore Details
Life House Berkshires
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
194 Pittsfield Rd., Lenox, MA 01240 ~19.47 miles north of Sheffield
  • Low-priced Suburban property
  • Comp. Breakfast
More Photos Exterior of Life House Berkshires
From£36
Average 3.0 /5 Hotel Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox : 462 Pittsfield Rd.
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
462 Pittsfield Rd., Lenox, MA 01240 ~19.67 miles north of Sheffield
  • 2 star Resort property
  • Free breakfast available
More Photos Photo of Howard Johnson by Wyndham Lenox
From£48
Average 3.0 /5 Review Score Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
55 Lee Rd., Lenox, MA 01240 ~20.19 miles north of Sheffield
  • 4 star Resort property
  • Hotel has 19 suites
More Photos Image of Miraval Berkshires Resort & Spa - All Inclusive Adults Only
From£102
Average 3.0 /5 Latest Reviews Call BookMore Details
The Amselhaus : 6 Rug Rd.
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
6 Rug Rd., Cornwall Bridge, CT 06754 ~20.21 miles south of Sheffield
  • Four-star Riverfront property
  • Free complimentary breakfast
More Photos hotel room
From£185
Very good 4.0 /5 Guest Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
802 State Rd., Richmond, MA 01254 ~20.45 miles north of Sheffield
  • Three Star Rural property
  • Hotel has 12 rooms
More Photos hotel room
From£111
Very good 4.5 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
445 Pittsfield Rd., Lenox, MA 01240 ~20.64 miles north of Sheffield
  • Midscale Mountain property
  • Fitness center on property
More Photos Exterior of Hampton Inn & Suites Berkshires-Lenox
From£80
Average 3.0 /5 Latest Reviews Call BookMore Details
Yankee Inn in Lenox
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
461 Pittsfield Rd., Lenox, MA 01240 ~20.69 miles north of Sheffield
  • Low Cost property
  • 9 suites in property
More Photos Exterior of Yankee Inn
From£107
Very good 4.0 /5 Guest Reviews Call BookMore Details
Knights Inn 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
474 Pittsfield Rd., Lenox, MA 01240 ~20.72 miles north of Sheffield
  • Low-priced Downtown hotel
  • Check-in: 2.00 pm
More Photos Exterior of Knights Inn Lenox
From£27
Poor 2.0 /5 Recent Reviews Call BookMore Details
Lenox Inn - Lenox
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
525 Pittsfield Rd., Lenox, MA 01240 ~20.96 miles north of Sheffield
  • Economical property
  • 18 sleeping rooms in hotel
More Photos Exterior of Lenox Inn
From£44
Poor 2.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1032 South St., Pittsfield, MA 01201 ~21.02 miles north of Sheffield
  • 3 star Suburban property
  • Fitness center on property
More Photos Photo of Hilton Garden Inn Lenox Pittsfield
From£70
Very good 4.0 /5 Review Score Call BookMore Details
Berkshire Mountain Lodge - Pittsfield
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
8 Dan Fox Dr., Pittsfield, MA 01201 ~21.37 miles north of Sheffield
  • Low priced Mountain hotel
  • 2 meeting rooms in hotel
More Photos Image of Berkshire Mountain Lodge
From£92
Very good 4.5 /5 Recent Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
1350 West Housatonic St., Pittsfield, MA 01201 ~22.43 miles north of Sheffield
  • Midscale Rural property
  • 59 rooms in property
More Photos Exterior of Best Western Plus Berkshire Hills Inn & Suites
From£63
Very good 4.5 /5 Recent Reviews Call BookMore Details
Americas Best Value Inn Torrington CT : 395 Winsted Rd.
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
395 Winsted Rd., Torrington, CT 06790 ~23.28 miles southeast of Sheffield
  • Cheap Suburban hotel
  • 30 suites in property
More Photos Exterior of Americas Best Value Inn Torrington CT
From£42
Poor 2.0 /5 Guest Reviews Call BookMore Details
Berkshire Inn
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
150 West Housatonic St., Pittsfield, MA 01201 ~23.49 miles north of Sheffield
  • Inexpensive Downtown property
  • 36 rooms in property
More Photos Photo of Berkshire Inn
From£66
Average 3.0 /5 Read Reviews Call BookMore Details
St. Charles Hotel in Hudson
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
16 Park Place, Hudson, NY 12534 ~23.77 miles west of Sheffield
  • Cheap Downtown property
  • 6 suites in hotel
More Photos Photo of St. Charles Hotel
From£59
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG in Pittsfield
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
1 West St., Pittsfield, MA 01201 ~23.86 miles north of Sheffield
  • Affordable Downtown property
  • Fitness + Health Center
More Photos Image of Holiday Inn & Suites Pittsfield-Berkshires by IHG
From£59
Average 3.0 /5 Recent Reviews Call BookMore Details
Hudson Whaler - Hudson
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
542 Warren St., Hudson, NY 12534 ~23.92 miles west of Sheffield
  • Mid-scale Downtown property
  • 3 floors in hotel
More Photos hotel room
From£55
Very good 4.0 /5 Reviews Call BookMore Details
Hotel on North in Pittsfield
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
297 North St., Pittsfield, MA 01201 ~24.18 miles north of Sheffield
  • High-end Downtown hotel
  • 6 suites in hotel
More Photos Image of Hotel on North
From£111
Excellent 5.0 /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 best IHG hotels in Sheffield?

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

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