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
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
684 South Egremont Rd., Great Barrington, MA 01230 +1-888-389-4121 ~4.59 miles northwest of Sheffield
  • 3-star Mountain property
  • 2 floors in hotel
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From£137
Excellent 5.0 /5 Guest Reviews Call BookMore Details
Quality Inn in Great Barrington
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
372 Main St., Great Barrington, MA 01230 Website +1-888-675-2083 ~5.61 miles north of Sheffield
  • Low priced Rural property
  • Hotel has 63 rooms
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From£74
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi - Great Barrington
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
249 Stockbridge Rd., Great Barrington, MA 01230 Website +1-800-716-8490 ~6.69 miles north of Sheffield
  • Three Star Resort hotel
  • Check-in: 3:00pm
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From£80
Very good 4.0 /5 Guest Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
400 Stockbridge Rd., Great Barrington, MA 01230 +1-800-805-5223 ~7.03 miles north of Sheffield
  • Economy Resort property
  • Free comp. breakfast
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From£34
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Express Great Barrington in Great Barrington
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
415 Stockbridge Rd., Great Barrington, MA 01230 +1-888-965-1860 ~7.13 miles north of Sheffield
  • Mid-scale Mountain hotel
  • Hotel has an eco-friendly policy See more
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From£66
Very good 4.0 /5 Review Score Call BookMore Details
Blackberry River Inn : 538 Greenwoods Rd. West
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
538 Greenwoods Rd. West, Norfolk, CT 06058 +1-888-788-5576 ~9.30 miles southeast of Sheffield
  • Three Star hotel
  • Check-in: 15:00
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From£80
Very good 4.0 /5 Read Reviews Call BookMore Details
Wake Robin Inn in Lakeville
+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 +1-888-897-9207 ~11.30 miles southwest of Sheffield
  • Affordable Rural hotel
  • Hotel has an eco-friendly policy See more
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From£66
Average 3.0 /5 Reviews Call BookMore Details
Manor House Inn
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
69 Maple Ave., Norfolk, CT 06058 +1-888-311-4278 ~11.55 miles southeast of Sheffield
  • 3 star Rural property
  • Check in: 3:00pm
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From£178
Very good 4.0 /5 Recent Reviews Call BookMore Details
The Red Lion Inn - Stockbridge
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
30 Main St., Stockbridge, MA 01262 +1-888-469-4795 ~12.00 miles north of Sheffield
  • 3-star Rural property
  • Hotel has 8 meeting rooms
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From£59
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
190 Meadow St., South Lee, MA 01260 +1-888-734-9421 ~12.04 miles north of Sheffield
  • 3-star Mountain property
  • 334 sleeping rooms in hotel
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From£66
Very good 4.0 /5 Latest Reviews Call BookMore Details
Interlaken Inn
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
74 Interlaken Rd., Lakeville, CT 06039 +1-888-841-5292 ~12.21 miles southwest of Sheffield
  • Three Star Resort hotel
  • Free breakfast
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From£132
Very good 4.0 /5 Read Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
980 Pleasant St., Lee, MA 01238 +1-888-455-5160 ~12.56 miles northeast of Sheffield
  • 2-star property
  • Check in: 11:00
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From£35
Average 3.0 /5 Latest Reviews Call BookMore Details
Applegate Inn
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
279 West Park St., Lee, MA 01238 +1-888-965-8297 ~14.29 miles northeast of Sheffield
  • 3-star Rural hotel
  • Hotel has 3 floors
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From£118
Very good 4.0 /5 Guest Reviews Call BookMore Details
Pilgrim Inn : 165 Housatonic St.
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
165 Housatonic St., Lee, MA 01238 +1-888-906-6358 ~14.36 miles northeast of Sheffield
  • Three Star hotel
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From£59
Average 3.0 /5 Latest Reviews Call BookMore Details
33 Main in Lenox
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
33 Main St., Lenox, MA 01238 +1-888-749-6785 ~14.47 miles northeast of Sheffield
  • Luxurious Five Star hotel
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From£148
Average 3.0 /5 Guest Reviews Call BookMore Details
Chambery Inn - Lee
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
199 Main St., Lee, 01238 +1-888-878-9982 ~14.67 miles north of Sheffield
  • Affordable hotel
  • 9 rooms in property
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From£66
Very good 4.5 /5 Recent Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge : 42 Stockbridge Rd.
+1-888-389-4485

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New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
42 Stockbridge Rd., West Stockbridge, MA 01266 +1-888-389-4485 ~14.80 miles north of Sheffield
  • Economical hotel
  • Check in: 13:00
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From£44
Average 3.0 /5 Read Reviews Call BookMore Details
Rodeway Inn
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
200 Laurel St., Lee, MA 01238 +1-888-389-4121 ~15.05 miles north of Sheffield
  • Economical hotel
  • 23 rooms in property
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From£44
Average 3.0 /5 Review Score 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 +1-888-675-2083 ~15.33 miles north of Sheffield
  • 3-star Lake hotel
  • Check in: 3:00 PM
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From£48
Very good 4.0 /5 Read 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 +1-800-716-8490 ~15.35 miles north of Sheffield
  • Affordable Lake property
  • 2 floors in hotel
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From£44
Very good 4.0 /5 Read Reviews 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 +1-800-805-5223 ~15.98 miles north of Sheffield
  • High end Resort hotel
  • 57 rooms in property
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From£136
Very good 4.5 /5 Guest Reviews Call BookMore Details
Wheatleigh
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
Hawthorne Rd., Lenox, MA 01240 +1-888-965-1860 ~16.35 miles north of Sheffield
  • 3 star hotel
  • 9 suites in property
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From£296
Very good 4.0 /5 Review Score 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 +1-888-788-5576 ~16.59 miles north of Sheffield
  • 3-star property
  • 2 floors in hotel
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From£66
Average 3.0 /5 Hotel 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 +1-888-897-9207 ~16.89 miles north of Sheffield
  • Four star Mountain property
  • 3 suites in property
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From£74
Average 3.0 /5 Reviews Call BookMore Details
Brook Farm Inn in 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 +1-888-311-4278 ~17.04 miles north of Sheffield
  • High end Rural property
  • Hotel has an eco-friendly policy See more
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From£89
Very good 4.0 /5 Latest 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 +1-888-469-4795 ~17.24 miles north of Sheffield
  • 3 star Mountain property
  • Has environment-friendly policy Learn more
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From£196
Very good 4.0 /5 Hotel 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 +1-888-734-9421 ~17.29 miles north of Sheffield
  • Expensive hotel
  • Free breakfast
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From£166
Average 3.0 /5 Recent Reviews Call BookMore Details
The Whitlock by The Lenox Collection
+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 +1-888-841-5292 ~17.36 miles north of Sheffield
  • 3 star property
  • Check in time: 14:00
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From£148
Average 3.0 /5 Review Score Call BookMore Details
The Dewey by The Lenox Collection : 7 Hubbard St.
+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 +1-888-455-5160 ~17.80 miles north of Sheffield
  • High-end hotel
  • Comp. Breakfast
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From£55
Average 3.0 /5 Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires 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 +1-888-965-8297 ~18.03 miles north of Sheffield
  • Three Star Mountain property
  • Free complimentary breakfast
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From£44
Very good 4.0 /5 Guest 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 +1-888-906-6358 ~18.59 miles north of Sheffield
  • High-end Mountain hotel
  • Check-in time: 4:00PM
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From£80
Average 3.5 /5 Latest Reviews Call BookMore Details
Element Lenox Berkshires
+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 +1-888-749-6785 ~19.15 miles north of Sheffield
  • Midscale Mountain hotel
  • Comp. Breakfast
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From£37
Average 3.0 /5 Guest 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 +1-888-878-9982 ~19.47 miles north of Sheffield
  • Economical Suburban property
  • Check-in time: 2pm
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From£36
Average 3.0 /5 Review Score Call BookMore Details
Howard Johnson by Wyndham Lenox - Lenox
+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 +1-888-389-4485 ~19.67 miles north of Sheffield
  • 2-star Resort property
  • 2 floors in property
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From£48
Average 3.0 /5 Recent Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only in Lenox
+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 +1-888-389-4121 ~20.19 miles north of Sheffield
  • 4-star Resort hotel
  • 10 conference rooms in property
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From£102
Average 3.0 /5 Read Reviews Call BookMore Details
The Amselhaus in Cornwall Bridge
+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 +1-888-675-2083 ~20.21 miles south of Sheffield
  • Expensive Riverfront property
  • Check-in time: 0:00 pm
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From£185
Very good 4.0 /5 Latest 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 +1-800-716-8490 ~20.45 miles north of Sheffield
  • Affordable Rural hotel
  • Check-in: 3:00 p.m.
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From£111
Very good 4.5 /5 Review Score Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox : 445 Pittsfield Rd.
+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 +1-800-805-5223 ~20.64 miles north of Sheffield
  • Affordable Mountain property
  • Free breakfast available
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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 +1-888-965-1860 ~20.69 miles north of Sheffield
  • Economical hotel
  • Hotel has 3 floors
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From£107
Very good 4.0 /5 Recent Reviews Call BookMore Details
Knights Inn 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 +1-888-788-5576 ~20.72 miles north of Sheffield
  • Low Cost Downtown property
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From£27
Poor 2.0 /5 Hotel Reviews Call BookMore Details
Lenox Inn : 525 Pittsfield Rd.
+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 +1-888-897-9207 ~20.96 miles north of Sheffield
  • Low priced property
  • 18 sleeping rooms in hotel
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From£44
Poor 2.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Lenox Pittsfield in 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 +1-888-311-4278 ~21.02 miles north of Sheffield
  • 3 star Suburban property
  • 3 suites in hotel
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From£70
Very good 4.0 /5 Review Score Call BookMore Details
Berkshire Mountain Lodge
+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 +1-888-469-4795 ~21.37 miles north of Sheffield
  • Cheap Mountain property
  • 5 floors in hotel
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From£92
Very good 4.5 /5 Guest Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites in Pittsfield
+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 +1-888-734-9421 ~22.43 miles north of Sheffield
  • Midscale Rural hotel
  • Free breakfast
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From£63
Very good 4.5 /5 Latest Reviews Call BookMore Details
Americas Best Value Inn Torrington CT
+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 +1-888-841-5292 ~23.28 miles southeast of Sheffield
  • Cheap Suburban hotel
  • 91 sleeping rooms in hotel
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From£42
Poor 2.0 /5 Guest Reviews Call BookMore Details
Berkshire Inn - Pittsfield
+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 +1-888-455-5160 ~23.49 miles north of Sheffield
  • Two star Downtown hotel
  • Fitness + Health Center
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From£66
Average 3.0 /5 Guest 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 +1-888-965-8297 ~23.77 miles west of Sheffield
  • Cheap Downtown hotel
  • Free breakfast available
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From£59
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG : 1 West St.
+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 +1-888-906-6358 ~23.86 miles north of Sheffield
  • Affordable Downtown hotel
  • Fitness center on property
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From£59
Average 3.0 /5 Read Reviews Call BookMore Details
Hudson Whaler
+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 +1-888-749-6785 ~23.92 miles west of Sheffield
  • Mid-scale Downtown property
  • 16 rooms in property
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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 +1-888-878-9982 ~24.18 miles north of Sheffield
  • Four star Downtown hotel
  • Check-in: 15:00
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From£111
Excellent 5.0 /5 Latest Reviews Call BookMore Details

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