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
+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 +1-888-389-4121 ~4.59 miles northwest of Sheffield
  • Affordable Mountain hotel
  • Hotel has 13 rooms
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From£137
Excellent 5.0 /5 Latest Reviews Call BookMore Details
Quality Inn 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
  • Inexpensive Rural property
  • 63 sleeping rooms in hotel
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From£74
Very good 4.0 /5 Read 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 +1-800-716-8490 ~6.69 miles north of Sheffield
  • Mid-scale Resort property
  • Check in time: 3:00pm
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From£81
Very good 4.0 /5 Latest 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 +1-800-805-5223 ~7.03 miles north of Sheffield
  • 2-star Resort property
  • Check-in: 11:00 AM
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From£35
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Great Barrington - 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 +1-888-965-1860 ~7.13 miles north of Sheffield
  • 3-star Mountain hotel
  • Hotel has 3 floors
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From£66
Very good 4.0 /5 Review Score 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 +1-888-788-5576 ~9.30 miles southeast of Sheffield
  • 3 star property
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From£81
Very good 4.0 /5 Review Score 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 +1-888-897-9207 ~11.30 miles southwest of Sheffield
  • Affordable Rural hotel
  • Check-in time: 3 pm
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From£66
Average 3.0 /5 Recent Reviews Call BookMore Details
Manor House Inn in Norfolk
+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 hotel
  • Complimentary breakfast is offered
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From£178
Very good 4.0 /5 Guest 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 +1-888-469-4795 ~12.00 miles north of Sheffield
  • Mid-scale Rural hotel
  • 8 meeting rooms in hotel
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From£59
Average 3.0 /5 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 +1-888-734-9421 ~12.04 miles north of Sheffield
  • Affordable Mountain hotel
  • 334 rooms in property
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From£66
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Interlaken Inn
+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 +1-888-841-5292 ~12.21 miles southwest of Sheffield
  • Affordable Resort hotel
  • 86 rooms in property
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From£133
Very good 4.0 /5 Read Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington - 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 +1-888-455-5160 ~12.56 miles northeast of Sheffield
  • Cheap property
  • Hotel has 28 rooms
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From£35
Average 3.0 /5 Hotel 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 property
  • Check-in time: 2 pm
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From£119
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Pilgrim Inn
+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
  • 3-star hotel
  • Check in: 3:00 PM
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From£59
Average 3.0 /5 Read 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 +1-888-749-6785 ~14.47 miles northeast of Sheffield
  • Luxurious 5-star hotel
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From£149
Average 3.0 /5 Recent Reviews Call BookMore Details
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 +1-888-878-9982 ~14.67 miles north of Sheffield
  • Midscale hotel
  • Hotel has 9 rooms
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From£67
Very good 4.5 /5 Hotel Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge : 42 Stockbridge Rd.
+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 +1-888-389-4485 ~14.80 miles north of Sheffield
  • 2 star property
  • Check-in: 13:00
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From£44
Average 3.0 /5 Hotel Reviews Call BookMore Details
Rodeway Inn : 200 Laurel St.
+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 +1-888-389-4121 ~15.05 miles north of Sheffield
  • Cheap property
  • 23 rooms in hotel
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From£44
Average 3.0 /5 Recent 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 Website +1-888-675-2083 ~15.33 miles north of Sheffield
  • Affordable Lake hotel
  • Check-in time: 3:00 PM
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From£48
Very good 4.0 /5 Latest 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 +1-800-716-8490 ~15.35 miles north of Sheffield
  • Affordable Lake property
  • Access to gym on-site
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From£44
Very good 4.0 /5 Latest 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
  • Expensive Resort property
  • 2 floors in hotel
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From£137
Very good 4.5 /5 Recent 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 +1-888-965-1860 ~16.35 miles north of Sheffield
  • 3 star property
  • Free breakfast available
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From£298
Very good 4.0 /5 Review Score 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 +1-888-788-5576 ~16.59 miles north of Sheffield
  • Mid-scale property
  • 102 rooms in hotel
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From£67
Average 3.0 /5 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 hotel
  • 34 sleeping rooms in hotel
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From£74
Average 3.0 /5 Latest 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 +1-888-311-4278 ~17.04 miles north of Sheffield
  • 4-star Rural property
  • Hotel has an eco-friendly policy Read more
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From£89
Very good 4.0 /5 Recent 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 +1-888-469-4795 ~17.24 miles north of Sheffield
  • Affordable Mountain property
  • Hotel has a green policy See policy
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From£197
Very good 4.0 /5 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
  • Four star hotel
  • Hotel has 3 floors
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From£167
Average 3.0 /5 Hotel 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
  • 30 sleeping rooms in hotel
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From£149
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
  • 4 star property
  • Hotel has 2 floors
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From£55
Average 3.0 /5 Review Score Call BookMore Details
The Cornell Inn, Lenox & The Berkshires : 203 Main St.
+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 breakfast
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From£44
Very good 4.0 /5 Recent Reviews Call BookMore Details
Eastover Estate & Retreat
+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£81
Average 3.5 /5 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
  • Affordable Mountain property
  • Check-in time: 3:00PM
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From£37
Average 3.0 /5 Latest Reviews Call BookMore Details
Life House Berkshires - Lenox
+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
  • Low-priced Suburban property
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From£36
Average 3.0 /5 Guest Reviews Call BookMore Details
Howard Johnson by Wyndham 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 Reviews 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 +1-888-389-4121 ~20.19 miles north of Sheffield
  • Four star Resort hotel
  • Hotel has a green policy Learn more
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From£102
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Amselhaus - 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
  • Four-star Riverfront hotel
  • 2 floors in hotel
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From£186
Very good 4.0 /5 Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center : 802 State Rd.
+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
  • Midscale Rural hotel
  • 3 floors in property
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From£111
Very good 4.5 /5 Guest Reviews 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
  • 24 suites in property
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From£81
Average 3.0 /5 Read Reviews Call BookMore Details
The Yankee, Trademark Collection by Wyndham 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
  • Low priced hotel
  • 3 floors in hotel
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From£108
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 +1-888-788-5576 ~20.72 miles north of Sheffield
  • Low priced Downtown hotel
  • 16 rooms in hotel
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From£27
Poor 2.0 /5 Read Reviews Call BookMore Details
Lenox Inn
+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
  • Economical property
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From£44
Poor 2.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1055 South St., Pittsfield, MA 01201 +1-888-311-4278 ~21.02 miles north of Sheffield
  • Affordable Suburban property
  • Free comp. breakfast
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From£59
Average 3.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield : 1032 South St.
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
1032 South St., Pittsfield, MA 01201 +1-888-469-4795 ~21.02 miles north of Sheffield
  • 3-star Suburban hotel
  • Hotel has 4 floors
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From£70
Very good 4.0 /5 Latest Reviews Call BookMore Details
Berkshire Mountain Lodge
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
8 Dan Fox Dr., Pittsfield, MA 01201 +1-888-734-9421 ~21.37 miles north of Sheffield
  • Cheap Mountain property
  • 2 conference rooms in property
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From£93
Very good 4.5 /5 Latest Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites - Pittsfield
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
1350 West Housatonic St., Pittsfield, MA 01201 +1-888-841-5292 ~22.43 miles north of Sheffield
  • 3 star Rural hotel
  • 3 floors in hotel
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From£63
Very good 4.5 /5 Reviews Call BookMore Details
Americas Best Value Inn Torrington CT
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
395 Winsted Rd., Torrington, CT 06790 +1-888-455-5160 ~23.28 miles southeast of Sheffield
  • 2-star Suburban property
  • Check-in time: 3:00pm
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From£42
Poor 2.0 /5 Reviews Call BookMore Details
Berkshire Inn : 150 West Housatonic St.
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
150 West Housatonic St., Pittsfield, MA 01201 +1-888-965-8297 ~23.49 miles north of Sheffield
  • Two star Downtown property
  • Check in: 1500
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From£67
Average 3.0 /5 Recent Reviews Call BookMore Details
St. Charles Hotel
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
16 Park Place, Hudson, NY 12534 +1-888-906-6358 ~23.77 miles west of Sheffield
  • Low priced Downtown hotel
  • Hotel has 34 rooms
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From£59
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
1 West St., Pittsfield, MA 01201 +1-888-749-6785 ~23.86 miles north of Sheffield
  • Three Star Downtown hotel
  • Check in time: 3:00 PM
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From£59
Average 3.0 /5 Read Reviews Call BookMore Details
Hudson Whaler
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
542 Warren St., Hudson, NY 12534 +1-888-878-9982 ~23.92 miles west of Sheffield
  • Three Star Downtown property
  • 16 rooms in property
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From£55
Very good 4.0 /5 Guest Reviews Call BookMore Details

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