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 in Great Barrington
+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 ~4.60 miles northwest of Sheffield
  • 3-star Mountain property
  • Hotel has 2 meeting rooms
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From£142
Excellent 5.0 /5 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
372 Main St., Great Barrington, MA 01230 Website +1-888-675-2083 ~5.62 miles north of Sheffield
  • Cheap Rural hotel
  • Check in: 3:00pm
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From£77
Very good 4.0 /5 Latest 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 +1-800-716-8490 ~6.70 miles north of Sheffield
  • Affordable Resort property
  • Gym is available on property
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From£84
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 +1-800-805-5223 ~7.04 miles north of Sheffield
  • Cheap Resort hotel
  • Free breakfast available
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From£36
Average 3.0 /5 Read 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 +1-888-965-1860 ~7.14 miles north of Sheffield
  • 3-star Mountain hotel
  • Free comp. breakfast
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From£68
Very good 4.0 /5 Latest 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 +1-888-788-5576 ~9.32 miles southeast of Sheffield
  • 3-star hotel
  • Check-in: 15:00
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From£84
Very good 4.0 /5 Recent 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 ~11.32 miles southwest of Sheffield
  • Midscale Rural property
  • Check-in: 3 pm
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From£68
Average 3.0 /5 Latest Reviews Call BookMore Details
Manor House Inn : 69 Maple Ave.
+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 ~11.57 miles southeast of Sheffield
  • 3-star Rural hotel
  • Free breakfast available
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From£185
Very good 4.0 /5 Review Score Call BookMore Details
The Red Lion Inn : 30 Main St.
+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 ~12.02 miles north of Sheffield
  • 3-star Rural hotel
  • 4 floors in hotel
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From£61
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort in South Lee
+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 ~12.06 miles north of Sheffield
  • Three Star Mountain hotel
  • Gym / Fitness Center Available
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From£68
Very good 4.0 /5 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 +1-888-841-5292 ~12.19 miles southwest of Sheffield
  • Three Star Resort hotel
  • Hotel has 86 rooms
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From£161
Very good 4.0 /5 Hotel 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 +1-888-455-5160 ~12.58 miles northeast of Sheffield
  • Two star hotel
  • 28 rooms in property
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From£37
Average 3.0 /5 Hotel Reviews Call BookMore Details
Applegate Inn - Lee
+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 ~14.31 miles northeast of Sheffield
  • Three Star Rural hotel
  • Check in: 2 pm
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From£123
Very good 4.0 /5 Latest Reviews Call BookMore Details
Pilgrim Inn in Lee
+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 ~14.37 miles northeast of Sheffield
  • Mid-scale hotel
  • Check-in time: 3:00 PM
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From£61
Average 3.0 /5 Recent Reviews Call BookMore Details
33 Main
+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 ~14.49 miles northeast of Sheffield
  • Luxurious Five Star hotel
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From£154
Average 3.0 /5 Latest Reviews Call BookMore Details
Chambery Inn
+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 ~14.69 miles north of Sheffield
  • 3-star hotel
  • 9 rooms in hotel
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From£69
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 ~14.83 miles north of Sheffield
  • Low Cost property
  • Check in time: 13:00
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From£46
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 ~15.07 miles north of Sheffield
  • Cheap hotel
  • 23 sleeping rooms in hotel
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From£46
Average 3.0 /5 Latest Reviews Call BookMore Details
Quality Inn : 435 Laurel St.
+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 +1-888-675-2083 ~15.35 miles north of Sheffield
  • Mid-scale Lake hotel
  • Gym / Fitness Center Available
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From£50
Very good 4.0 /5 Guest Reviews Call BookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel - 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 ~15.36 miles north of Sheffield
  • Affordable Lake property
  • Free comp. breakfast
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From£46
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 +1-800-805-5223 ~16.00 miles north of Sheffield
  • 4-star Resort hotel
  • Hotel has 2 floors
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From£141
Very good 4.5 /5 Guest 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 +1-888-965-1860 ~16.37 miles north of Sheffield
  • Mid-scale property
  • Free breakfast available
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From£308
Very good 4.0 /5 Latest Reviews 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 +1-888-788-5576 ~16.61 miles north of Sheffield
  • Three Star property
  • Fitness + Health Center
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From£69
Average 3.0 /5 Read Reviews Call BookMore Details
Apple Tree Inn - 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 ~16.91 miles north of Sheffield
  • High-end Mountain hotel
  • Check-in: 4:00 PM
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From£77
Average 3.0 /5 Hotel 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 +1-888-311-4278 ~17.06 miles north of Sheffield
  • Four star Rural hotel
  • Hotel has an eco-friendly policy Learn more
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From£92
Very good 4.0 /5 Read 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 ~17.26 miles north of Sheffield
  • 3 star Mountain property
  • Hotel has 12 suites
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From£204
Very good 4.0 /5 Guest 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 +1-888-734-9421 ~17.31 miles north of Sheffield
  • High end hotel
  • Hotel has 24 rooms
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From£173
Average 3.0 /5 Hotel Reviews 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 +1-888-841-5292 ~17.38 miles north of Sheffield
  • Midscale property
  • Check in time: 14:00
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From£154
Average 3.0 /5 Read Reviews Call BookMore Details
The Dewey by The Lenox Collection in Lenox
+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 ~17.83 miles north of Sheffield
  • 4-star property
  • 2 floors in property
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From£57
Average 3.0 /5 Read Reviews Call BookMore Details
The Cornell Inn 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 ~18.06 miles north of Sheffield
  • Mid-scale Mountain hotel
  • 28 sleeping rooms in hotel
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From£46
Very good 4.0 /5 Recent Reviews Call BookMore Details
Eastover Estate & Retreat - 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 +1-888-906-6358 ~18.62 miles north of Sheffield
  • Four-star Mountain property
  • Hotel has 90 rooms
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From£84
Average 3.5 /5 Reviews Call BookMore Details
Life House 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
194 Pittsfield Rd., Lenox, MA 01240 +1-888-749-6785 ~19.49 miles north of Sheffield
  • Low Cost Suburban hotel
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From£37
Average 3.0 /5 Latest Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox : 462 Pittsfield Rd.
+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 +1-888-878-9982 ~19.70 miles north of Sheffield
  • Two-star Resort property
  • Free complimentary breakfast
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From£50
Average 3.0 /5 Guest Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only
+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 +1-888-389-4485 ~20.22 miles north of Sheffield
  • High end Resort hotel
  • Check-in: 3PM
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From£106
Average 3.0 /5 Latest Reviews Call BookMore Details
The Amselhaus : 6 Rug Rd.
+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 +1-888-389-4121 ~20.24 miles south of Sheffield
  • 4-star Riverfront property
  • Check-in time: 0:00 pm
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From£192
Very good 4.0 /5 Read Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center
+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 +1-888-675-2083 ~20.48 miles north of Sheffield
  • Three Star Rural hotel
  • 4 suites in hotel
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From£115
Very good 4.5 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox - 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 +1-800-716-8490 ~20.67 miles north of Sheffield
  • Three Star Mountain hotel
  • Check-in time: 3:00 pm
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From£84
Average 3.0 /5 Read 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 +1-800-805-5223 ~20.72 miles north of Sheffield
  • Low-priced hotel
  • Hotel has 96 rooms
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From£111
Very good 4.0 /5 Review Score Call BookMore Details
Knights Inn Lenox - 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 +1-888-965-1860 ~20.75 miles north of Sheffield
  • Inexpensive Downtown property
  • Hotel has 16 rooms
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From£28
Poor 2.0 /5 Read Reviews Call BookMore Details
Lenox Inn in 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 +1-888-788-5576 ~20.99 miles north of Sheffield
  • Low Cost property
  • Check in time: 15:00
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From£46
Poor 2.0 /5 Hotel Reviews 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 +1-888-897-9207 ~21.05 miles north of Sheffield
  • Three Star Suburban property
  • Hotel has 95 rooms
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From£73
Very good 4.0 /5 Guest Reviews Call BookMore Details
Berkshire Mountain Lodge in Pittsfield
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
8 Dan Fox Dr., Pittsfield, MA 01201 +1-888-311-4278 ~21.40 miles north of Sheffield
  • Two star Mountain property
  • 5 floors in hotel
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From£96
Very good 4.5 /5 Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
1350 West Housatonic St., Pittsfield, MA 01201 +1-888-469-4795 ~22.47 miles north of Sheffield
  • Midscale Rural property
  • Fitness / Gym is on-site
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From£60
Very good 4.0 /5 Recent Reviews Call BookMore Details
Americas Best Value Inn Torrington CT
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
395 Winsted Rd., Torrington, CT 06790 +1-888-734-9421 ~23.33 miles southeast of Sheffield
  • 2-star Suburban hotel
  • Free complimentary breakfast
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From£43
Poor 2.0 /5 Latest Reviews Call BookMore Details
Berkshire Inn - Pittsfield
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
150 West Housatonic St., Pittsfield, MA 01201 +1-888-841-5292 ~23.52 miles north of Sheffield
  • Economy Downtown property
  • Fitness center on property
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From£69
Average 3.0 /5 Review Score Call BookMore Details
St. Charles Hotel : 16 Park Place
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
16 Park Place, Hudson, NY 12534 +1-888-455-5160 ~23.78 miles west of Sheffield
  • 2 star Downtown property
  • Hotel has 3 floors
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From£61
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG : 1 West St.
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
1 West St., Pittsfield, MA 01201 +1-888-965-8297 ~23.89 miles north of Sheffield
  • 3 star Downtown property
  • Check in time: 3:00 PM
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From£61
Average 3.0 /5 Reviews Call BookMore Details
Hudson Whaler in Hudson
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
542 Warren St., Hudson, NY 12534 +1-888-906-6358 ~23.93 miles west of Sheffield
  • Affordable Downtown property
  • 3 floors in hotel
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From£57
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hotel on North
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
297 North St., Pittsfield, MA 01201 +1-888-749-6785 ~24.21 miles north of Sheffield
  • Four star Downtown property
  • Hotel has an eco-friendly policy Read more
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From£115
Excellent 5.0 /5 Latest Reviews Call BookMore Details
The Nest Hudson Hotel : 330 Union St.
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
330 Union St., Hudson, NY 12534 +1-888-878-9982 ~24.29 miles west of Sheffield
  • Four-star Downtown property
  • Check in time: 3:00
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From£154
Very good 4.5 /5 Hotel Reviews Call BookMore Details

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