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 hotel
  • 13 rooms in property
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From£136
Excellent 5.0 /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
372 Main St., Great Barrington, MA 01230 Website +1-888-675-2083 ~5.62 miles north of Sheffield
  • Cheap Rural property
  • Gym / Fitness Center Available
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From£73
Very good 4.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
+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 ~6.70 miles north of Sheffield
  • Three Star Resort hotel
  • Free complimentary breakfast
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From£80
Very good 4.0 /5 Guest 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 ~7.04 miles north of Sheffield
  • Inexpensive Resort hotel
  • Free comp. breakfast
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From£34
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express 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
  • Three Star Mountain property
  • Hotel has 3 floors
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From£65
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
  • Mid-scale property
  • 17 rooms in hotel
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From£80
Very good 4.0 /5 Guest 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
  • Affordable Rural hotel
  • 3 meeting rooms in property
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From£65
Average 3.0 /5 Reviews Call BookMore Details
Manor House Inn : 69 Maple Ave.
+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 +1-888-311-4278 ~11.57 miles southeast of Sheffield
  • Mid-scale Rural property
  • Hotel has 9 rooms
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From£176
Very good 4.0 /5 Read Reviews 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
  • Midscale Rural property
  • Check in time: 3:00
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From£58
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort - 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
  • 3-star Mountain property
  • Fitness / Gym is on-site
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From£65
Very good 4.0 /5 Read Reviews Call BookMore Details
Interlaken Inn & Resort - 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 +1-888-841-5292 ~12.19 miles southwest of Sheffield
  • 3-star Resort property
  • Check in time: 4:00 pm
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From£154
Very good 4.0 /5 Review Score 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 +1-888-455-5160 ~12.58 miles northeast of Sheffield
  • Economical hotel
  • Check in time: 11:00
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From£35
Average 3.0 /5 Read 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£117
Very good 4.0 /5 Latest 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 ~14.37 miles northeast of Sheffield
  • 3-star hotel
  • Check-in time: 3:00 PM
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From£58
Average 3.0 /5 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 ~14.49 miles northeast of Sheffield
  • Luxury 5 star property
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From£147
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 ~14.69 miles north of Sheffield
  • Midscale hotel
  • Check-in: 14:00
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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

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 priced property
  • 16 sleeping rooms in hotel
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From£44
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 +1-888-389-4121 ~15.07 miles north of Sheffield
  • Low Cost property
  • Check-in time: 11:00
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From£44
Average 3.0 /5 Hotel Reviews Call BookMore Details
Quality Inn in 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 ~15.35 miles north of Sheffield
  • 3-star Lake hotel
  • 52 sleeping rooms in hotel
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From£47
Very good 4.0 /5 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 ~15.36 miles north of Sheffield
  • Three Star Lake property
  • Free breakfast available
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From£44
Very good 4.0 /5 Recent Reviews Call BookMore Details
Seven Hills Inn in 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 ~16.00 miles north of Sheffield
  • High end Resort hotel
  • 4 suites in property
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From£135
Very good 4.5 /5 Guest Reviews Call BookMore Details
Wheatleigh : Hawthorne Rd.
+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
  • Midscale hotel
  • Comp. Breakfast
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From£294
Very good 4.0 /5 Guest 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 +1-888-788-5576 ~16.61 miles north of Sheffield
  • Three Star hotel
  • Check in: 15:00
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From£66
Average 3.0 /5 Latest 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 +1-888-897-9207 ~16.91 miles north of Sheffield
  • 4-star Mountain hotel
  • Check-in time: 4:00 PM
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From£73
Average 3.0 /5 Guest 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 ~17.06 miles north of Sheffield
  • High-end Rural property
  • Free comp. breakfast
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From£88
Very good 4.0 /5 Guest Reviews Call BookMore Details
Kemble Inn - 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
  • Mid-scale Mountain property
  • 3 floors in property
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From£195
Very good 4.0 /5 Guest 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 ~17.31 miles north of Sheffield
  • Four star property
  • Hotel has 3 floors
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From£165
Average 3.0 /5 Latest 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 +1-888-841-5292 ~17.38 miles north of Sheffield
  • Mid-scale hotel
  • Hotel has 30 rooms
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From£147
Average 3.0 /5 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 +1-888-455-5160 ~17.83 miles north of Sheffield
  • High-end property
  • Hotel has 12 rooms
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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 ~18.06 miles north of Sheffield
  • Mid-scale Mountain property
  • Comp. Breakfast
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From£44
Very good 4.0 /5 Read 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 ~18.62 miles north of Sheffield
  • High-end Mountain property
  • Hotel has an eco-friendly policy See more
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From£80
Average 3.5 /5 Hotel Reviews Call BookMore Details
Life House Berkshires - 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
  • Cheap Suburban hotel
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From£36
Average 3.0 /5 Guest 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 +1-888-878-9982 ~19.70 miles north of Sheffield
  • Inexpensive Resort property
  • Complimentary breakfast is offered
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From£47
Average 3.0 /5 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 +1-888-389-4485 ~20.22 miles north of Sheffield
  • Four-star Resort hotel
  • Hotel has an eco-friendly policy See more
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From£101
Average 3.0 /5 Latest Reviews Call BookMore Details
The Amselhaus in 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 +1-888-389-4121 ~20.24 miles south of Sheffield
  • 4-star Riverfront hotel
  • 2 floors in hotel
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From£184
Very good 4.0 /5 Guest Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center - 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 +1-888-675-2083 ~20.48 miles north of Sheffield
  • Three Star Rural property
  • 4 suites in hotel
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From£110
Very good 4.5 /5 Review Score 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 +1-800-716-8490 ~20.67 miles north of Sheffield
  • Midscale Mountain hotel
  • 3 floors in hotel
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From£80
Average 3.0 /5 Guest Reviews Call BookMore Details
Yankee Inn in Lenox
+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
  • Two-star hotel
  • 9 suites in property
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From£106
Very good 4.0 /5 Guest Reviews Call BookMore Details
Knights Inn Lenox in 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
  • Two-star Downtown property
  • Check-in time: 2.00 pm
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From£27
Poor 2.0 /5 Review Score Call BookMore Details
Lenox Inn : 525 Pittsfield Rd.
+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
  • 2 star property
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From£44
Poor 2.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield : 1032 South St.
+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
  • Midscale Suburban property
  • Gym is available on property
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From£70
Very good 4.0 /5 Recent 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
  • Cheap Mountain hotel
  • Gym / Fitness Center Available
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From£92
Very good 4.5 /5 Recent 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
  • Affordable Rural hotel
  • Fitness + Health Center
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From£58
Very good 4.0 /5 Review Score Call BookMore Details
Americas Best Value Inn Torrington CT in Torrington
+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
  • Low-priced Suburban property
  • 91 sleeping rooms in hotel
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From£42
Poor 2.0 /5 Latest Reviews Call BookMore Details
Berkshire Inn in 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
  • Economical Downtown property
  • Check-in: 1500
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From£66
Average 3.0 /5 Guest Reviews Call BookMore Details
St. Charles Hotel in Hudson
+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 hotel
  • Hotel has 3 floors
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From£58
Average 3.0 /5 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
  • 26 suites in property
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From£58
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hudson Whaler - 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
  • 3-star Downtown hotel
  • Fitness + Health Center
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From£55
Very good 4.0 /5 Read 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
  • High-end Downtown hotel
  • Hotel has an eco-friendly policy Read more
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From£110
Excellent 5.0 /5 Recent Reviews Call BookMore Details
The Nest Hudson Hotel
+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
  • 4-star Downtown property
  • 6 rooms in property
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From£147
Very good 4.5 /5 Review Score Call BookMore Details

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