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 +1-888-389-4121 ~4.60 miles northwest of Sheffield
  • Midscale Mountain property
  • 13 rooms in property
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From£139
Excellent 5.0 /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
372 Main St., Great Barrington, MA 01230 Website +1-888-675-2083 ~5.62 miles north of Sheffield
  • 2-star Rural property
  • Fitness center on property
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From£75
Very good 4.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi in 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 ~6.70 miles north of Sheffield
  • Midscale Resort property
  • 3 floors in property
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From£82
Very good 4.0 /5 Reviews 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 property
  • Check-in time: 11:00 AM
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From£35
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Great Barrington : 415 Stockbridge Rd.
+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 complimentary breakfast
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From£67
Very good 4.0 /5 Recent Reviews 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 ~9.32 miles southeast of Sheffield
  • 3-star property
  • 2 floors in hotel
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From£82
Very good 4.0 /5 Read Reviews Call BookMore Details
Wake Robin Inn
+1-888-897-9207

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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
  • Mid-scale Rural hotel
  • Hotel has 3 meeting rooms
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From£67
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 ~11.57 miles southeast of Sheffield
  • Midscale Rural property
  • 9 sleeping rooms in hotel
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From£180
Very good 4.0 /5 Hotel Reviews Call BookMore Details
The Red Lion Inn in 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 ~12.02 miles north of Sheffield
  • 3 star Rural property
  • Hotel has 8 meeting rooms
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From£60
Average 3.0 /5 Read 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
  • 3 star Mountain property
  • 334 suites in hotel
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From£67
Very good 4.0 /5 Read 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
  • Affordable Resort property
  • Hotel has a green policy Read more
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From£157
Very good 4.0 /5 Hotel 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 +1-888-455-5160 ~12.58 miles northeast of Sheffield
  • Cheap hotel
  • Check-in: 11:00
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From£36
Average 3.0 /5 Hotel Reviews Call BookMore Details
Applegate Inn in 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
  • Midscale Rural property
  • Check-in: 2 pm
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From£120
Very good 4.0 /5 Recent 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 ~14.37 miles northeast of Sheffield
  • 3-star property
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From£60
Average 3.0 /5 Review Score Call BookMore Details
33 Main in Lenox
+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 ~14.49 miles northeast of Sheffield
  • Luxury 5-star property
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From£150
Average 3.0 /5 Recent Reviews Call BookMore Details
Chambery Inn - 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 +1-888-878-9982 ~14.69 miles north of Sheffield
  • 3 star property
  • Check in time: 14:00
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From£67
Very good 4.5 /5 Reviews Call BookMore Details
Pleasant Valley Motel 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 +1-888-389-4485 ~14.83 miles north of Sheffield
  • Two-star hotel
  • Hotel has 16 rooms
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From£45
Average 3.0 /5 Guest Reviews Call BookMore Details
Rodeway Inn
+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 property
  • Hotel has 23 rooms
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From£45
Average 3.0 /5 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 +1-888-675-2083 ~15.35 miles north of Sheffield
  • Affordable Lake property
  • Check in: 3:00 PM
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From£48
Very good 4.0 /5 Review Score 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 ~15.36 miles north of Sheffield
  • Mid-scale Lake property
  • Free complimentary breakfast
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From£45
Very good 4.0 /5 Guest 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
  • Expensive Resort property
  • 2 floors in property
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From£138
Very good 4.5 /5 Guest Reviews Call BookMore Details
Wheatleigh in Lenox
+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 ~16.37 miles north of Sheffield
  • Three Star property
  • Comp. Breakfast
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From£301
Very good 4.0 /5 Review Score 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
  • Affordable hotel
  • Hotel has 2 floors
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From£67
Average 3.0 /5 Recent 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 ~16.91 miles north of Sheffield
  • 4-star Mountain hotel
  • 3 suites in hotel
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From£75
Average 3.0 /5 Recent 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 ~17.06 miles north of Sheffield
  • Four star Rural property
  • Free breakfast
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From£90
Very good 4.0 /5 Latest Reviews Call BookMore Details
Kemble Inn : 2 Kemble St.
+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
  • Midscale Mountain property
  • Check in: 3:00 PM
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From£199
Very good 4.0 /5 Review Score Call BookMore Details
The Constance by The Lenox Collection in 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
  • 4-star property
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From£169
Average 3.0 /5 Guest 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
  • 3-star hotel
  • Check in time: 14:00
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From£150
Average 3.0 /5 Guest Reviews Call BookMore Details
The Dewey by The Lenox Collection - 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
  • Four star property
  • Hotel has 2 floors
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From£56
Average 3.0 /5 Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires - 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
  • 3-star Mountain hotel
  • 28 rooms in property
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From£45
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
  • Expensive Mountain hotel
  • Hotel has 2 floors
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From£82
Average 3.5 /5 Read 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
  • Cheap Suburban hotel
  • Check in time: 2pm
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From£36
Average 3.0 /5 Latest 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
  • Low priced Resort property
  • Comp. Breakfast
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From£48
Average 3.0 /5 Read Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only - 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
  • High end Resort hotel
  • Check-in time: 3PM
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From£103
Average 3.0 /5 Read 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
  • Hotel has 2 floors
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From£188
Very good 4.0 /5 Recent 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
  • Mid-scale Rural hotel
  • Hotel has 3 meeting rooms
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From£112
Very good 4.5 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-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
  • 3-star Mountain hotel
  • 79 sleeping rooms in hotel
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From£82
Average 3.0 /5 Review Score 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
  • Inexpensive hotel
  • Hotel has 96 rooms
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From£109
Very good 4.0 /5 Recent 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
  • Economical Downtown hotel
  • 16 rooms in hotel
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From£27
Poor 2.0 /5 Guest Reviews Call BookMore Details
Lenox Inn - 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-priced property
  • 18 rooms in property
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From£45
Poor 2.0 /5 Review Score 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
  • Affordable Suburban hotel
  • Fitness + Health Center
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From£71
Very good 4.0 /5 Reviews Call BookMore Details
Berkshire Mountain Lodge
+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
  • Low priced Mountain property
  • 2 meeting rooms in hotel
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From£94
Very good 4.5 /5 Read Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites in Pittsfield
+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
  • Three Star Rural hotel
  • 19 suites in hotel
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From£64
Very good 4.5 /5 Read Reviews Call BookMore Details
Americas Best Value Inn Torrington CT : 395 Winsted Rd.
+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
  • 2 floors in property
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From£42
Poor 2.0 /5 Recent Reviews Call BookMore Details
Berkshire Inn
+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
  • Two star Downtown property
  • 36 rooms in property
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From£67
Average 3.0 /5 Recent 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
  • Cheap Downtown hotel
  • 6 suites in hotel
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From£60
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG
+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 hotel
  • Check in: 3:00 PM
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From£60
Average 3.0 /5 Guest Reviews Call BookMore Details
Hudson Whaler : 542 Warren St.
+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
  • Fitness / Gym is on-site
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From£56
Very good 4.0 /5 Recent Reviews Call BookMore Details
Hotel on North in Pittsfield
+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
  • 4 star Downtown property
  • 6 suites in property
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From£112
Excellent 5.0 /5 Review Score Call BookMore Details
The Nest Hudson Hotel in Hudson
+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 hotel
  • Check-in time: 3:00
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From£150
Very good 4.5 /5 Reviews Call BookMore Details

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