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 - Great Barrington
+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
  • Three Star Mountain hotel
  • 13 rooms in hotel
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From$185
Excellent 5.0 /5 Review Score Call BookMore Details
Quality Inn : 372 Main St.
+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
  • Low-priced Rural hotel
  • 2 floors in hotel
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From$100
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
  • Mid-scale Resort hotel
  • Hotel has 5 suites
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From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires : 400 Stockbridge Rd.
+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
  • Low priced Resort hotel
  • Free breakfast
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From$47
Average 3.0 /5 Read 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
  • 3-star Mountain property
  • Access to gym on-site
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From$89
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Blackberry River Inn : 538 Greenwoods Rd. West
+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
  • Three Star property
  • 17 rooms in hotel
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From$109
Very Good 4.0 /5 Review Score 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 hotel
  • Check in: 3 pm
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From$89
Average 3.0 /5 Read Reviews Call BookMore Details
Manor House Inn - Norfolk
+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 hotel
  • 3 floors in hotel
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From$240
Very Good 4.0 /5 Recent 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 ~12.02 miles north of Sheffield
  • Affordable Rural property
  • Check-in time: 3:00
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From$80
Average 3.0 /5 Latest 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 ~12.06 miles north of Sheffield
  • 3-star Mountain property
  • Hotel has a green policy See more
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From$89
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
  • 3-star Resort hotel
  • Hotel has 4 meeting rooms
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From$209
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
  • Economy hotel
  • Hotel has 28 rooms
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From$48
Average 3.0 /5 Review Score Call BookMore Details
Applegate Inn : 279 West Park St.
+1-888-965-8297

How should we direct your call?

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 hotel
  • 11 sleeping rooms in hotel
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From$160
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Pilgrim Inn
+1-888-906-6358

How should we direct your call?

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 property
  • Check-in: 3:00 PM
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
33 Main
+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
  • Luxurious 5 Star hotel
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From$200
Average 3.0 /5 Recent Reviews Call BookMore Details
Chambery Inn in 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$90
Very Good 4.5 /5 Latest 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 hotel
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From$60
Average 3.0 /5 Review Score 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
  • Cheap property
  • Check-in: 11:00
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From$60
Average 3.0 /5 Latest 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
  • Three Star Lake hotel
  • Access to gym on-site
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From$65
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel : 435 Laurel St.
+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 hotel
  • Check-in time: 3:00PM
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From$60
Very Good 4.0 /5 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
  • Four-star Resort hotel
  • Hotel has 2 floors
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From$184
Very Good 4.5 /5 Hotel 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
  • 3 star hotel
  • 2 floors in hotel
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From$400
Very Good 4.0 /5 Hotel 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
  • 3-star property
  • Fitness center on property
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From$90
Average 3.0 /5 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
  • 6 conference rooms in property
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From$100
Average 3.0 /5 Guest Reviews Call BookMore Details
Brook Farm Inn
+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
  • 4-star Rural hotel
  • Has environment-friendly policy See more
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From$120
Very Good 4.0 /5 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 ~17.26 miles north of Sheffield
  • 3 star Mountain property
  • 3 floors in hotel
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From$265
Very Good 4.0 /5 Recent Reviews 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
  • Expensive hotel
  • Hotel has 24 rooms
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From$225
Average 3.0 /5 Read Reviews Call BookMore Details
The Whitlock by The Lenox Collection - 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
  • Affordable hotel
  • 30 sleeping rooms in hotel
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From$200
Average 3.0 /5 Latest Reviews 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 ~17.83 miles north of Sheffield
  • Four-star property
  • Free breakfast
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From$75
Average 3.0 /5 Latest Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires
+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
  • Hotel has 28 rooms
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From$60
Very Good 4.0 /5 Latest 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 ~18.62 miles north of Sheffield
  • High-end Mountain property
  • 2 floors in property
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From$109
Average 3.5 /5 Recent Reviews Call BookMore Details
Life House Berkshires
+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
  • Inexpensive Suburban hotel
  • Check-in time: 2pm
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From$49
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
  • Low Cost Resort property
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From$65
Average 3.0 /5 Review Score 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
  • Four star Resort hotel
  • Fitness center on property
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From$138
Average 3.0 /5 Review Score Call BookMore Details
The Amselhaus
+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: 0:00 pm
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From$250
Very Good 4.0 /5 Read 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
  • 3-star Rural property
  • 4 suites in property
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From$150
Very Good 4.5 /5 Hotel 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
  • 3 star Mountain property
  • Hotel has 3 floors
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From$109
Average 3.0 /5 Hotel Reviews Call BookMore Details
Yankee Inn : 461 Pittsfield Rd.
+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
  • Cheap property
  • 3 floors in hotel
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From$145
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Knights Inn 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
  • Check in: 2.00 pm
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From$37
Poor 2.0 /5 Guest 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
  • Two star hotel
  • Check-in: 15:00
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From$60
Poor 2.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Lenox Pittsfield - 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
  • Midscale Suburban hotel
  • Fitness center on property
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From$95
Very Good 4.0 /5 Review Score 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
  • 2 star Mountain property
  • Fitness center on property
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From$125
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
  • 3-star Rural hotel
  • Fitness + Health Center
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From$79
Very Good 4.0 /5 Hotel 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 hotel
  • Check in: 3:00pm
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From$57
Poor 2.0 /5 Recent Reviews Call BookMore Details
Berkshire Inn : 150 West Housatonic St.
+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
  • Free complimentary breakfast
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From$90
Average 3.0 /5 Guest Reviews Call BookMore Details
St. Charles Hotel - 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
  • Low-priced Downtown hotel
  • Hotel has 3 floors
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From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG in Pittsfield
+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
  • Midscale Downtown hotel
  • Access to gym on-site
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From$80
Average 3.0 /5 Guest 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
  • Mid-scale Downtown property
  • Gym is available on property
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From$75
Very Good 4.0 /5 Recent 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
  • 4 star Downtown hotel
  • Has environment-friendly policy Read more
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From$150
Excellent 5.0 /5 Latest Reviews Call BookMore Details
The Nest Hudson Hotel - 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
  • High-end Downtown hotel
  • 6 rooms in property
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From$200
Very Good 4.5 /5 Recent Reviews Call BookMore Details

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