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 - 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
  • Check in: 2:00PM
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From$185
Excellent 5.0 /5 Read Reviews Call BookMore Details
Quality Inn in 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 ~5.62 miles north of Sheffield
  • Cheap Rural hotel
  • 2 floors in hotel
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From$100
Very Good 4.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi - 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
  • 3-star Resort property
  • Hotel has 3 floors
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From$109
Very Good 4.0 /5 Review Score Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires
+1-800-805-5223

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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
  • Two-star Resort property
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From$47
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel - Great Barrington
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
415 Stockbridge Road41, Great Barrington, MA 01230 +1-888-965-1860 ~7.10 miles north of Sheffield
  • Affordable Mountain property
  • Fitness + Health Center
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From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Blackberry River Inn
+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
  • Mid-scale property
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From$109
Very Good 4.0 /5 Hotel 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
  • Affordable Rural property
  • Hotel has a green policy Read more
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From$89
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
  • 3 star Rural hotel
  • Free breakfast available
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From$240
Very Good 4.0 /5 Latest Reviews Call BookMore Details
The Red Lion Inn
+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 hotel
  • 8 meeting rooms in hotel
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From$80
Average 3.0 /5 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 hotel
  • Hotel has 334 rooms
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From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Interlaken Inn & Resort
+1-888-841-5292

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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
  • 4 conference rooms in property
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From$209
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington : 980 Pleasant St.
+1-888-455-5160

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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
  • Low priced property
  • Free breakfast available
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From$48
Average 3.0 /5 Guest 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 ~14.31 miles northeast of Sheffield
  • 3-star Rural hotel
  • 3 floors in property
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From$160
Very Good 4.0 /5 Reviews Call BookMore Details
Pilgrim Inn - 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
  • Three Star hotel
  • Check-in time: 3:00 PM
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From$80
Average 3.0 /5 Guest 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
  • Luxury 5-star hotel
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From$200
Average 3.0 /5 Review Score Call BookMore Details
Chambery Inn : 199 Main St.
+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
  • Hotel has 9 rooms
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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

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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 rooms in property
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From$60
Average 3.0 /5 Latest Reviews Call BookMore Details
Rodeway Inn - Lee
+1-888-389-4121

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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
  • 2 star hotel
  • 23 rooms in property
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From$60
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 +1-888-675-2083 ~15.35 miles north of Sheffield
  • Three Star Lake property
  • Check-in: 3:00 PM
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From$65
Very Good 4.0 /5 Hotel 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
  • Mid-scale Lake property
  • Complimentary breakfast is offered
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From$60
Very Good 4.0 /5 Read 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
  • Expensive Resort hotel
  • Hotel has 57 rooms
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From$184
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
Wheatleigh
+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
  • Mid-scale hotel
  • Free breakfast available
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From$400
Very Good 4.0 /5 Reviews Call BookMore Details
Canyon Ranch Lenox - 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
  • Midscale property
  • Access to gym on-site
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From$90
Average 3.0 /5 Guest 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
  • 4-star Mountain property
  • Check in: 4:00 PM
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From$100
Average 3.0 /5 Read 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
  • Four-star Rural hotel
  • Free complimentary breakfast
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From$120
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 ~17.26 miles north of Sheffield
  • 3-star Mountain property
  • 12 rooms in property
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From$265
Very Good 4.0 /5 Read Reviews Call BookMore Details
The Constance by The Lenox Collection : 11 Old Stockbridge Rd.
+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 hotel
  • Comp. Breakfast
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From$225
Average 3.0 /5 Hotel 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
  • Mid-scale property
  • Hotel has 30 rooms
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From$200
Average 3.0 /5 Latest 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
  • High end hotel
  • 2 floors in hotel
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From$75
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Cornell Inn, Lenox : 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 ~18.06 miles north of Sheffield
  • 3 star Mountain hotel
  • 3 suites in property
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From$60
Very Good 4.0 /5 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 hotel
  • 2 floors in hotel
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From$109
Average 3.5 /5 Reviews Call BookMore Details
Life House Berkshires : 194 Pittsfield Rd.
+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$49
Average 3.0 /5 Hotel 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
  • 2 star Resort hotel
  • Hotel has 2 floors
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From$65
Average 3.0 /5 Latest 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
  • 4 star Resort hotel
  • 19 suites in hotel
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From$138
Average 3.0 /5 Hotel 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
  • High end Riverfront hotel
  • Free comp. breakfast
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From$250
Very Good 4.0 /5 Hotel 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
  • Midscale Rural hotel
  • Comp. Breakfast
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From$150
Very Good 4.5 /5 Review Score 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
  • Mid-scale Mountain hotel
  • 24 suites in property
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From$109
Average 3.0 /5 Latest 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 property
  • Comp. Breakfast
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From$145
Very Good 4.0 /5 Read 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
  • Low Cost Downtown property
  • 16 sleeping rooms in hotel
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From$37
Poor 2.0 /5 Review Score Call BookMore Details
Lenox Inn
+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 hotel
  • Check-in: 15:00
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From$60
Poor 2.0 /5 Read 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
  • 3-star Suburban hotel
  • Check in time: 03:00PM
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From$95
Very Good 4.0 /5 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
  • Economy property
  • Hotel has 146 suites
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From$125
Very Good 4.5 /5 Review Score Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites - 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
  • 3 star Rural property
  • Gym / Fitness Center Available
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From$79
Very Good 4.0 /5 Guest 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
  • Two-star Suburban property
  • 91 rooms in hotel
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From$57
Poor 2.0 /5 Review Score 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
  • Low Cost Downtown property
  • Comp. Breakfast
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From$90
Average 3.0 /5 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
  • 2 star Downtown hotel
  • Hotel has 3 floors
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From$80
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
+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
  • Three Star Downtown property
  • 26 suites in hotel
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From$80
Average 3.0 /5 Latest 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
  • Fitness + Health Center
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From$75
Very Good 4.0 /5 Reviews Call BookMore Details
Hotel on North : 297 North St.
+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
  • 4 floors in property
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From$150
Excellent 5.0 /5 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 property
  • Hotel has 6 suites
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From$200
Very Good 4.5 /5 Read Reviews Call BookMore Details

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