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

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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
  • Mid-scale Mountain hotel
  • Free breakfast
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From$185
Excellent 5.0 /5 Hotel Reviews Call BookMore Details
Quality Inn
+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
  • Two star Rural hotel
  • Hotel has 63 rooms
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From$100
Very Good 4.0 /5 Reviews 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
  • 3 star Resort hotel
  • Free breakfast available
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From$109
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires - Great Barrington
+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
  • Economical Resort hotel
  • Comp. Breakfast
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From$47
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel : 415 Stockbridge Road41
+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
  • 3 star Mountain hotel
  • Hotel has 6 suites
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From$80
Average 3.0 /5 Review Score 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
  • 3-star property
  • 2 floors in property
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From$109
Very Good 4.0 /5 Guest 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
  • Three Star Rural property
  • 38 rooms in hotel
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From$89
Average 3.0 /5 Review Score Call BookMore Details
Manor House Inn - Norfolk
+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
  • Mid-scale Rural property
  • 9 rooms in property
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From$240
Very Good 4.0 /5 Guest 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 ~12.05 miles north of Sheffield
  • Mid-scale Rural hotel
  • Hotel has 35 suites
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From$229
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort
+1-888-734-9421

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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
  • Affordable Mountain property
  • Has environment-friendly policy See more
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From$89
Very Good 4.0 /5 Review Score Call BookMore Details
Interlaken Inn & Resort - Lakeville
+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
  • Three Star Resort hotel
  • 86 rooms in property
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From$209
Very Good 4.0 /5 Read Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington
+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
  • Economical hotel
  • Check in: 11:00
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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
  • Midscale Rural hotel
  • Comp. Breakfast
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From$160
Very Good 4.0 /5 Hotel 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
  • Mid-scale property
  • Check-in: 3:00 PM
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From$80
Average 3.0 /5 Hotel 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 Five Star hotel
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From$200
Average 3.0 /5 Recent 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 property
  • Check in time: 14:00
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From$90
Very Good 4.5 /5 Read Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge
+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
  • Inexpensive property
  • Check-in: 13:00
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From$60
Average 3.0 /5 Recent 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 property
  • 23 rooms in hotel
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From$60
Average 3.0 /5 Review Score 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 Website +1-888-675-2083 ~15.35 miles north of Sheffield
  • Affordable Lake hotel
  • Check in time: 3:00 PM
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From$65
Very Good 4.0 /5 Recent 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
  • 3-star Lake hotel
  • 52 rooms in hotel
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From$60
Very Good 4.0 /5 Review Score 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
  • Four star Resort property
  • Hotel has 57 rooms
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From$184
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
  • Affordable hotel
  • 9 suites in hotel
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From$400
Very Good 4.0 /5 Latest 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
  • Midscale property
  • Check-in: 15:00
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From$90
Average 3.0 /5 Review Score Call BookMore Details
Apple Tree Inn in Lenox
+1-888-897-9207

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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
  • 6 meeting 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
  • High end Rural property
  • 3 floors in hotel
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From$120
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
  • 3-star Mountain hotel
  • 12 sleeping rooms in hotel
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From$265
Very Good 4.0 /5 Reviews Call BookMore Details
The Constance 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
  • High-end property
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From$225
Average 3.0 /5 Recent Reviews Call BookMore Details
The Whitlock
+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 property
  • 32 rooms in property
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From$200
Average 3.0 /5 Latest Reviews Call BookMore Details
The Dewey
+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 hotel
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From$75
Average 3.0 /5 Latest 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
  • Midscale Mountain hotel
  • Check-in: 3:00 PM-8PM
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From$60
Very Good 4.0 /5 Guest 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 a green policy Learn more
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From$109
Average 3.5 /5 Guest 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
  • Two star Suburban property
  • Comp. Breakfast
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From$49
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
  • Economy Resort property
  • Check-in time: 2:00 PM
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From$65
Average 3.0 /5 Hotel 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
  • 4-star Resort hotel
  • 19 suites in hotel
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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
  • High-end Riverfront hotel
  • Free breakfast available
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From$250
Very Good 4.0 /5 Review Score Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center : 802 State Rd.
+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 property
  • 4 suites in hotel
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From$150
Very Good 4.5 /5 Guest Reviews 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
  • Mid-scale Mountain property
  • Comp. Breakfast
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From$109
Average 3.0 /5 Reviews Call BookMore Details
The Yankee, Trademark Collection by Wyndham
+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 property
  • Gym / Fitness Center Available
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From$65
Very Good 4.0 /5 Reviews 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
  • Two star Downtown hotel
  • 16 rooms in property
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From$37
Poor 2.0 /5 Hotel Reviews 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
  • Inexpensive hotel
  • Hotel has 18 rooms
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From$60
Poor 2.0 /5 Hotel 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
  • Mid-scale Suburban hotel
  • Fitness / Gym is on-site
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From$95
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites in Pittsfield
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1350 West Housatonic St., Pittsfield, MA 01201 +1-888-311-4278 ~22.47 miles north of Sheffield
  • Three Star Rural hotel
  • Free breakfast available
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From$79
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Americas Best Value Inn Torrington CT - Torrington
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
395 Winsted Rd., Torrington, CT 06790 +1-888-469-4795 ~23.33 miles southeast of Sheffield
  • 2-star Suburban property
  • Free complimentary breakfast
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From$57
Poor 2.0 /5 Latest Reviews Call BookMore Details
Berkshire Inn
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
150 West Housatonic St., Pittsfield, MA 01201 +1-888-734-9421 ~23.52 miles north of Sheffield
  • Economical Downtown hotel
  • Fitness / Gym is on-site
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From$90
Average 3.0 /5 Hotel Reviews Call BookMore Details
St. Charles Hotel - Hudson
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
16 Park Place, Hudson, NY 12534 +1-888-841-5292 ~23.78 miles west of Sheffield
  • Inexpensive Downtown property
  • 34 rooms in property
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel in Pittsfield
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
1 West St., Pittsfield, MA 01201 +1-888-455-5160 ~23.89 miles north of Sheffield
  • Mid-scale Downtown hotel
  • Gym / Fitness Center Available
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Hudson Whaler in Hudson
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
542 Warren St., Hudson, NY 12534 +1-888-965-8297 ~23.93 miles west of Sheffield
  • Three Star Downtown property
  • Gym is available on property
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From$75
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hotel on North : 297 North St.
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
297 North St., Pittsfield, MA 01201 +1-888-906-6358 ~24.21 miles north of Sheffield
  • 4 star Downtown property
  • 6 suites in hotel
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From$150
Excellent 5.0 /5 Review Score Call BookMore Details
The Nest Hudson Hotel : 330 Union St.
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
330 Union St., Hudson, NY 12534 +1-888-749-6785 ~24.29 miles west of Sheffield
  • 4-star Downtown hotel
  • Check in time: 3:00
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From$200
Very Good 4.5 /5 Read Reviews Call BookMore Details
Days Inn by Wyndham Torrington in Torrington
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
492 East Main St., Torrington, CT 06790 +1-888-878-9982 ~24.50 miles southeast of Sheffield
  • Two-star Mountain hotel
  • Free breakfast
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From$60
Average 3.0 /5 Recent Reviews Call BookMore Details

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