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
+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 ~4.59 miles northwest of Sheffield
  • Affordable Mountain hotel
  • 13 rooms in property
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From$185
Excellent 5.0 /5 Reviews Call BookMore Details
Quality Inn Great Barrington in Great Barrington
+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 ~5.61 miles north of Sheffield
  • 2 star Rural property
  • Access to gym on-site
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From$100
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi : 249 Stockbridge Rd.
+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 ~6.69 miles north of Sheffield
  • Midscale Resort property
  • Free comp. breakfast
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From$109
Very good 4.0 /5 Read Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires
+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 ~7.03 miles north of Sheffield
  • Low-priced Resort property
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From$47
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Great Barrington in 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 ~7.13 miles north of Sheffield
  • 3 star Mountain hotel
  • 78 rooms in property
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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

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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 ~9.30 miles southeast of Sheffield
  • Mid-scale property
  • 17 rooms in property
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From$109
Very good 4.0 /5 Reviews Call BookMore Details
Wake Robin Inn
+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 ~11.30 miles southwest of Sheffield
  • Affordable Rural hotel
  • Hotel has 38 rooms
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From$89
Average 3.0 /5 Review Score 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 ~11.55 miles southeast of Sheffield
  • Three Star Rural property
  • 9 rooms in property
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From$240
Very good 4.0 /5 Recent 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 ~12.00 miles north of Sheffield
  • 3-star Rural property
  • 8 meeting rooms in hotel
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From$80
Average 3.0 /5 Guest Reviews 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 ~12.04 miles north of Sheffield
  • Mid-scale Mountain property
  • Hotel has an eco-friendly policy Read more
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From$89
Very good 4.0 /5 Latest Reviews Call BookMore Details
Interlaken Inn
+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 ~12.21 miles southwest of Sheffield
  • 3 star Resort hotel
  • Hotel has an eco-friendly policy See more
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From$179
Very good 4.0 /5 Read Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington in Lee
+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 ~12.56 miles northeast of Sheffield
  • 2 star hotel
  • Check-in time: 11:00
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From$48
Average 3.0 /5 Latest 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 ~14.29 miles northeast of Sheffield
  • Three Star Rural hotel
  • Check in time: 2 pm
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From$160
Very good 4.0 /5 Read 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 ~14.36 miles northeast of Sheffield
  • 3 star property
  • Check in time: 3:00 PM
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From$80
Average 3.0 /5 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 ~14.47 miles northeast of Sheffield
  • Luxurious 5-star property
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From$200
Average 3.0 /5 Review Score 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 ~14.67 miles north of Sheffield
  • Mid-scale hotel
  • Check in time: 14:00
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From$90
Very good 4.5 /5 Recent Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge - 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 ~14.80 miles north of Sheffield
  • 2 star property
  • Check in time: 13:00
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From$60
Average 3.0 /5 Recent 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 ~15.05 miles north of Sheffield
  • Two star hotel
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From$60
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 ~15.33 miles north of Sheffield
  • 3 star Lake property
  • Fitness + Health Center
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From$65
Very good 4.0 /5 Guest Reviews 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 ~15.35 miles north of Sheffield
  • Mid-scale Lake property
  • Check in time: 3:00PM
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From$60
Very good 4.0 /5 Guest Reviews Call BookMore Details
Seven Hills Inn - 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 ~15.98 miles north of Sheffield
  • High-end Resort hotel
  • 57 rooms in hotel
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From$184
Very good 4.5 /5 Review Score Call BookMore Details
Wheatleigh - Lenox
+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 ~16.35 miles north of Sheffield
  • Mid-scale property
  • Check in: 16:00
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From$400
Very good 4.0 /5 Read Reviews 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 ~16.59 miles north of Sheffield
  • Affordable hotel
  • 102 rooms in property
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From$90
Average 3.0 /5 Read 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 ~16.89 miles north of Sheffield
  • Four-star Mountain hotel
  • Check in: 4:00 PM
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From$100
Average 3.0 /5 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 ~17.04 miles north of Sheffield
  • Expensive Rural property
  • Check-in: 3 pm
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From$120
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 ~17.24 miles north of Sheffield
  • 3 star Mountain property
  • Check in time: 3:00 PM
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From$265
Very good 4.0 /5 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 ~17.29 miles north of Sheffield
  • Four star property
  • Hotel has 24 rooms
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From$225
Average 3.0 /5 Guest Reviews Call BookMore Details
The Whitlock by The Lenox Collection in 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 ~17.36 miles north of Sheffield
  • 3 star property
  • 2 floors in property
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From$200
Average 3.0 /5 Recent 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 ~17.80 miles north of Sheffield
  • High-end hotel
  • Free comp. breakfast
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From$75
Average 3.0 /5 Read 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 ~18.03 miles north of Sheffield
  • 3 star Mountain hotel
  • 2 floors in property
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From$60
Very good 4.0 /5 Latest 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 ~18.59 miles north of Sheffield
  • 4-star Mountain hotel
  • Hotel has an eco-friendly policy Learn more
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From$109
Average 3.5 /5 Review Score Call BookMore Details
Element Lenox Berkshires - Lenox
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
130 Pittsfield Rd., Lenox, MA 01240 +1-888-749-6785 ~19.15 miles north of Sheffield
  • Three Star Mountain hotel
  • Check in time: 3:00PM
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From$50
Average 3.0 /5 Latest Reviews Call BookMore Details
Life House Berkshires
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
194 Pittsfield Rd., Lenox, MA 01240 +1-888-878-9982 ~19.47 miles north of Sheffield
  • Cheap Suburban property
  • Check-in: 2pm
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From$49
Average 3.0 /5 Review Score Call BookMore Details
Howard Johnson by Wyndham Lenox : 462 Pittsfield Rd.
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
462 Pittsfield Rd., Lenox, MA 01240 +1-888-389-4485 ~19.67 miles north of Sheffield
  • 2-star Resort hotel
  • 44 rooms in hotel
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From$65
Average 3.0 /5 Review Score Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
55 Lee Rd., Lenox, MA 01240 +1-888-389-4121 ~20.19 miles north of Sheffield
  • High end Resort hotel
  • 10 meeting rooms in property
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From$138
Average 3.0 /5 Guest Reviews Call BookMore Details
The Amselhaus : 6 Rug Rd.
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
6 Rug Rd., Cornwall Bridge, CT 06754 +1-888-675-2083 ~20.21 miles south of Sheffield
  • High end Riverfront hotel
  • Complimentary breakfast is offered
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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
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
802 State Rd., Richmond, MA 01254 +1-800-716-8490 ~20.45 miles north of Sheffield
  • Affordable Rural property
  • 3 floors in hotel
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From$150
Very good 4.5 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox : 445 Pittsfield Rd.
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
445 Pittsfield Rd., Lenox, MA 01240 +1-800-805-5223 ~20.64 miles north of Sheffield
  • Midscale Mountain hotel
  • 3 floors in hotel
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From$109
Average 3.0 /5 Recent Reviews Call BookMore Details
The Yankee, Trademark Collection by Wyndham
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
461 Pittsfield Rd., Lenox, MA 01240 +1-888-965-1860 ~20.69 miles north of Sheffield
  • Low priced property
  • Free comp. breakfast
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From$145
Very good 4.0 /5 Guest Reviews Call BookMore Details
Knights Inn Lenox - Lenox
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
474 Pittsfield Rd., Lenox, MA 01240 +1-888-788-5576 ~20.72 miles north of Sheffield
  • Two-star Downtown property
  • Check-in time: 2.00 pm
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From$37
Poor 2.0 /5 Hotel Reviews Call BookMore Details
Lenox Inn - Lenox
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
525 Pittsfield Rd., Lenox, MA 01240 +1-888-897-9207 ~20.96 miles north of Sheffield
  • Cheap property
  • Hotel has 18 rooms
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From$60
Poor 2.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Pittsfield Lenox Berkshires - Pittsfield
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1055 South St., Pittsfield, MA 01201 +1-888-311-4278 ~21.02 miles north of Sheffield
  • 3-star Suburban property
  • Fitness center on property
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield - Pittsfield
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
1032 South St., Pittsfield, MA 01201 +1-888-469-4795 ~21.02 miles north of Sheffield
  • Three Star Suburban hotel
  • 2 conference rooms in property
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From$95
Very good 4.0 /5 Review Score Call BookMore Details
Berkshire Mountain Lodge
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
8 Dan Fox Dr., Pittsfield, MA 01201 +1-888-734-9421 ~21.37 miles north of Sheffield
  • Cheap Mountain property
  • Check-in: 4:00PM
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From$125
Very good 4.5 /5 Review Score Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
1350 West Housatonic St., Pittsfield, MA 01201 +1-888-841-5292 ~22.43 miles north of Sheffield
  • Three Star Rural hotel
  • Hotel has 3 floors
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From$85
Very good 4.5 /5 Recent Reviews Call BookMore Details
Americas Best Value Inn Torrington CT in Torrington
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
395 Winsted Rd., Torrington, CT 06790 +1-888-455-5160 ~23.28 miles southeast of Sheffield
  • 2-star Suburban hotel
  • Fitness + Health Center
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From$57
Poor 2.0 /5 Read Reviews Call BookMore Details
Berkshire Inn : 150 West Housatonic St.
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
150 West Housatonic St., Pittsfield, MA 01201 +1-888-965-8297 ~23.49 miles north of Sheffield
  • Economy Downtown hotel
  • 36 sleeping rooms in hotel
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From$90
Average 3.0 /5 Review Score Call BookMore Details
St. Charles Hotel in Hudson
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
16 Park Place, Hudson, NY 12534 +1-888-906-6358 ~23.77 miles west of Sheffield
  • Low-priced Downtown property
  • Check-in: 4:00 PM
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
1 West St., Pittsfield, MA 01201 +1-888-749-6785 ~23.86 miles north of Sheffield
  • Affordable Downtown hotel
  • 170 rooms in hotel
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Hudson Whaler in Hudson
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
542 Warren St., Hudson, NY 12534 +1-888-878-9982 ~23.92 miles west of Sheffield
  • Affordable Downtown property
  • Fitness + Health Center
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From$75
Very good 4.0 /5 Reviews Call BookMore Details

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