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 : 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
  • Three Star Mountain property
  • Hotel has 2 floors
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From$185
Excellent 5.0 /5 Reviews 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
  • 2 star Rural hotel
  • Access to gym on-site
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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 : 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 ~6.70 miles north of Sheffield
  • Three Star Resort property
  • 60 sleeping rooms in hotel
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From$109
Very good 4.0 /5 Guest 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 ~7.04 miles north of Sheffield
  • Low priced Resort hotel
  • Check in: 11:00 AM
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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
  • Affordable Mountain property
  • Check in: 3:00pm
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From$89
Very good 4.0 /5 Recent Reviews Call BookMore Details
Blackberry River Inn in Norfolk
+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
  • 3 star hotel
  • Hotel has 2 floors
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From$109
Very good 4.0 /5 Hotel 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 ~11.32 miles southwest of Sheffield
  • Midscale Rural hotel
  • Hotel has 3 meeting rooms
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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
  • Three Star Rural hotel
  • Free breakfast
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From$240
Very good 4.0 /5 Recent Reviews Call BookMore Details
The Red Lion Inn - Stockbridge
+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
  • Midscale Rural hotel
  • 125 rooms in hotel
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From$80
Average 3.0 /5 Recent 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 ~12.06 miles north of Sheffield
  • Affordable Mountain hotel
  • 334 sleeping rooms in hotel
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From$89
Very good 4.0 /5 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
  • 3 star Resort hotel
  • 8 suites in property
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From$209
Very good 4.0 /5 Latest 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
  • Check in time: 11:00
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From$48
Average 3.0 /5 Guest 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
  • Free breakfast
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From$160
Very good 4.0 /5 Guest Reviews Call BookMore Details
Pilgrim Inn in Lee
+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 hotel
  • Check in: 3:00 PM
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
33 Main : 33 Main St.
+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$200
Average 3.0 /5 Guest Reviews 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
  • Mid-scale property
  • 9 rooms in hotel
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From$90
Very good 4.5 /5 Review Score 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 ~14.83 miles north of Sheffield
  • Cheap property
  • 16 rooms in property
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From$60
Average 3.0 /5 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
  • Economy hotel
  • Check in: 11:00
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From$60
Average 3.0 /5 Guest 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
  • Three Star Lake property
  • 52 rooms in property
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From$65
Very good 4.0 /5 Latest 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
  • 3 star Lake property
  • Gym is available on property
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From$60
Very good 4.0 /5 Recent 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 ~16.00 miles north of Sheffield
  • 4-star Resort property
  • Hotel has 4 suites
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From$184
Very good 4.5 /5 Guest 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 property
  • Check-in: 16:00
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From$400
Very good 4.0 /5 Guest 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
  • 102 rooms in hotel
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From$90
Average 3.0 /5 Review Score Call BookMore Details
Apple Tree Inn : 10 Richmond Mountain Rd.
+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
  • High end Mountain hotel
  • 34 rooms in property
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From$100
Average 3.0 /5 Read Reviews Call BookMore Details
Brook Farm Inn in 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
  • High end Rural property
  • Check-in: 3 pm
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From$120
Very good 4.0 /5 Hotel 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
  • Mid-scale Mountain property
  • Hotel has a green policy See more
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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 ~17.31 miles north of Sheffield
  • Expensive hotel
  • Comp. Breakfast
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From$225
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
  • Three Star hotel
  • Check-in: 14:00
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From$200
Average 3.0 /5 Latest 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 ~17.83 miles north of Sheffield
  • Four-star hotel
  • Free breakfast available
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From$75
Average 3.0 /5 Recent Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires : 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
  • Mid-scale Mountain property
  • 3 suites in property
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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
  • Expensive Mountain property
  • 90 rooms in hotel
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From$109
Average 3.5 /5 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
  • Inexpensive Suburban hotel
  • Check in time: 2pm
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From$49
Average 3.0 /5 Latest Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox : 462 Pittsfield Rd.
+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
  • Two star Resort property
  • Free breakfast
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From$65
Average 3.0 /5 Read Reviews Call BookMore Details
Miraval Berkshires Resort & Spa - All Inclusive Adults Only : 55 Lee Rd.
+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
  • Expensive Resort property
  • Has environment-friendly policy See policy
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From$138
Average 3.0 /5 Latest Reviews 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 : 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
  • 3 star Rural property
  • Free complimentary breakfast
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From$150
Very good 4.5 /5 Review Score Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox : 445 Pittsfield Rd.
+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
  • Gym is available on property
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From$109
Average 3.0 /5 Read 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
  • Two-star property
  • Hotel has 9 suites
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From$145
Very good 4.0 /5 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 priced Downtown hotel
  • 16 sleeping rooms in hotel
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From$37
Poor 2.0 /5 Latest 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
  • 2-star hotel
  • 18 rooms in hotel
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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
  • Midscale Suburban property
  • Hotel has 2 meeting rooms
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From$95
Very good 4.0 /5 Guest Reviews Call BookMore Details
Berkshire Mountain Lodge : 8 Dan Fox Dr.
+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 Mountain hotel
  • Hotel has 5 floors
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From$125
Very good 4.5 /5 Review Score Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites
+1-888-469-4795

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
  • Mid-scale Rural hotel
  • Check-in: 03:00
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From$85
Very good 4.5 /5 Hotel Reviews Call BookMore Details
Americas Best Value Inn Torrington CT - Torrington
+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 hotel
  • 30 suites in property
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From$57
Poor 2.0 /5 Review Score 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
  • Low priced Downtown hotel
  • Hotel has 2 floors
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From$90
Average 3.0 /5 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
  • Economical Downtown property
  • Check in time: 4:00 PM
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From$80
Average 3.0 /5 Latest Reviews 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
  • Mid-scale Downtown hotel
  • Check in: 3:00 PM
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Hudson Whaler
+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
  • 3 floors in property
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From$75
Very good 4.0 /5 Read 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
  • 4 floors in property
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From$150
Excellent 5.0 /5 Guest Reviews Call BookMore Details
The Nest Hudson Hotel
+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
  • Four star Downtown property
  • 6 rooms in property
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From$200
Very good 4.5 /5 Read Reviews Call BookMore Details

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