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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

Race Brook Lodge - Sheffield
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
864 South Undermountain Rd., Sheffield, MA 01257
  • Mid-scale hotel
  • Hotel has 3 suites
More Photoshotel room
From$90
Average 3.0 /5Reviews CallBookMore Details
Windflower Inn : 684 South Egremont Rd.
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
684 South Egremont Rd., Great Barrington, MA 01230 ~4.60 miles northwest of Sheffield
  • 3-star Mountain hotel
  • 2 meeting rooms in property
More PhotosExterior of Windflower Inn
From$185
Excellent 5.0 /5Read Reviews CallBookMore Details
Days Inn by Wyndham Great Barrington in Great Barrington
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
372 Main St., Great Barrington, MA 01230 ~5.62 miles north of Sheffield
  • Two star Rural hotel
  • 63 sleeping rooms in hotel
More PhotosPhoto of Days Inn by Wyndham Great Barrington
From$100
Very Good 4.0 /5Reviews CallBookMore Details
Fairfield Inn by Marriott
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
249 Stockbridge Rd., Great Barrington, MA 01230 ~6.70 miles north of Sheffield
  • Mid-scale Resort hotel
  • Gym / Fitness Center Available
More PhotosImage of Fairfield Inn by Marriott
From$109
Very Good 4.5 /5Read Reviews CallBookMore Details
Travelodge Great Barrington Berkshires 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
400 Stockbridge Rd., Great Barrington, MA 01230 ~7.04 miles north of Sheffield
  • Low priced Resort hotel
  • Check-in time: 11:00 AM
More PhotosExterior of Travelodge Great Barrington Berkshires
From$47
Average 3.5 /5Hotel Reviews CallBookMore Details
Holiday Inn Express Great Barrington : 415 Stockbridge Rd.
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
415 Stockbridge Rd., Great Barrington, MA 01230 ~7.09 miles north of Sheffield
  • 3-star Mountain hotel
  • 2 floors in hotel
More PhotosPhoto of Holiday Inn Express Great Barrington
From$80
Average 3.0 /5Reviews CallBookMore Details
Blackberry River Inn in Norfolk
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
538 Greenwoods Rd. West, Norfolk, CT 06058 ~9.32 miles southeast of Sheffield
  • Midscale property
  • Check in: 15:00
More PhotosImage of Blackberry River Inn
From$109
Very Good 4.0 /5Hotel Reviews CallBookMore Details
Wake Robin Inn - Lakeville
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
106 Sharon Rd., Lakeville, CT 06039 ~11.32 miles southwest of Sheffield
  • Midscale Rural hotel
  • Free complimentary breakfast
More PhotosPhoto of Wake Robin Inn
From$89
Average 3.0 /5Recent Reviews CallBookMore Details
Manor House Inn : 69 Maple Ave.
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
69 Maple Ave., Norfolk, CT 06058 ~11.57 miles southeast of Sheffield
  • 3-star Rural property
  • 9 rooms in property
More PhotosExterior of Manor House Inn
From$240
Very Good 4.5 /5Latest Reviews CallBookMore Details
The Red Lion Inn
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
30 Main St., Stockbridge, MA 01262 ~12.05 miles north of Sheffield
  • Three Star Rural property
  • Check-in: 3:00
  • Clean rooms
  • Comfortable
More PhotosPhoto of The Red Lion Inn
From$229
Very Good 4.0 /5Latest Reviews CallBookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort - South Lee
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
190 Meadow St., South Lee, MA 01260 ~12.06 miles north of Sheffield
  • Three Star hotel
  • 334 rooms in property
More PhotosImage of Holiday Inn Club Vacations Oak N Spruce Resort
From$80
Average 3.0 /5Read Reviews CallBookMore Details
Interlaken Inn Resort & Conference Center - Lakeville
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
74 Interlaken Rd., Lakeville, CT 06039 ~12.19 miles southwest of Sheffield
  • 3 star Resort hotel
  • 8 suites in hotel
  • Vibe was good
  • Room is all right
More PhotosImage of Interlaken Inn Resort & Conference Center
From$209
Very Good 4.0 /5Reviews CallBookMore Details
Econo Lodge Lee Great Barrington in Lee
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
980 Pleasant St., Lee, MA 01238 ~12.58 miles northeast of Sheffield
  • 2 star hotel
  • Free breakfast available
More PhotosPhoto of Econo Lodge Lee Great Barrington
From$48
Average 3.0 /5Latest Reviews CallBookMore Details
More Homes & Apts at Booking.com

Book online or call +1-800-760-7718

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Applegate 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
279 West Park St., Lee, MA 01238 ~14.31 miles northeast of Sheffield
  • Mid-scale Rural property
  • Free complimentary breakfast
  • Great location
  • Popular among couples
More PhotosImage of Applegate Inn
From$160
Average 3.0 /5Review Score CallBookMore Details
Super 8 Lee / Berkshires / Outlet Area in Lee
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
170 Housatonic St., Lee, MA 01238 ~14.35 miles northeast of Sheffield
  • Low priced hotel
  • Check-in: 11:00 AM
More PhotosImage of Super 8 Lee / Berkshires / Outlet Area
From$47
Average 3.5 /5Guest Reviews CallBookMore Details
33 Main
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
33 Main St., Lenox, MA 01238 ~14.49 miles northeast of Sheffield
  • Luxury Five Star hotel
More Photoshotel room
From$200
Average 3.0 /5Read Reviews CallBookMore Details
Chambery Inn in Lee
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
199 Main St., Lee, 01238 ~14.69 miles north of Sheffield
  • 3-star hotel
  • 9 rooms in property
More PhotosExterior of Chambery Inn
From$90
Very Good 4.5 /5Reviews CallBookMore Details
Pleasant Valley Motel West Stockbridge
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
42 Stockbridge Rd., West Stockbridge, MA 01266 ~14.83 miles north of Sheffield
  • Two-star hotel
  • 16 rooms in hotel
More PhotosPhoto of Pleasant Valley Motel West Stockbridge
From$60
Average 3.0 /5Guest Reviews CallBookMore Details
Rodeway Inn
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
200 Laurel St., Lee, MA 01238 ~15.07 miles north of Sheffield
  • Low Cost hotel
  • Check in: 11:00
More PhotosExterior of Rodeway Inn
From$60
Average 3.0 /5Recent Reviews CallBookMore Details
The Black Swan Inn 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 ~15.36 miles north of Sheffield
  • 3 star Lake hotel
  • Fitness center on property
More PhotosExterior of The Black Swan Inn An Ascend Hotel
From$60
Very Good 4.0 /5Recent Reviews CallBookMore 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 ~16.00 miles north of Sheffield
  • 4-star Resort hotel
  • 57 rooms in property
More PhotosImage of Seven Hills Inn
From$184
Very Good 4.5 /5Latest Reviews CallBookMore Details
Blantyre : 16 Blantyre Rd. Po Box 995
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
16 Blantyre Rd. Po Box 995, Lenox, MA 01240 ~16.36 miles north of Sheffield
  • Three Star hotel
  • Hotel has 24 rooms
More Photoshotel room
From$90
Average 3.0 /5Guest Reviews CallBookMore Details
Wheatleigh : 11 Hawthorne Rd.
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
11 Hawthorne Rd., Lenox, MA 01240 ~16.37 miles north of Sheffield
  • Midscale property
  • Complimentary breakfast is offered
More PhotosPhoto of Wheatleigh
From$90
Average 3.0 /5Reviews CallBookMore Details
Canyon Ranch Lenox - Lenox
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
165 Kemble St., Lenox, MA 01240 ~16.61 miles north of Sheffield
  • 3-star hotel
  • 2 floors in property
More PhotosImage of Canyon Ranch Lenox
From$90
Average 3.0 /5Reviews CallBookMore Details
Apple Tree 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
10 Richmond Mountain Rd., Lenox, MA 01240 ~16.82 miles north of Sheffield
  • 3 star Mountain property
  • Free breakfast available
More PhotosExterior of Apple Tree Inn
From$100
Average 3.0 /5Hotel Reviews CallBookMore Details
Next 25 Sheffield Hotels >  [1 - 25 of 50]    
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Graph: Upcoming 20 Days of Sheffield Hotel Rates

Rates shown are nightly rates before taxes and do not necessarily reflect all Sheffield, MA discounts available. The chart reflects the cheapest Sheffield hotel for each day and each star rating category.

FAQs about hotels in Sheffield

What are the most favored hotels in Sheffield?

Windflower Inn, Hotel on North and Fairfield Inn by Marriott are the best rated hotels based on customer reviews in the last 365 days.

What are the most high-end hotels in Sheffield?

33 Main, Seven Hills Inn and Brook Farm Inn are the top 3 luxury hotels near Sheffield city center.

What hotels are closest to the city center of Sheffield?

Race Brook Lodge, Windflower Inn, and Days Inn by Wyndham Great Barrington are the properties closest to Sheffield city center.

What are the best independent hotels in Sheffield?

Windflower Inn, Hotel on North and Manor House Inn are the best rated independent hotels (not part of a big brand).

What are the most popular Choice Hotels branded hotels in Sheffield?

The Black Swan Inn An Ascend Hotel, Econo Lodge Lee Great Barrington and Rodeway Inn are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the most popular IHG hotels in Sheffield?

Crowne Plaza Pittsfield Berkshires, Holiday Inn Express Great Barrington and Holiday Inn Club Vacations Oak N Spruce Resort are the best rated Intercontinental Hotel Group (IHG) branded hotels (based on user reviews score).

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