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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

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 ~4.59 miles northwest of Sheffield
  • Mid-scale Mountain hotel
  • Complimentary breakfast is offered
More Photos Image of The Windflower Inn
From£138
Excellent 5.0 /5 Reviews Call BookMore Details
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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 ~5.61 miles north of Sheffield
  • Economical Rural hotel
More Photos Exterior of Quality Inn
From£75
Very good 4.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
+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 ~6.69 miles north of Sheffield
  • Affordable Resort hotel
  • 60 rooms in property
More Photos Image of Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
From£81
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires - Great Barrington
+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 ~7.03 miles north of Sheffield
  • Inexpensive Resort property
  • Check in time: 11:00 AM
More Photos Image of Travelodge by Wyndham Great Barrington Berkshires
From£35
Average 3.0 /5 Guest 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 ~7.13 miles north of Sheffield
  • Affordable Mountain property
  • Hotel has an eco-friendly policy Read more
More Photos Exterior of Holiday Inn Express Great Barrington
From£66
Very good 4.0 /5 Recent Reviews Call BookMore Details
Blackberry River Inn - 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 ~9.30 miles southeast of Sheffield
  • 3-star property
  • 17 sleeping rooms in hotel
More Photos Image of Blackberry River Inn
From£81
Very good 4.0 /5 Read 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 ~11.30 miles southwest of Sheffield
  • Three Star Rural property
  • 3 conference rooms in property
More Photos Exterior of Wake Robin Inn
From£66
Average 3.0 /5 Read Reviews 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 ~11.55 miles southeast of Sheffield
  • Mid-scale Rural hotel
  • 3 floors in property
More Photos Exterior of Manor House Inn
From£180
Very good 4.0 /5 Recent Reviews Call BookMore Details
The Red Lion Inn
+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 ~12.00 miles north of Sheffield
  • Mid-scale Rural property
  • Fitness + Health Center
More Photos Exterior of The Red Lion Inn
From£60
Average 3.0 /5 Hotel 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 ~12.04 miles north of Sheffield
  • 3 star Mountain property
  • 334 rooms in property
More Photos Photo of Holiday Inn Club Vacations Oak N Spruce Resort
From£66
Very good 4.0 /5 Reviews Call BookMore Details
Interlaken Inn in Lakeville
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
74 Interlaken Rd., Lakeville, CT 06039 ~12.21 miles southwest of Sheffield
  • Mid-scale Resort hotel
  • Complimentary breakfast is offered
More Photos Photo of Interlaken Inn
From£134
Very good 4.0 /5 Hotel 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 ~12.56 miles northeast of Sheffield
  • 2-star hotel
  • Hotel has 28 rooms
More Photos Exterior of Econo Lodge Lee - Great Barrington
From£36
Average 3.0 /5 Latest Reviews Call BookMore Details
Applegate Inn : 279 West Park St.
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
279 West Park St., Lee, MA 01238 ~14.29 miles northeast of Sheffield
  • Affordable Rural hotel
  • Hotel has 6 suites
More Photos Image of Applegate Inn
From£120
Very good 4.0 /5 Hotel Reviews Call BookMore Details
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Pilgrim Inn : 165 Housatonic St.
+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 ~14.36 miles northeast of Sheffield
  • Three Star hotel
  • Check in time: 3:00 PM
More Photos Exterior of Pilgrim Inn
From£60
Average 3.0 /5 Latest Reviews Call BookMore Details
33 Main in Lenox
+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 ~14.47 miles northeast of Sheffield
  • Luxury Five Star hotel
More Photos hotel room
From£150
Average 3.0 /5 Recent Reviews Call BookMore Details
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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 ~14.67 miles north of Sheffield
  • 3 star property
  • Hotel has 9 rooms
More Photos Exterior of Chambery Inn
From£67
Very good 4.5 /5 Hotel Reviews Call BookMore Details
Pleasant Valley Motel West Stockbridge in 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 ~14.80 miles north of Sheffield
  • Two star property
  • Hotel has 16 rooms
More Photos Exterior of Pleasant Valley Motel West Stockbridge
From£45
Average 3.0 /5 Guest Reviews Call BookMore Details
Rodeway Inn - Lee
+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 ~15.05 miles north of Sheffield
  • Inexpensive hotel
  • Check in time: 11:00
More Photos Photo of Rodeway Inn
From£45
Average 3.0 /5 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 Website ~15.33 miles north of Sheffield
  • Mid-scale Lake property
  • Fitness + Health Center
More Photos Image of Quality Inn
From£48
Very good 4.0 /5 Read 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 ~15.35 miles north of Sheffield
  • 3 star Lake hotel
  • Gym / Fitness Center Available
More Photos Image of Black Swan Inn Lee Lenox An Ascend Hotel
From£45
Very good 4.0 /5 Read 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 ~15.98 miles north of Sheffield
  • High end Resort hotel
  • 57 rooms in hotel
More Photos Image of Seven Hills Inn
From£138
Very good 4.5 /5 Hotel 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 ~16.35 miles north of Sheffield
  • 3-star hotel
  • 2 floors in property
More Photos Photo of Wheatleigh
From£300
Very good 4.0 /5 Guest 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 ~16.59 miles north of Sheffield
  • Mid-scale hotel
  • Gym is available on property
More Photos Photo of Canyon Ranch Lenox
From£67
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 ~16.89 miles north of Sheffield
  • 4-star Mountain hotel
  • Check in time: 4:00 PM
More Photos Image of Apple Tree Inn
From£75
Average 3.0 /5 Latest 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 ~17.04 miles north of Sheffield
  • High-end Rural hotel
  • Free comp. breakfast
More Photos Image of Brook Farm Inn
From£90
Very good 4.0 /5 Guest 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 ~17.24 miles north of Sheffield
  • Affordable Mountain property
  • Hotel has 3 meeting rooms
More Photos Image of Kemble Inn
From£198
Very good 4.0 /5 Recent Reviews Call BookMore Details
The Constance by The Lenox Collection 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 ~17.29 miles north of Sheffield
  • Four-star property
  • Free breakfast available
More Photos Exterior of The Constance by The Lenox Collection
From£168
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 ~17.36 miles north of Sheffield
  • 3-star hotel
  • Check-in: 14:00
More Photos hotel room
From£150
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 ~17.80 miles north of Sheffield
  • High-end property
  • Complimentary breakfast is offered
More Photos hotel room
From£56
Average 3.0 /5 Guest Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires
+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 ~18.03 miles north of Sheffield
  • 3-star Mountain hotel
  • Free complimentary breakfast
More Photos Photo of The Cornell Inn, Lenox & The Berkshires
From£45
Very good 4.0 /5 Review Score 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 ~18.59 miles north of Sheffield
  • High-end Mountain property
  • Hotel has 10 meeting rooms
More Photos Exterior of Eastover Estate & Retreat
From£81
Average 3.5 /5 Recent Reviews 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 ~19.15 miles north of Sheffield
  • Midscale Mountain hotel
  • 2 floors in hotel
More Photos Photo of Element Lenox Berkshires
From£37
Average 3.0 /5 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 ~19.47 miles north of Sheffield
  • Two-star Suburban hotel
More Photos Exterior of Life House Berkshires
From£36
Average 3.0 /5 Guest Reviews Call BookMore Details
Howard Johnson by Wyndham Lenox in Lenox
+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 ~19.67 miles north of Sheffield
  • Two-star Resort hotel
  • 2 floors in hotel
More Photos Exterior of Howard Johnson by Wyndham Lenox
From£48
Average 3.0 /5 Guest Reviews 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 ~20.19 miles north of Sheffield
  • 4-star Resort hotel
  • Check-in: 3PM
More Photos Exterior of Miraval Berkshires Resort & Spa - All Inclusive Adults Only
From£103
Average 3.0 /5 Guest Reviews Call BookMore Details
The Amselhaus
+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 ~20.21 miles south of Sheffield
  • Four star Riverfront hotel
  • 2 floors in hotel
More Photos hotel room
From£187
Very good 4.0 /5 Recent Reviews Call BookMore Details
Tiara Equest (The Inn at Richmond & Berkshire Equestrian Center : 802 State Rd.
+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 ~20.45 miles north of Sheffield
  • 3 star Rural property
  • 4 suites in hotel
More Photos hotel room
From£112
Very good 4.5 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-Lenox
+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 ~20.64 miles north of Sheffield
  • Mid-scale Mountain hotel
  • Fitness / Gym is on-site
More Photos Photo of Hampton Inn & Suites Berkshires-Lenox
From£81
Average 3.0 /5 Latest 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 ~20.69 miles north of Sheffield
  • 2-star property
  • Gym is available on property
More Photos Photo of The Yankee Trademark Collection by Wyndham
From£108
Very good 4.0 /5 Recent Reviews Call BookMore Details
Knights Inn 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 ~20.72 miles north of Sheffield
  • Two star Downtown hotel
  • Hotel has 16 rooms
More Photos Exterior of Knights Inn Lenox
From£27
Poor 2.0 /5 Latest Reviews Call BookMore Details
Lenox Inn : 525 Pittsfield Rd.
+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 ~20.96 miles north of Sheffield
  • Economical property
More Photos Photo of Lenox Inn
From£45
Poor 2.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1032 South St., Pittsfield, MA 01201 ~21.02 miles north of Sheffield
  • 3-star Suburban property
  • 4 floors in hotel
More Photos Photo of Hilton Garden Inn Lenox Pittsfield
From£71
Very good 4.0 /5 Guest Reviews Call BookMore Details
Berkshire Mountain Lodge : 8 Dan Fox Dr.
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
8 Dan Fox Dr., Pittsfield, MA 01201 ~21.37 miles north of Sheffield
  • Low Cost Mountain hotel
  • 146 suites in hotel
More Photos Photo of Berkshire Mountain Lodge
From£93
Very good 4.5 /5 Read Reviews Call BookMore Details
Best Western Plus Berkshire Hills Inn & Suites - Pittsfield
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
1350 West Housatonic St., Pittsfield, MA 01201 ~22.43 miles north of Sheffield
  • Three Star Rural property
  • 3 floors in property
More Photos Image of Best Western Plus Berkshire Hills Inn & Suites
From£63
Very good 4.5 /5 Guest Reviews Call BookMore Details
Americas Best Value Inn Torrington CT
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
395 Winsted Rd., Torrington, CT 06790 ~23.28 miles southeast of Sheffield
  • Cheap Suburban property
  • Fitness + Health Center
More Photos Image of Americas Best Value Inn Torrington CT
From£42
Poor 2.0 /5 Guest Reviews Call BookMore Details
Berkshire Inn in Pittsfield
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
150 West Housatonic St., Pittsfield, MA 01201 ~23.49 miles north of Sheffield
  • Cheap Downtown property
  • 36 sleeping rooms in hotel
More Photos Photo of Berkshire Inn
From£67
Average 3.0 /5 Review Score Call BookMore Details
St. Charles Hotel - Hudson
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
16 Park Place, Hudson, NY 12534 ~23.77 miles west of Sheffield
  • Low Cost Downtown property
  • Hotel has 34 rooms
More Photos Image of St. Charles Hotel
From£60
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn & Suites Pittsfield-Berkshires by IHG
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
1 West St., Pittsfield, MA 01201 ~23.86 miles north of Sheffield
  • 3-star Downtown hotel
  • 170 rooms in property
More Photos Photo of Holiday Inn & Suites Pittsfield-Berkshires by IHG
From£60
Average 3.0 /5 Latest Reviews Call BookMore Details
Hudson Whaler : 542 Warren St.
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
542 Warren St., Hudson, NY 12534 ~23.92 miles west of Sheffield
  • Affordable Downtown property
  • Fitness + Health Center
More Photos hotel room
From£56
Very good 4.0 /5 Latest Reviews Call BookMore Details
Hotel on North
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
297 North St., Pittsfield, MA 01201 ~24.18 miles north of Sheffield
  • High-end Downtown property
  • 6 suites in hotel
More Photos Photo of Hotel on North
From£112
Excellent 5.0 /5 Read Reviews Call BookMore Details

Next: See My Sheffield Hotels with Pricing

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?

The Windflower Inn, Hotel on North and Chambery Inn 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 Apple Tree Inn are the top 3 luxury hotels near Sheffield city center.

What hotels are closest to the city center of Sheffield?

The Windflower Inn, Quality Inn, and Fairfield Inn & Suites by Marriott Great Barrington Lenox are the properties closest to Sheffield city center.

What are the best independent hotels in Sheffield?

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

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

Quality Inn, Quality Inn and Black Swan Inn Lee Lenox An Ascend Hotel are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the best IHG hotels in Sheffield?

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

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