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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 : 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 ~4.60 miles northwest of Sheffield
  • 3-star Mountain hotel
  • 2 meeting rooms in property
More Photos Photo of The Windflower Inn
From$185
Excellent 5.0 /5 Recent Reviews Call BookMore Details
Tired of clicking around? Talk to an expert Hotel Planner: (855) 276-7561 or say...
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Quality Inn - 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 ~5.62 miles north of Sheffield
  • Low priced Rural property
  • Check in time: 3:00pm
More Photos Image of Quality Inn
From$100
Very good 4.0 /5 Read Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi 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
249 Stockbridge Rd., Great Barrington, MA 01230 Website ~6.70 miles north of Sheffield
  • 3 star Resort property
  • Fitness + Health Center
More Photos Photo of Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshi
From$109
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Travelodge by Wyndham Great Barrington Berkshires : 400 Stockbridge Rd.
+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 ~7.04 miles north of Sheffield
  • Cheap Resort property
  • Free breakfast
More Photos Image of Travelodge by Wyndham Great Barrington Berkshires
From$47
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 ~7.14 miles north of Sheffield
  • Midscale Mountain hotel
  • Check-in time: 3:00pm
More Photos Image of Holiday Inn Express Great Barrington
From$89
Very good 4.0 /5 Read Reviews Call BookMore Details
Blackberry River Inn
+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 ~9.32 miles southeast of Sheffield
  • 3 star property
  • Check-in: 15:00
More Photos Image of Blackberry River Inn
From$109
Very good 4.0 /5 Review Score 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 ~11.32 miles southwest of Sheffield
  • Midscale Rural property
  • 38 rooms in property
More Photos Exterior of Wake Robin Inn
From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Manor House Inn
+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 ~11.57 miles southeast of Sheffield
  • Affordable Rural property
  • 9 sleeping rooms in hotel
More Photos Image of Manor House Inn
From$240
Very good 4.0 /5 Latest 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 ~12.02 miles north of Sheffield
  • Midscale Rural hotel
  • Hotel has 35 suites
More Photos Image of The Red Lion Inn
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort : 190 Meadow St.
+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 ~12.06 miles north of Sheffield
  • Affordable Mountain hotel
  • Hotel has 3 floors
More Photos Exterior of Holiday Inn Club Vacations Oak N Spruce Resort
From$89
Very good 4.0 /5 Review Score Call BookMore Details
Interlaken Inn & Resort - 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 ~12.19 miles southwest of Sheffield
  • Midscale Resort property
  • Hotel has 2 floors
More Photos Exterior of Interlaken Inn & Resort
From$209
Very good 4.0 /5 Recent Reviews Call BookMore Details
Econo Lodge Lee - Great Barrington : 980 Pleasant St.
+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 ~12.58 miles northeast of Sheffield
  • Two-star property
  • Free comp. breakfast
More Photos Exterior of Econo Lodge Lee - Great Barrington
From$48
Average 3.0 /5 Guest Reviews Call BookMore Details
Applegate Inn
+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 ~14.31 miles northeast of Sheffield
  • Mid-scale Rural hotel
  • 6 suites in hotel
More Photos Image of Applegate Inn
From$160
Very good 4.0 /5 Guest Reviews Call BookMore Details
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Pilgrim Inn - 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 ~14.37 miles northeast of Sheffield
  • Affordable property
  • Check in time: 3:00 PM
More Photos Image of Pilgrim Inn
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
33 Main
+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 ~14.49 miles northeast of Sheffield
  • Luxury 5-star hotel
More Photos hotel room
From$200
Average 3.0 /5 Reviews Call BookMore Details
Need some questions answered? Talk to an expert Hotel Planner: (855) 276-7561 or say...
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Chambery Inn in 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 ~14.69 miles north of Sheffield
  • 3 star property
  • Check-in time: 14:00
More Photos Exterior of Chambery Inn
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 ~14.83 miles north of Sheffield
  • Economical property
  • 16 sleeping rooms in hotel
More Photos Photo of Pleasant Valley Motel West Stockbridge
From$60
Average 3.0 /5 Read 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 ~15.07 miles north of Sheffield
  • Inexpensive property
  • 23 sleeping rooms in hotel
More Photos Photo of Rodeway Inn
From$60
Average 3.0 /5 Latest 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 ~15.35 miles north of Sheffield
  • 3-star Lake hotel
  • Check-in time: 3:00 PM
More Photos Photo of Quality Inn
From$65
Very good 4.0 /5 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 ~15.36 miles north of Sheffield
  • 3-star Lake hotel
  • Hotel has 2 floors
More Photos Photo of Black Swan Inn Lee Lenox An Ascend Hotel
From$60
Very good 4.0 /5 Latest Reviews Call BookMore Details
Seven Hills Inn : 40 Plunkett St.
+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 property
  • Has environment-friendly policy See more
More Photos Image of Seven Hills Inn
From$184
Very good 4.5 /5 Review Score 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 ~16.37 miles north of Sheffield
  • Mid-scale hotel
  • 2 floors in property
More Photos Exterior of Wheatleigh
From$400
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Canyon Ranch Lenox in 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 ~16.61 miles north of Sheffield
  • Mid-scale property
  • Fitness center on property
More Photos Exterior of Canyon Ranch Lenox
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 ~16.91 miles north of Sheffield
  • High-end Mountain property
  • Hotel has 34 rooms
More Photos Exterior of Apple Tree Inn
From$100
Average 3.0 /5 Hotel 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 ~17.06 miles north of Sheffield
  • Four-star Rural property
  • Hotel has 15 rooms
More Photos Exterior of Brook Farm Inn
From$120
Very good 4.0 /5 Review Score Call BookMore Details
Kemble Inn in 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 ~17.26 miles north of Sheffield
  • 3 star Mountain property
  • 12 suites in property
More Photos Exterior of Kemble Inn
From$265
Very good 4.0 /5 Read Reviews Call BookMore Details
The Constance by The Lenox Collection - 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 ~17.31 miles north of Sheffield
  • Expensive hotel
  • 3 floors in hotel
More Photos Photo of The Constance by The Lenox Collection
From$225
Average 3.0 /5 Recent 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 ~17.38 miles north of Sheffield
  • 3 star property
  • Check in: 14:00
More Photos hotel room
From$200
Average 3.0 /5 Guest 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 ~17.83 miles north of Sheffield
  • 4-star property
  • Hotel has 2 floors
More Photos hotel room
From$75
Average 3.0 /5 Latest Reviews Call BookMore Details
The Cornell Inn, Lenox & The Berkshires in 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 ~18.06 miles north of Sheffield
  • Midscale Mountain hotel
  • Complimentary breakfast is offered
More Photos Image of The Cornell Inn, Lenox & The Berkshires
From$60
Very good 4.0 /5 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 ~18.62 miles north of Sheffield
  • Expensive Mountain hotel
  • Hotel has 10 meeting rooms
More Photos Exterior of Eastover Estate & Retreat
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 ~19.49 miles north of Sheffield
  • Two-star Suburban property
  • Check in: 2pm
More Photos Exterior of Life House Berkshires
From$49
Average 3.0 /5 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 ~19.70 miles north of Sheffield
  • Cheap Resort hotel
  • 2 floors in property
More Photos Image of Howard Johnson by Wyndham Lenox
From$65
Average 3.0 /5 Guest 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 ~20.22 miles north of Sheffield
  • Four-star Resort hotel
  • 10 conference rooms in property
More Photos Photo of Miraval Berkshires Resort & Spa - All Inclusive Adults Only
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 ~20.24 miles south of Sheffield
  • High end Riverfront property
  • 2 floors in hotel
More Photos hotel room
From$250
Very good 4.0 /5 Latest 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 ~20.48 miles north of Sheffield
  • Affordable Rural hotel
  • Check-in time: 3:00 p.m.
More Photos hotel room
From$150
Very good 4.5 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Berkshires-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 ~20.67 miles north of Sheffield
  • 3-star Mountain property
  • Check in time: 3:00 pm
More Photos Photo of Hampton Inn & Suites Berkshires-Lenox
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 ~20.72 miles north of Sheffield
  • Low-priced hotel
  • Fitness + Health Center
More Photos Photo of Yankee Inn
From$145
Very good 4.0 /5 Recent Reviews Call BookMore Details
Knights Inn Lenox in 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 ~20.75 miles north of Sheffield
  • Low Cost Downtown hotel
  • Check in: 2.00 pm
More Photos Exterior of Knights Inn Lenox
From$37
Poor 2.0 /5 Guest Reviews Call BookMore Details
Lenox Inn
+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 ~20.99 miles north of Sheffield
  • Inexpensive hotel
  • 18 rooms in hotel
More Photos Exterior of Lenox Inn
From$60
Poor 2.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Lenox Pittsfield in 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 ~21.05 miles north of Sheffield
  • Mid-scale Suburban property
  • 3 suites in property
More Photos Photo of Hilton Garden Inn Lenox Pittsfield
From$95
Very good 4.0 /5 Read Reviews Call BookMore Details
Berkshire Mountain Lodge
+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 ~21.40 miles north of Sheffield
  • Cheap Mountain property
  • 2 meeting rooms in hotel
More Photos Exterior of Berkshire Mountain Lodge
From$125
Very good 4.5 /5 Recent Reviews 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 ~22.47 miles north of Sheffield
  • 3-star Rural hotel
  • 3 floors in property
More Photos Exterior of Best Western Plus Berkshire Hills Inn & Suites
From$79
Very good 4.0 /5 Latest Reviews Call BookMore Details
Americas Best Value Inn Torrington CT
+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 ~23.33 miles southeast of Sheffield
  • Cheap Suburban hotel
  • Fitness / Gym is on-site
More Photos Image of Americas Best Value Inn Torrington CT
From$57
Poor 2.0 /5 Guest Reviews Call BookMore Details
Berkshire Inn - Pittsfield
+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 ~23.52 miles north of Sheffield
  • Inexpensive Downtown property
  • Check in time: 1500
More Photos Photo of Berkshire Inn
From$90
Average 3.0 /5 Reviews Call BookMore Details
St. Charles Hotel
+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 ~23.78 miles west of Sheffield
  • Cheap Downtown hotel
  • Complimentary breakfast is offered
More Photos Photo of St. Charles Hotel
From$80
Average 3.0 /5 Hotel 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 ~23.89 miles north of Sheffield
  • 3 star Downtown property
  • 170 rooms in hotel
More Photos Image of Holiday Inn & Suites Pittsfield-Berkshires by IHG
From$80
Average 3.0 /5 Review Score 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 ~23.93 miles west of Sheffield
  • Mid-scale Downtown hotel
  • Hotel has 3 floors
More Photos hotel room
From$75
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hotel on North : 297 North St.
+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 ~24.21 miles north of Sheffield
  • Four-star Downtown property
  • Hotel has an eco-friendly policy Learn more
More Photos Image of Hotel on North
From$150
Excellent 5.0 /5 Hotel Reviews Call BookMore Details
The Nest Hudson Hotel : 330 Union St.
+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 ~24.29 miles west of Sheffield
  • Four-star Downtown property
  • Check in: 3:00
More Photos Photo of The Nest Hudson Hotel
From$200
Very good 4.5 /5 Recent 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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