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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 & 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
  • 13 rooms in hotel
More PhotosExterior of The Windflower Inn
From$185
Excellent 5.0 /5Guest Reviews CallBookMore Details
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Days Inn by Wyndham 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 ~5.62 miles north of Sheffield
  • Inexpensive Rural hotel
  • Hotel has 2 floors
More PhotosImage of Days Inn by Wyndham Great Barrington
From$100
Very Good 4.0 /5Reviews CallBookMore Details
Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berks
+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 ~6.70 miles north of Sheffield
  • Mid-scale Resort property
  • Complimentary breakfast is offered
More PhotosExterior of Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berks
From$109
Very Good 4.0 /5Recent Reviews CallBookMore 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 ~7.04 miles north of Sheffield
  • Inexpensive Resort hotel
  • Complimentary breakfast is offered
More PhotosImage of Travelodge by Wyndham Great Barrington Berkshires
From$47
Average 3.5 /5Review Score CallBookMore Details
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
+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 ~7.09 miles north of Sheffield
  • Affordable Mountain hotel
  • Hotel has a green policy See policy
More PhotosExterior of Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
From$80
Average 3.0 /5Reviews CallBookMore 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
  • Midscale hotel
  • 17 sleeping rooms in hotel
More PhotosExterior of Blackberry River Inn
From$109
Very Good 4.0 /5Reviews CallBookMore Details
Wake Robin Inn : 106 Sharon Rd.
+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
  • Mid-scale Rural hotel
  • Hotel has an eco-friendly policy See more
More PhotosExterior of Wake Robin Inn
From$89
Average 3.0 /5Recent Reviews CallBookMore 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
  • 3 star Rural property
  • Free complimentary breakfast
More PhotosPhoto of Manor House Inn
From$240
Very Good 4.0 /5Review Score CallBookMore Details
The Red Lion Inn in 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 ~12.05 miles north of Sheffield
  • Affordable Rural property
  • 125 sleeping rooms in hotel
  • Fantastic service
  • Great desserts & fruits
More PhotosPhoto of The Red Lion Inn
From$229
Very Good 4.0 /5Guest Reviews CallBookMore Details
Holiday Inn Club Vacations Oak N Spruce Resort in 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 ~12.06 miles north of Sheffield
  • Three Star hotel
  • 334 suites in property
More PhotosImage of Holiday Inn Club Vacations Oak N Spruce Resort
From$80
Very Good 4.0 /5Latest Reviews CallBookMore Details
Interlaken Inn & Resort
+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
  • Three Star Resort property
  • Has environment-friendly policy See policy
  • Food is to die for
  • Nice building
More PhotosExterior of Interlaken Inn & Resort
From$209
Very Good 4.0 /5Recent Reviews CallBookMore 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 ~12.58 miles northeast of Sheffield
  • Two star property
  • Free comp. breakfast
More PhotosImage of Econo Lodge Lee - Great Barrington
From$48
Average 3.0 /5Latest Reviews CallBookMore Details
Applegate Inn - Lee
+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
  • 3-star Rural hotel
  • Check in: 2 pm
  • Popular among couples
  • Excellent hotel
More PhotosPhoto of Applegate Inn
From$160
Very Good 4.0 /5Reviews CallBookMore Details
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Quality 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
170 Housatonic St., Lee, MA 01238 ~14.35 miles northeast of Sheffield
  • Economical property
  • Check-in time: 11:00 AM
More PhotosExterior of Quality Inn
From$47
Average 3.0 /5Latest Reviews CallBookMore Details
Pilgrim Inn
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
165 Housatonic St., Lee, MA 01238 ~14.37 miles northeast of Sheffield
  • Mid-scale property
  • Check-in: 3:00 PM
More PhotosPhoto of Pilgrim Inn
From$80
Average 3.0 /5Recent Reviews CallBookMore Details
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33 Main - Lenox
+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 5 star property
More Photoshotel room
From$200
Average 3.0 /5Reviews CallBookMore Details
Chambery Inn : 199 Main St.
+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
  • Midscale hotel
  • Check-in time: 14:00
More PhotosExterior of Chambery Inn
From$90
Very Good 4.5 /5Latest Reviews 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
  • 2-star hotel
  • 16 rooms in property
More PhotosImage of Pleasant Valley Motel West Stockbridge
From$60
Average 3.0 /5Guest Reviews CallBookMore Details
Rodeway Inn - Lee
+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
  • 2 star property
  • Hotel has 23 rooms
More PhotosExterior of Rodeway Inn
From$60
Average 3.0 /5Read Reviews CallBookMore Details
Black Swan Inn Lee Lenox An Ascend Hotel in 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 Website ~15.36 miles north of Sheffield
  • Three Star Lake property
  • Comp. Breakfast
More PhotosImage of Black Swan Inn Lee Lenox An Ascend Hotel
From$60
Very Good 4.0 /5Review Score 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
  • High-end Resort hotel
  • Has environment-friendly policy See policy
More PhotosPhoto of Seven Hills Inn
From$184
Very Good 4.5 /5Hotel Reviews CallBookMore Details
Wheatleigh
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
11 Hawthorne Rd., Lenox, MA 01240 ~16.37 miles north of Sheffield
  • 3-star hotel
  • Check in time: 16:00
More PhotosImage of Wheatleigh
From$90
Average 3.0 /5Reviews CallBookMore 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 ~16.61 miles north of Sheffield
  • 3 star hotel
  • Fitness / Gym is on-site
More PhotosImage of Canyon Ranch Lenox
From$90
Average 3.0 /5Latest Reviews CallBookMore 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 hotel
  • Hotel has 34 rooms
More PhotosExterior of Apple Tree Inn
From$100
Average 3.0 /5Review Score CallBookMore Details
Brook Farm Inn : 15 Hawthorne St.
+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
  • Expensive Rural property
  • Check-in time: 3 pm
More PhotosExterior of Brook Farm Inn
From$120
Very Good 4.5 /5Guest Reviews CallBookMore Details
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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?

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, Days Inn by Wyndham Great Barrington, 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?

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

What are the most popular IHG hotels in Sheffield?

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

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