Find Boutique Hotels in Sheffield, MA

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Check availability on Sheffield Boutique Hotels

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Recommended hotels in Sheffield

Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
The price is NT$5,054
NT$5,645 total
includes taxes & fees
Dec 14 - Dec 15
Wilder House Berkshires
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is NT$4,087
NT$4,565 total
includes taxes & fees
Dec 18 - Dec 19
Element Lenox Berkshires
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay there!! Very friendly staff"
United States
Ann
The price is NT$2,333
NT$2,606 total
includes taxes & fees
Dec 24 - Dec 25
The Yankee, Trademark Collection by Wyndham
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is NT$3,400
NT$3,730 total
includes taxes & fees
Dec 14 - Dec 15
Shaker Mill Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is NT$2,464
NT$2,753 total
includes taxes & fees
Dec 14 - Dec 15
Howard Johnson by Wyndham Lenox
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (707)
"Great hospitality "
United States
regina maria
The price is NT$3,338
NT$3,729 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1002)
"Clean room, nice location "
United States
Devron
The price is NT$2,360
NT$2,636 total
includes taxes & fees
Dec 28 - Dec 29
Quality Inn Great Barrington
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (804)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sheffield Hotel Reviews

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Frequently asked questions

What's there to see and do in Sheffield?
Once you've decided where you'd like to stay in historic Sheffield, consider what to do for fun during your trip. Activities and attractions to experience around Sheffield include Housatonic River, Magnolia Bluffs Casino, and Ashley House. You might also like to explore more of the area and take in additional sights like Three Mile Pond Wildlife Management Area, Mount Everett State Reservation, and Mahaiwe Performing Arts Center while you're here.
What kind of weather should I plan for when I travel to Sheffield?
Getting an idea of what to expect from the weather in Sheffield will help you enjoy your stay to the fullest. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to my boutique hotel in Sheffield?
You have a few options for getting to Sheffield. The nearest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the heart of the city. If you'd like to venture out around the area, consider renting a car to take in more sights.