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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 30 B&B in Sheffield with updated reviews, rates, and availability.

The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Quiet, friendly, convenient"
The price is AED 530
AED 735 total
includes taxes & fees
12 May - 13 May
The Cornell Inn, Lenox & The Berkshires
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (258)
"Wonderful Location"
The price is AED 845
AED 991 total
includes taxes & fees
23 May - 24 May
Lakehouse Inn
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (100)
"We spent one night and loved the place. It's a beautiful, stately old inn. Our room was nicely appointed and very comfortable. Lucas made us feel at home, and cooked a marvelous breakfast. We'd highly recommend."
The price is AED 611
AED 702 total
includes taxes & fees
12 May - 13 May
Blackberry River Inn
Wilder House Berkshires
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (21)
"I’m a returning guest. The house is always charming, welcoming, comfortable and clean! The owner is very accommodating. "
The price is AED 562
AED 628 total
includes taxes & fees
21 May - 22 May
Wilder House Berkshires
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (378)
"Property is very clean, Bed was very comfortable, Owner is very attentive to stay and Breakfast is Amazing. Fresh eggs from her own hens. Will definitely return."
The price is AED 386
AED 444 total
includes taxes & fees
12 May - 13 May
Locust Tree Bed and Breakfast LLC
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (410)
"Nice"
The price is AED 735
AED 806 total
includes taxes & fees
9 Jun - 10 Jun
Shaker Mill Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is AED 698
AED 779 total
includes taxes & fees
12 May - 13 May
Chambery Inn
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"Beautiful place. Everything was perfect and so pretty. Great location, too. Will definitely return. "
The price is AED 1,441
AED 1,610 total
includes taxes & fees
14 May - 15 May
33 Main
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (282)
"Attentive staff. Pleasant accommodation located walkably close to wedding venue "
The price is AED 937
AED 1,060 total
includes taxes & fees
12 May - 13 May
Inn at Pine Plains
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"Very homy kind of Inn. Owner was very accommodative and friendly. Very safe place with great ambience. "
The price is AED 639
AED 714 total
includes taxes & fees
12 May - 13 May
Brook Farm Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (125)
"Very enjoyable comfortable stay"
The price is AED 988
AED 1,104 total
includes taxes & fees
12 May - 13 May
Devonfield Inn B&B
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"Great historic inn loaded with interesting common areas and furnishings."
The price is AED 622
AED 764 total
includes taxes & fees
26 May - 27 May
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is AED 2,530
AED 3,061 total
includes taxes & fees
15 May - 16 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Jenny's Country Manor
Interior

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (126)
"A beautiful country inn. Very comfortable and just like home "
The price is AED 514
AED 582 total
includes taxes & fees
12 May - 13 May
Jenny's Country Manor
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (85)
"The Inn was welcoming and comfortable with homemade cookies waiting for us at check in! The decor was especially inviting, we loved it! The staff that took our breakfast order, was equally warm, inviting, and accommodating. "
The price is AED 584
AED 631 total
includes taxes & fees
12 May - 13 May
Inn at Silver Maple Farm
Manor House Inn
Interior detail

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (135)
"Excellent bed and breakfast, room was clean and comfortable."
The price is AED 1,142
AED 1,267 total
includes taxes & fees
25 May - 26 May
Manor House Inn
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Beautiful rooms, wonderful hosts, been here several times and plan to come again. "
The price is AED 823
AED 919 total
includes taxes & fees
13 May - 14 May
Granville House
Tanglewood Suites
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
The price is AED 988
AED 988 total
includes taxes & fees
12 May - 13 May
Tanglewood Suites
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
The price is AED 1,561
AED 1,712 total
includes taxes & fees
12 May - 13 May
Inn at Kenmore Hall
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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Other property types in Sheffield

The Race Mountain House
Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (86)
"Place is great. Has a old farmhouse feel with an update. Lots of spots within the house for people to hang out. We did a family birthday get together and had a great time. "
Antique Farmhouse Totally Restored
Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (6)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is AED 1,855
AED 3,188 total
includes taxes & fees
12 May - 13 May
Guesthouse Cabin vacation rentals in Berkshire County
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.

Frequently asked questions

Searching for B&Bs in Sheffield?
If you’re looking for something a little more offbeat than the traditional hotel experience, a stay at a bed and breakfast might be the perfect option for your getaway. If your ideal vacation to Sheffield includes spending lots of time outside, Mount Everett State Reservation and Thom Reed UFO Monument Park are good spots to enjoy the scenery.
How do you know if a B&B is a good option for you?
Every B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook, the little details are what make bed and breakfasts a fun place to get away.
What are the top B&Bs in Sheffield?
Below are some B&Bs in the area: Wilder House Berkshires: 5 rooms. 0.3 mi (0.5 km) from the heart of Sheffield. Enjoy the free cooked breakfast and unique décor. The Cornell Inn, Lenox & The Berkshires: 18.1 mi (29.1 km) from the downtown core. Enjoy the free full breakfast and unique décor. Locust Tree Bed and Breakfast LLC: 7 rooms. Situated 6.8 mi (11 km) from the heart of Sheffield. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the heart of downtown. Enjoy the free cooked breakfast and outdoor pool. Lakehouse Inn: 14 rooms. Located 15.7 mi (25.2 km) from the core of Sheffield. Enjoy the free full breakfast and deli.
When should I book my B&B in Sheffield?
When you’re dreaming of a escape to Sheffield, year-round temperatures and rainfall may be important factors to consider. 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 is there to do in Sheffield?
When you want to spend some time in the great outdoors, Housatonic River and Mount Everett State Reservation are some notable spots. You might put Magnolia Bluffs Casino and Three Mile Pond Wildlife Management Area on your list if you want to see more of the area.
How can I get to and around Sheffield?
Planning your excursions in and around Sheffield is easier with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.