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Check prices for these dates

Next weekend
26 Sept - 28 Sept
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

Featured B&B in Sheffield and around

Our top choices for Sheffield bed & breakfast

Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (404)
"Peaceful area and great staff; Thank you for the service and experience "
The price is €103
includes taxes & fees
21 Sept - 22 Sept
Locust Tree Bed and Breakfast LLC
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (135)
"Vintage antique home. Close to road, but was quiet at night."
The price is €161
includes taxes & fees
17 Sept - 18 Sept
Blackberry River Inn
Wilder House Berkshires
Wilder House Berkshires Room 3

Wilder House Berkshires

2.0 star property
9.8 out of 10, Exceptional, (32)
"Beautiful and very comfortable house. Our hosts were always friendly and accessible, breakfast was delicious!"
The price is €192
includes taxes & fees
17 Sept - 18 Sept
Wilder House Berkshires
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is €144
includes taxes & fees
22 Sept - 23 Sept
The Cornell Inn, Lenox & The Berkshires
Manor House Inn
Interior detail

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (137)
"Excellent bed and breakfast, room was clean and comfortable."
The price is €279
includes taxes & fees
18 Sept - 19 Sept
Manor House Inn
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (280)
"A great getaway! Everything was excellent!"
The price is €162
includes taxes & fees
18 Sept - 19 Sept
Lakehouse Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
Chambery Inn
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (425)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is €169
includes taxes & fees
22 Sept - 23 Sept
Shaker Mill Inn
Granville House
Individually decorated, individually furnished, desk, laptop workspace

Granville House

3.0 star property
10.0 out of 10, Exceptional, (85)
"Beautiful place! Terri and Terry are the best!"
The price is €236
includes taxes & fees
18 Sept - 19 Sept
Granville House
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft)

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (160)
"Inn was gorgeous and staff exceptional!"
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, (129)
"The inn has an excellent location and amenities."
Devonfield Inn B&B
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 price is €382
includes taxes & fees
21 Sept - 22 Sept
The Inn at Stockbridge
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (492)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
The price is €138
includes taxes & fees
17 Sept - 18 Sept
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

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 €318
includes taxes & fees
30 Sept - 1 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
33 Main
Luxury Room, 1 King Bed, Bathtub

33 Main

4.0 star property
10.0 out of 10, Exceptional, (71)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is €588
includes taxes & fees
8 Oct - 9 Oct
33 Main
Tanglewood Suites
2 Bedrooms 1 Bath

Tanglewood Suites

2.5 star property
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
The price is €229
includes taxes & fees
17 Sept - 18 Sept
Tanglewood Suites
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is €318
includes taxes & fees
17 Sept - 18 Sept
Historic Susan B. Anthony Room - Cozy & Charming Stay
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (94)
"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "
The price is €190
includes taxes & fees
17 Sept - 18 Sept
Inn at Silver Maple Farm
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (293)
"Beautiful place. Accomadating staff. A lovely place to stay"
Inn at Pine Plains
Jenny's Country Manor
Exterior

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (130)
"Cool place in the Catskills! Under some renovations but well worth the stop. Big rooms. Comfy beds. Close to so much!"
The price is €135
includes taxes & fees
17 Sept - 18 Sept
Jenny's Country Manor
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

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent
" To whom it may concern, My wife & I were blessed beyond measures with Chris the recepcionista who was an amazing incredible human being who treated us like family. We needed some direction to southbridge Ma. He explain to us the best way to get there and back to the hotel. Also the other gentleman working along side of him also assisted us as well. Thank you for this beautiful experience and to let you know that we will come again. Please give our love to the precious lady housekeeper who blessed us as well. "
Angel 1-night trip
Posted 14 hours ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Find out more about Sheffield

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,685
Accommodation
29 B&B
Lowest Price
€103
Highest Price
€588

Frequently asked questions

Searching for B&Bs in Sheffield?
If you're looking for something a little quirkier than your standard hotel, a stay at a bed and breakfast could be the perfect alternative for your holiday. If your ideal holiday to Sheffield includes spending lots of time outside, Thom Reed UFO Monument Park and Bartholomews Cobble are good spots to enjoy the scenery.
How do you know if a B&B is the best choice for you?
B&Bs all have a unique charm — whether it's a cosy reading space or a beautiful dining room, the little details are what make bed and breakfasts the perfect escape.
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 decor. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the city centre. Enjoy the free cooked breakfast and outdoor pool. The Cornell Inn, Lenox & The Berkshires: Situated 18.1 mi (29.1 km) from the heart of Sheffield. Enjoy the free full breakfast and unique decor. Locust Tree Bed and Breakfast LLC: 7 rooms. 6.8 mi (11 km) from the city centre.
What's the best time of year to 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 temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Sheffield?
When you want to spend some time in the great outdoors, Housatonic River and Thom Reed UFO Monument Park are some notable spots. You should put Magnolia Bluffs Casino and Mount Everett State Reservation on your list if you want to see more of the area.
How can I get to and around Sheffield?
Mapping out your trip in and around Sheffield is easy 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. Otherwise, look 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 a rental car for your journey.

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