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Check prices for these dates

Next weekend
19 Sept - 21 Sept
In two weeks
26 Sept - 28 Sept
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov

Featured B&B in Sheffield

Our top choices for Sheffield bed & breakfast

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, (1001)
"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 RM537
RM764 total
includes taxes & fees
16 Sept - 17 Sept
The Cornell Inn, Lenox & The Berkshires
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (134)
"Vintage antique home. Close to road, but was quiet at night."
The price is RM691
RM794 total
includes taxes & fees
15 Sept - 16 Sept
Blackberry River Inn
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (402)
"Peaceful area and great staff; Thank you for the service and experience "
The price is RM441
RM507 total
includes taxes & fees
14 Sept - 15 Sept
Locust Tree Bed and Breakfast LLC
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (490)
"Nice quaint out of the ordinary vacation experience. "
The price is RM677
RM757 total
includes taxes & fees
14 Sept - 15 Sept
Whistler's Inn Bed & Breakfast
Wilder House Berkshires
1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (29)
"Beautiful and very comfortable house. Our hosts were always friendly and accessible, breakfast was delicious!"
The price is RM849
RM948 total
includes taxes & fees
15 Sept - 16 Sept
Wilder House Berkshires
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 RM677
RM742 total
includes taxes & fees
14 Sept - 15 Sept
Shaker Mill Inn
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 RM878
RM984 total
includes taxes & fees
24 Sept - 25 Sept
Inn at Silver Maple Farm
Tanglewood Suites
1 bedroom, premium bedding, iron/ironing board, free WiFi

Tanglewood Suites

2.5 star property
6.6 out of 10, (21)
"This is a VRBO !!! Not a Bed & Breakfast. Not on Main Street in Stockbridge! Not called the Tanglewood Suites. Total misrepresentation. Cash only payments!!?!! Lousy old croissants and homemade yogurt with no sealed package or date. Homeowner called repeatedly demanding an arrival time!!! Stay elsewhere!"
The price is RM1,131
RM1,131 total
includes taxes & fees
14 Sept - 15 Sept
Tanglewood Suites
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
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
Changing Times Boutique Country Lodging
Porch

Changing Times Boutique Country Lodging

3.5 star property
10.0 out of 10, Exceptional, (106)
"Great experience, looking forward to staying again."
The price is RM735
RM824 total
includes taxes & fees
17 Sept - 18 Sept
Changing Times Boutique Country Lodging
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (279)
"The Inn is lovely. Friendly, welcoming and upbeat staff and went out of their way to make sure we were happy. The room was very comfortable. The lake is sweet and beautiful. Breakfast was DELISH! Great stay! I highly recommend! "
The price is RM643
RM754 total
includes taxes & fees
15 Sept - 16 Sept
Lakehouse Inn
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 RM588
RM666 total
includes taxes & fees
14 Sept - 15 Sept
Jenny's Country Manor
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 RM1,047
RM1,169 total
includes taxes & fees
15 Sept - 16 Sept
Granville House
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 RM1,301
RM1,573 total
includes taxes & fees
29 Sept - 30 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Brook Farm Inn
1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (160)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
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 RM1,244
RM1,381 total
includes taxes & fees
14 Sept - 15 Sept
Manor House Inn
33 Main
Premium bedding, individually decorated, iron/ironing board, free WiFi

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 RM2,601
RM2,905 total
includes taxes & fees
8 Oct - 9 Oct
33 Main
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"This is a beautiful property straight out of a magazine. Service was impeccable"
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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Top Sheffield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Michelle and Maddie made my stay very pleasant. When I first came in Maddie helped me get settled.Needed an adjustment to my room and she took care of it. Michelle made sure that everything was available for breakfast for me in spite of the pancake maker having a temporary clog. So nice to stay at a place where people will make the extra effort! Both women helped me with my bags. Great place to stay."
Iris 1-night trip
Posted 3 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Sheffield

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,680
Accommodation
29 B&B
Lowest Price
RM441
Highest Price
RM2,601

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.