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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

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, (1000)
"Lovely, comfortable B&B with a nice feel. We plan to return."
The price is $200
includes taxes & fees
$179 per night
May 1 - May 2
The Cornell Inn, Lenox & The Berkshires
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (257)
"Wonderful Location"
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 $191
includes taxes & fees
$166 per night
May 5 - May 6
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 $171
includes taxes & fees
$153 per night
May 6 - May 7
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 $121
includes taxes & fees
$105 per night
May 1 - May 2
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"
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 $212
includes taxes & fees
$190 per night
May 11 - May 12
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 $438
includes taxes & fees
$392 per night
May 4 - May 5
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 $288
includes taxes & fees
$255 per night
May 4 - May 5
Inn at Pine Plains
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (151)
"Very homy kind of Inn. Owner was very accommodative and friendly. Very safe place with great ambience. "
The price is $194
includes taxes & fees
$174 per night
May 1 - May 2
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, (124)
"Very enjoyable comfortable stay"
The price is $300
includes taxes & fees
$269 per night
May 1 - May 2
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 $222
includes taxes & fees
$199 per night
May 1 - May 2
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 $833
includes taxes & fees
$746 per night
May 15 - May 16
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 $158
includes taxes & fees
$140 per night
May 1 - May 2
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)
"Everything about our stay in The Loft was wonderful! The hot breakfast each morning was incredible. The entire inn was very clean and well kept. We will definitely be back! "
The price is $161
includes taxes & fees
$149 per night
May 1 - May 2
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 $345
includes taxes & fees
$311 per night
May 22 - May 23
Manor House Inn
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"
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 $250
includes taxes & fees
$224 per night
May 1 - May 2
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 $269
includes taxes & fees
$269 per night
May 1 - May 2
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 $466
includes taxes & fees
$425 per night
May 1 - May 2
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

Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (36)
"The property was centrally located for skiing, and was a comfortable stay."
The price is $441
includes taxes & fees
$395 per night
May 13 - May 14
Cheerful 3-bedroom cottage with woodstove
Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is $865
includes taxes & fees
$774 per night
May 5 - May 6
Guesthouse Cabin vacation rentals in Berkshire County
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
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

What are the most popular Sheffield Bed and Breakfasts?
Wilder House Berkshires is an exceptional choice for travelers seeking a memorable stay in Sheffield, boasting an outstanding 10.0 rating. With complimentary cooked breakfasts that highlight local flavors, guests can start their day in the most delightful way. The attentive service ensures that every need is met, setting the stage for a truly relaxing getaway.
What is the nightly rate for a Bed and Breakfast in Sheffield?
Prices for B&Bs in Sheffield often vary, but you can find a great deal from $121 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Sheffield B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Sheffield?
The best time to book a B&B in Sheffield is during the late spring and early summer months, particularly from May to July. This period witnesses a delightful influx of visitors drawn to the vibrant city life, lush green parks, and a multitude of festivals and events that showcase Sheffield’s unique culture. The pleasant weather, typically ranging from the mid-50s to the low 70s Fahrenheit, creates an inclusive setting for outdoor activities and sightseeing.

May is particularly charming, as the city bursts into bloom, making it great for leisurely strolls through the beautiful Botanical Gardens or exploring the picturesque Peak District, which is just a short drive away. The longer days and mild temperatures provide an ideal setting for enjoying numerous outdoor cafes and dining experiences that Sheffield has to offer.

For those seeking a more budget-friendly option, consider visiting in December. This month, while cooler, invites visitors to enjoy the festive spirit of Christmas markets and seasonal events, providing a cozy charm that many travelers appreciate.
What is the difference between a Sheffield B&B and a hotel?
Every Sheffield B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Sheffield B&Bs.