A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Book Sheffield Bed & Breakfast

Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Sheffield bed & breakfast

1. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (67 reviews)
"Perfect little b&b."
United States
Mark
$197 nightly
The price is $220
Sep 27 - Sep 28
Total with taxes and fees
Wilder House Berkshires
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

2. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (448 reviews)
"The whole vibe of the B&B was so simple and perfect. 10/10 will stay again."
United States
Nicholas
$105 nightly
The price is $121
Sep 27 - Sep 28
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

3. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (222 reviews)
"Great breakfast"
United States
Brian
$140 nightly
The price is $161
Sep 30 - Oct 1
Total with taxes and fees
Blackberry River Inn
A patio with a round metal table, a glass of white wine, and a red umbrella.

4. Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (141 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
$288 nightly
The price is $320
Sep 29 - Sep 30
Total with taxes and fees
Manor House Inn
A dining table with pastries, a coffee pot, and a vase of sunflowers.

5. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (106 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
$224 nightly
The price is $250
Sep 27 - Sep 28
Total with taxes and fees
Granville House
A two-story building with a sign reading "Chambéry Inn".

6. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (388 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
$282 nightly
The price is $315
Oct 27 - Oct 28
Total with taxes and fees
Chambery Inn
A large, two-story house with a well-maintained lawn and a fence.

7. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
$409 nightly
The price is $457
Oct 25 - Oct 26
Total with taxes and fees
Devonfield Inn B&B

8. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
$460 nightly
The price is $514
Sep 27 - Sep 28
Total with taxes and fees
The Inn at Stockbridge
A garden with a white gazebo, a brick pathway, and various plants and flowers.

9. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (518 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
$158 nightly
The price is $177
Oct 5 - Oct 6
Total with taxes and fees
Whistler's Inn Bed & Breakfast
A two-story house with a brick entrance and a white facade.

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (118 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$537 nightly
The price is $600
Oct 12 - Oct 13
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

11. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (117 reviews)
"We had a very pleasant stay at this. Eautiful country property. Check in was smooth and instructions were easy to follow. Our room, in the main building was well appointed. The bed was super comfortable and the amenities were fine. Breakfast was great! Common areas were lovely and inviting, and the s’mores kits in the lobby were just the thing for an evening around the outdoor fire pit. Highly recommend for anyone seeking a serene country setting."
United States
Jody
$214 nightly
The price is $240
Sep 28 - Sep 29
Total with taxes and fees
Inn at Silver Maple Farm
A red building with a sign reading "Shaker Mill Inn."

12. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (475 reviews)
"Wonderful place to stay!"
United States
Mervin
$179 nightly
The price is $196
Oct 1 - Oct 2
Total with taxes and fees
Shaker Mill Inn
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

13. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$267 nightly
The price is $306
Oct 27 - Oct 28
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
A snow-covered outdoor area with a patio, seating, and a covered dining area.

14. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
$160 nightly
The price is $179
Oct 27 - Oct 28
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

15. Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (317 reviews)
"Great place! Comfy and charming!!"
United States
Mary
$248 nightly
The price is $280
Oct 11 - Oct 12
Total with taxes and fees
Inn at Pine Plains
A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

16. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (127 reviews)
"A great place to stay!"
United States
Thomas
$200 nightly
The price is $224
Sep 28 - Sep 29
Total with taxes and fees
Changing Times Boutique Country Lodging
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

17. Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$299 nightly
The price is $343
Sep 27 - Sep 28
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
A porch with a white railing, a potted plant, and a view of a garden.

18. Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
$375 nightly
The price is $430
Sep 28 - Sep 29
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

19. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$267 nightly
The price is $306
Oct 27 - Oct 28
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

20. Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
$409 nightly
The price is $469
Oct 20 - Oct 21
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"If you want a perfect New England experience, this is the place. The hotel is amazing, it’s older so don’t think you’re going to walk into a modern place, but don’t let that deter you, the vibe is great! Will definitely stay here again."
Michelle 2-night trip
Posted 1 hour ago
The Red Lion Inn

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,942
Accommodation
41 B&B
Lowest Price
$121
Highest Price
$600

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.

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