A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Book Sheffield Bed & Breakfast

Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

Our top choices for Sheffield bed & breakfast

Interior detail

1. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (70 reviews)
"Perfect little b&b."
United States
Mark
$206 nightly
The price is $231
Nov 2 - Nov 3
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, (451 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
$105 nightly
The price is $121
Oct 18 - Oct 19
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, (235 reviews)
"Quiet room Wonderful breakfast Pleasant atmosphere"
United States
Donna
$190 nightly
The price is $219
Oct 19 - Oct 20
Total with taxes and fees
Blackberry River Inn
A dining table with pastries, a coffee pot, and a vase of sunflowers.

4. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (108 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
$254 nightly
The price is $284
Oct 25 - Oct 26
Total with taxes and fees
Granville House
A patio with a round metal table, a glass of white wine, and a red umbrella.

5. 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
$325 nightly
The price is $360
Oct 19 - Oct 20
Total with taxes and fees
Manor House Inn
A two-story house with a brick entrance and a white facade.

6. 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, (119 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$393 nightly
The price is $439
Nov 1 - Nov 2
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

7. 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
$383 nightly
The price is $428
Nov 1 - Nov 2
Total with taxes and fees
The Inn at Stockbridge
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

8. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveler
$270 nightly
The price is $302
Oct 26 - Oct 27
Total with taxes and fees
The Red Door B&B
A large, two-story house with a well-maintained lawn and a fence.

9. 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
$369 nightly
The price is $412
Nov 2 - Nov 3
Total with taxes and fees
Devonfield Inn B&B
A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

10. 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
Oct 19 - Oct 20
Total with taxes and fees
Changing Times Boutique Country Lodging
A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

11. Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (318 reviews)
"good location/ walkable to down town !"
United States
teresina
$228 nightly
The price is $258
Oct 29 - Oct 30
Total with taxes and fees
Inn at Pine Plains
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, (479 reviews)
"Very nice Inn in West Stockbridge. Easy walk to center of town and short drive to all the Berkshires attractions. Room was very quiet and the grounds are wonderful. Highly recommended!"
United States
Steven
$125 nightly
The price is $137
Nov 16 - Nov 17
Total with taxes and fees
Shaker Mill Inn
A two-story building with a sign reading "Chambéry Inn".

13. 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
$264 nightly
The price is $295
Oct 21 - Oct 22
Total with taxes and fees
Chambery Inn
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

14. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
$174 nightly
The price is $195
Nov 8 - Nov 9
Total with taxes and fees
Inn at Silver Maple Farm
A snow-covered outdoor area with a patio, seating, and a covered dining area.

15. 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)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
$160 nightly
The price is $179
Oct 27 - Oct 28
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
A garden with a white gazebo, a brick pathway, and various plants and flowers.

16. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (519 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
$188 nightly
The price is $210
Oct 19 - Oct 20
Total with taxes and fees
Whistler's Inn Bed & Breakfast
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

17. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$283 nightly
The price is $324
Oct 27 - Oct 28
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$283 nightly
The price is $324
Oct 27 - Oct 28
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A porch with a white railing, a potted plant, and a view of a garden.

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

Cozy Carriage House room with a double bed and private balcony
Lenox
$346 nightly
The price is $396
Nov 1 - Nov 2
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
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
$328 nightly
The price is $375
Nov 4 - Nov 5
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
"Good stay"
Jared 1-night trip
Posted less than an hour ago
The Red Lion Inn

Find out more about Sheffield

Sheffield B&B information

Number of reviews
2,660
Accommodation
41 B&B
Lowest Price
$121
Highest Price
$439

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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