20 Best B&B in Sheffield, MA - Bed and Breakfast from $120

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Our top choices for Sheffield bed & breakfast

1. Wilder House Berkshires

Sheffield

Liliana

$182 nightly

Nov 12 - Nov 13

Total with taxes and fees

A covered porch with white railings and rocking chairs.

2. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

$105 nightly

Nov 12 - Nov 13

Total with taxes and fees

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

3. Blackberry River Inn

Norfolk

Melanie

$180 nightly

Nov 12 - Nov 13

Total with taxes and fees

A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.

4. Granville House

Housatonic

Cynthia

$254 nightly

Nov 20 - Nov 21

Total with taxes and fees

5. The Inn at Stockbridge

Stockbridge

Kimberly

$255 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Stockbridge

Philippe

$389 nightly

Dec 12 - Dec 13

Total with taxes and fees

A crowded outdoor event with tents and people gathered in a grassy area.

7. Chambery Inn

Lee

Alexandra

$194 nightly

Nov 22 - Nov 23

Total with taxes and fees

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

8. Devonfield Inn B&B

Lee

Sebastien

$369 nightly

Nov 13 - Nov 14

Total with taxes and fees

A snow-covered outdoor area with a patio, seating, and a covered dining area.

9. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

$178 nightly

Nov 15 - Nov 16

Total with taxes and fees

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

10. Inn at Silver Maple Farm

East Chatham

Linda

$164 nightly

Dec 3 - Dec 4

Total with taxes and fees

A garden with a white gazebo, a brick pathway, and various plants and flowers.

11. Whistler's Inn Bed & Breakfast

Lenox

George

A red building with a sign reading "Shaker Mill Inn."

12. Shaker Mill Inn

West Stockbridge

Mahadeva

$145 nightly

Nov 12 - Nov 13

Total with taxes and fees

A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

13. Inn at Pine Plains

Pine Plains

teresina

$275 nightly

Nov 12 - Nov 13

Total with taxes and fees

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

14. Changing Times Boutique Country Lodging

Craryville

Thomas

$200 nightly

Nov 12 - Nov 13

Total with taxes and fees

A porch with a white railing, a potted plant, and a view of a garden.

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

Lenox

$328 nightly

Nov 15 - Nov 16

Total with taxes and fees

A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

16. Experience Timeless Elegance in The Edith Wharton Room!

Lenox

$295 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

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

Lenox

$310 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Lenox

$295 nightly

Nov 15 - Nov 16

Total with taxes and fees

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

19. Brook Farm Inn

Lenox

Carrie

$170 nightly

Nov 13 - Nov 14

Total with taxes and fees

A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

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

Lenox

$345 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

See all hotels in Sheffield

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

Top reviews in Sheffield

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

Locust Tree Bed and Breakfast LLC

East Canaan

10/10 Excellent

rose

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

The Inn at Stockbridge

Stockbridge

10/10 Excellent

Kevin

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

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

Stockbridge

10/10 Excellent

Charles

Changing Times Boutique Country Lodging

Craryville

10/10 Excellent

Our second time staying here was even more lovely than the first! We brought more family members after our great experience last year. We love the easy check in, cozy comfortable rooms, lots of extras (books and DVDs in the hallway, sweet treats downstairs and in the rooms) and Loretta is the BEST host! She makes an exquisite breakfast and accommodates our early start time. Can’t wait to stay here again.

Kathleen

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

Chambery Inn

Lee

10/10 Excellent

Elaine

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

Inn at Pine Plains

Pine Plains

10/10 Excellent

Kevin

Brook Farm Inn

Lenox

10/10 Excellent

roberta

A two-story house with a front porch, a garage with a red car, and a driveway with a black car.

Jenny's Country Manor

Red Hook

10/10 Excellent

Elyssamay

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 $120 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.

Book Sheffield Bed & Breakfast

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Upfront pricing

Check prices for these dates

Our top choices for Sheffield bed & breakfast

1. Wilder House Berkshires

2. Locust Tree Bed and Breakfast LLC

3. Blackberry River Inn

4. Granville House

5. The Inn at Stockbridge

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

7. Chambery Inn

8. Devonfield Inn B&B

9. The Cornell Inn, Lenox & The Berkshires

10. Inn at Silver Maple Farm

11. Whistler's Inn Bed & Breakfast

12. Shaker Mill Inn

13. Inn at Pine Plains

14. Changing Times Boutique Country Lodging

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

16. Experience Timeless Elegance in The Edith Wharton Room!

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

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

19. Brook Farm Inn

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

Learn more about Sheffield

Top reviews in Sheffield

Wilder House Berkshires

10/10 Excellent

Frequently Asked Questions

What are the most popular Sheffield Bed and Breakfasts?

What is the nightly rate for a Bed and Breakfast in Sheffield?

When is the best time to book a B&B in Sheffield?

What is the difference between a Sheffield B&B and a hotel?

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