Search B&B in Sheffield

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Sheffield

Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated
Wilder House Berkshires
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (37)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
United States
Marina
The price is AED 553
AED 618 total
includes taxes & fees
27 Oct - 28 Oct
Wilder House Berkshires
Garden
Shaker Mill Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (430)
"Very casual and easy check in and out; lovely and substantial breakfast"
United States
Jamie
The price is AED 408
AED 448 total
includes taxes & fees
4 Nov - 5 Nov
Shaker Mill Inn
Library
Blackberry River Inn
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (148)
"A wonderful facility, lovely breakfast and way way more than you would expect in every catagory."
United States
Steve
The price is AED 604
AED 694 total
includes taxes & fees
27 Oct - 28 Oct
Blackberry River Inn
Interior detail
Manor House Inn
Manor House Inn
3.0 star property
9.4 out of 10, Exceptional, (138)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is AED 1,045
AED 1,160 total
includes taxes & fees
17 Nov - 18 Nov
Manor House Inn
Interior
The Red Door B&B
The Red Door B&B
3.0 star property
10.0 out of 10, Exceptional, (5)
"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
The Red Door B&B
Porch
Lakehouse Inn
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (285)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
United States
Roberta
The price is AED 676
AED 793 total
includes taxes & fees
2 Nov - 3 Nov
Lakehouse Inn
Front of property
Chambery Inn
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (370)
"ease of late check in. Super comfortable room."
United States
Mary
Chambery Inn
Property grounds
Whistler's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (499)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
United States
Lisa
The price is AED 422
AED 472 total
includes taxes & fees
30 Oct - 31 Oct
Whistler's Inn Bed & Breakfast
Exterior
The Inn at Stockbridge
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is AED 1,274
AED 1,494 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Stockbridge
Front of property - evening/night
Devonfield Inn B&B
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (132)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Individually decorated, individually furnished, desk, laptop workspace
Granville House
Granville House
3.0 star property
10.0 out of 10, Exceptional, (85)
"Beautiful place! Terri and Terry are the best!"
United States
Stephanie
The price is AED 804
AED 898 total
includes taxes & fees
26 Oct - 27 Oct
Granville House
Terrace/patio
Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (409)
"Peaceful area and great staff; Thank you for the service and experience "
United States
Andre
The price is AED 386
AED 444 total
includes taxes & fees
26 Oct - 27 Oct
Locust Tree Bed and Breakfast LLC
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
The price is AED 762
AED 1,118 total
includes taxes & fees
26 Oct - 27 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AED 469
AED 667 total
includes taxes & fees
26 Oct - 27 Oct
The Cornell Inn, Lenox & The Berkshires
Business center
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
9.2 out of 10, Wonderful, (108)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is AED 1,137
AED 1,375 total
includes taxes & fees
9 Nov - 10 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
33 Main
4.0 star property
10.0 out of 10, Exceptional, (73)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AED 1,689
AED 1,887 total
includes taxes & fees
24 Nov - 25 Nov
33 Main
Aerial view
Inn at Silver Maple Farm
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (97)
"Great stay, comfortable place"
United States
barry
The price is AED 584
AED 654 total
includes taxes & fees
23 Nov - 24 Nov
Inn at Silver Maple Farm
1 bedroom, WiFi, bed sheets
Elegant Carriage House room with a queen bed and private patio.
Elegant Carriage House room with a queen bed and private patio.
The price is AED 821
AED 1,191 total
includes taxes & fees
28 Oct - 29 Oct
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!
Experience Timeless Elegance in The Edith Wharton Room!
The price is AED 762
AED 1,118 total
includes taxes & fees
27 Oct - 28 Oct
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony
Cozy Carriage House room with a double bed and private balcony
The price is AED 879
AED 1,265 total
includes taxes & fees
29 Oct - 30 Oct
Cozy Carriage House room with a double bed and private balcony
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful.."
Steven 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Frequently asked questions

Searching for B&Bs in Sheffield?
If you're looking for something a little more offbeat than the traditional hotel experience, a stay at a bed and breakfast might be the perfect option for your getaway. If your ideal vacation 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 a good option for you?
Every B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook, the little details are what make bed and breakfasts a fun place to get away.
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 décor. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the downtown core. 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 décor. Lakehouse Inn: 14 rooms. 15.7 mi (25.2 km) from the heart of downtown. Enjoy the free full breakfast and deli. Inn at Pine Plains: 8 rooms. Located 17.8 mi (28.6 km) from the core of Sheffield.
When should I 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 temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches 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 might 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?
Planning your excursions in and around Sheffield is easier 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. You can also search 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 to rent a car for your trip.