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Compare 33 B&B in Sheffield with updated reviews, rates, and availability.

Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (239)
"Amazing breakfast!"
The price is SAR 526
SAR 616 total
includes taxes & fees
24 Jan - 25 Jan
Lakehouse Inn
The Cornell Inn, Lenox
Exterior

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Great place "
The price is SAR 458
SAR 537 total
includes taxes & fees
12 Jan - 13 Jan
The Cornell Inn, Lenox
Blackberry River Inn
Breakfast meal

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (95)
"Very clean. The host was friendly and attentive. Great complimentary breakfast. Clean,quiet and very comfortable. "
The price is SAR 588
SAR 677 total
includes taxes & fees
14 Jan - 15 Jan
Blackberry River Inn
Wilder House Berkshires
Breakfast meal

Wilder House Berkshires

2.0 star property
10.0 out of 10, Exceptional, (11)
"Such a lovely place! The room was spotless and cozy and comfortable! Will definitely be back for hopefully longer than one evening. Brad was friendly, communicative, and accommodating. "
The price is SAR 509
SAR 568 total
includes taxes & fees
23 Jan - 24 Jan
Wilder House Berkshires
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (362)
"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 SAR 713
SAR 797 total
includes taxes & fees
16 Jan - 17 Jan
Chambery Inn
Granville House
Room

Granville House

3.0 star property
10.0 out of 10, Exceptional, (80)
"Beautiful rooms, wonderful hosts, been here several times and plan to come again. "
The price is SAR 845
SAR 943 total
includes taxes & fees
15 Jan - 16 Jan
Granville House
Inn at Pine Plains
Breakfast area

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (279)
"I wanted to find a nice bed-and-breakfast inn-type place to stay at during a brief trip to upstate New York (Dutchess County). The Inn at Pine Plains receives consistently excellent reviews on Expedia so I decided to follow those recommendations. The good reviews are accurate. Plus, there are at least two excellent world-class restaurants within walking distance. "
The price is SAR 957
SAR 1,073 total
includes taxes & fees
22 Jan - 23 Jan
Inn at Pine Plains
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (405)
"Quaint "
The price is SAR 394
SAR 432 total
includes taxes & fees
13 Jan - 14 Jan
Shaker Mill Inn
Devonfield Inn B&B
Room

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (121)
"Great location "
The price is SAR 1,010
SAR 1,128 total
includes taxes & fees
15 Jan - 16 Jan
Devonfield Inn B&B
33 Main
Room

33 Main

4.0 star property
10.0 out of 10, Exceptional, (69)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is SAR 1,366
SAR 1,526 total
includes taxes & fees
26 Jan - 27 Jan
33 Main
Tanglewood Suites
Property grounds

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is SAR 822
SAR 822 total
includes taxes & fees
12 Jan - 13 Jan
Tanglewood Suites
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (149)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is SAR 698
SAR 780 total
includes taxes & fees
19 Jan - 20 Jan
Brook Farm Inn
Inn at Silver Maple Farm
Front of property

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (80)
"Everything "
The price is SAR 522
SAR 564 total
includes taxes & fees
12 Jan - 13 Jan
Inn at Silver Maple Farm
Locust Tree Bed and Breakfast LLC
Exterior

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (374)
"Very pretty setting and house. Comfortable bed. Nice view Would have liked bottled water available in the room. Breakfast was nice."
The price is SAR 394
SAR 453 total
includes taxes & fees
12 Jan - 13 Jan
Locust Tree Bed and Breakfast LLC
Manor House Inn
Restaurant

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (135)
"A charming old manor from the Gilded Age, thoughtfully updated and modernized without losing the soul of the original home. Incredibly comfortable rooms, inviting common spaces, excellent breakfast, beautiful grounds, and friendly staff. We especially enjoyed the fireplace in our room. Perfect for a romantic getaway, we look forward to visiting again in the future."
Manor House Inn
Jenny's Country Manor
Exterior

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (124)
"The manager was very amenable to changing our room due to a complaint about a problem we had. And was sincerely concerned. They have a very nice light breakfast on Saturday mornings. "
The price is SAR 526
SAR 589 total
includes taxes & fees
16 Jan - 17 Jan
Jenny's Country Manor
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (97)
"Very enjoyable stat."
The Inn at Stockbridge
Whistler's Inn Bed & Breakfast
Interior

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
View from room

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is SAR 1,593
SAR 1,927 total
includes taxes & fees
12 Jan - 13 Jan
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Changing Times Boutique Country Lodging
Front of property

Changing Times Boutique Country Lodging

3.5 star property
10.0 out of 10, Exceptional, (93)
"The stay was great. The host baked delicious muffins for breakfast and everything was clean "
The price is SAR 563
SAR 608 total
includes taxes & fees
12 Jan - 13 Jan
Changing Times Boutique Country Lodging
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
great kitchen for cooking in

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (35)
"We stayed at this home about the same time last year and we were so happy with everything about it, we jumped at the opportunity to stay there again. The house has absolutely everything you'd need and is close to Canaan, CT and Great Barrington, MA and everything the Bershires have to offer. Sabrina is a great host and responded within minutes to any questions I had. We HIGHLY recommend this home."
Cheerful 3-bedroom cottage with woodstove
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (202)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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

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, Bartholomews Cobble and Mount Everett State Reservation 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: The Cornell Inn, Lenox: 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 downtown core. Enjoy the free full breakfast and deli. Blackberry River Inn: 14 rooms. Situated 9.2 mi (14.9 km) from the heart of Sheffield. Enjoy the free cooked breakfast and outdoor pool. Chambery Inn: 9 rooms. 14.7 mi (23.7 km) from the heart of downtown. Enjoy the private yard and deli. Shaker Mill Inn: 9 rooms. Located 15.6 mi (25.1 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, Bartholomews Cobble and Mount Everett State Reservation are some notable spots. You might put Three Mile Pond Wildlife Management Area and Housatonic River 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.