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Check prices for these dates

Next weekend
26 Sep - 28 Sep
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

B&B in Sheffield

Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (403)
"Peaceful area and great staff; Thank you for the service and experience "
The price is SAR 394
SAR 453 total
includes taxes & fees
16 Sep - 17 Sep
Locust Tree Bed and Breakfast LLC
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (135)
"Vintage antique home. Close to road, but was quiet at night."
The price is SAR 617
SAR 709 total
includes taxes & fees
16 Sep - 17 Sep
Blackberry River Inn
Wilder House Berkshires
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.8 out of 10, Exceptional, (31)
"Beautiful and very comfortable house. Our hosts were always friendly and accessible, breakfast was delicious!"
The price is SAR 741
SAR 828 total
includes taxes & fees
13 Oct - 14 Oct
Wilder House Berkshires
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is SAR 437
SAR 635 total
includes taxes & fees
22 Sep - 23 Sep
The Cornell Inn, Lenox & The Berkshires
Manor House Inn
Interior detail

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (137)
"Excellent bed and breakfast, room was clean and comfortable."
Manor House Inn
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (280)
"A great getaway! Everything was excellent!"
The price is SAR 583
SAR 684 total
includes taxes & fees
17 Sep - 18 Sep
Lakehouse Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
Chambery Inn
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (425)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is SAR 680
SAR 746 total
includes taxes & fees
21 Sep - 22 Sep
Shaker Mill Inn
Granville House
Individually decorated, individually furnished, desk, laptop workspace

Granville House

3.0 star property
10.0 out of 10, Exceptional, (85)
"Beautiful place! Terri and Terry are the best!"
The price is SAR 1,107
SAR 1,236 total
includes taxes & fees
15 Oct - 16 Oct
Granville House
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (160)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (129)
"The inn has an excellent location and amenities."
Devonfield Inn B&B
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The price is SAR 1,436
SAR 1,684 total
includes taxes & fees
21 Sep - 22 Sep
The Inn at Stockbridge
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (492)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
The price is SAR 544
SAR 608 total
includes taxes & fees
16 Sep - 17 Sep
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is SAR 1,161
SAR 1,405 total
includes taxes & fees
30 Sep - 1 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (71)
"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 2,299
SAR 2,568 total
includes taxes & fees
8 Oct - 9 Oct
33 Main
Tanglewood Suites
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

Tanglewood Suites

2.5 star property
6.4 out of 10, (22)
"This is a VRBO !!! Not a Bed & Breakfast. Not on Main Street in Stockbridge! Not called the Tanglewood Suites. Total misrepresentation. Cash only payments!!?!! Lousy old croissants and homemade yogurt with no sealed package or date. Homeowner called repeatedly demanding an arrival time!!! Stay elsewhere!"
The price is SAR 1,009
SAR 1,009 total
includes taxes & fees
22 Sep - 23 Sep
Tanglewood Suites
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (94)
"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "
The price is SAR 747
SAR 836 total
includes taxes & fees
16 Sep - 17 Sep
Inn at Silver Maple Farm
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (293)
"Beautiful place. Accomadating staff. A lovely place to stay"
Inn at Pine Plains
Jenny's Country Manor
Exterior

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (130)
"Cool place in the Catskills! Under some renovations but well worth the stop. Big rooms. Comfy beds. Close to so much!"
The price is SAR 525
SAR 594 total
includes taxes & fees
16 Sep - 17 Sep
Jenny's Country Manor
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 Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Lovely clean hotel with great breakfast. "
Linda 1-night trip
Posted 6 days ago
The Yankee, Trademark Collection by Wyndham

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. Locust Tree Bed and Breakfast LLC: 7 rooms. 6.8 mi (11 km) from the heart of downtown.
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.