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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Lovely, comfortable B&B with a nice feel. We plan to return."
The price is HK$962
HK$1,378 total
includes taxes & fees
20 Apr - 21 Apr
The Cornell Inn, Lenox & The Berkshires
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (255)
"We had a great stay at The Lakehouse Inn. Upon arrival we were greeted with a beverage and brownies. Our room was lovely, the new gas fireplace was a bonus. And the breakfast was out of this world! Service was fantastic from everyone involved, especially our breakfast server Kathleen. We would definitely recommend a stay here."
Lakehouse Inn
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (99)
"So charming, friendly staff, perfectly comfortable. We had the best stay. "
The price is HK$1,290
HK$1,484 total
includes taxes & fees
5 May - 6 May
Blackberry River Inn
Wilder House Berkshires
Premium bedding, individually decorated, individually furnished

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (20)
"Bert was great - he really tried to help after the Expedia website (and app) made it impossible for me to cancel my trip (my wife and I came down with Influenza A). There was little he could do as I had booked through Expedia. I ended up paying full price and am finding it impossible to communicate with Expedia..."
The price is HK$1,188
HK$1,327 total
includes taxes & fees
27 Apr - 28 Apr
Wilder House Berkshires
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (377)
"The host Heidi was friendly and fun to talk with at breakfast (I was travelling alone). She knows a lot about the area and history which was nice to hear. The house was quiet and clean and I'd stay here again."
The price is HK$815
HK$937 total
includes taxes & fees
29 Apr - 30 Apr
Locust Tree Bed and Breakfast LLC
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (409)
"Beautiful room, very clean. breakfast was not what i was expecting, walk way from parking lot covered with ice and snow, very dangerous to walk, needs to be cleaned or at least put some salt on the ground. other then that everything was excellent. will stay again"
The price is HK$1,125
HK$1,234 total
includes taxes & fees
27 Apr - 28 Apr
Shaker Mill Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"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 HK$1,863
HK$2,081 total
includes taxes & fees
18 Apr - 19 Apr
Chambery Inn
33 Main
Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"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 HK$3,045
HK$3,401 total
includes taxes & fees
22 Apr - 23 Apr
33 Main
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (281)
"A charming inn with nice rooms upstairs and downstairs and a variety of cozy public rooms on the ground floor. Very nice, serve-yourself continental breakfast, although no hot food (at least not on our weekend). Well-located near the center of Pine Plains."
The price is HK$1,979
HK$2,239 total
includes taxes & fees
20 Apr - 21 Apr
Inn at Pine Plains
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (151)
"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 HK$1,351
HK$1,509 total
includes taxes & fees
18 Apr - 19 Apr
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, (124)
"Very enjoyable comfortable stay"
The price is HK$1,933
HK$2,159 total
includes taxes & fees
19 Apr - 20 Apr
Devonfield Inn B&B
Whistler's Inn Bed & Breakfast
Property grounds

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...
The price is HK$1,270
HK$1,566 total
includes taxes & fees
1 May - 2 May
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

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 HK$3,292
HK$3,982 total
includes taxes & fees
30 Apr - 1 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Jenny's Country Manor
Exterior

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (126)
"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 HK$1,086
HK$1,229 total
includes taxes & fees
28 Apr - 29 Apr
Jenny's Country Manor
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (84)
"Here’s the review translated into English: ⭐⭐⭐⭐⭐ (5 stars – if there were 8, we’d give 8!) We had an unforgettable stay at the Maple Farm Hotel! The accommodation is decorated with incredible attention to detail and taste – the warm wood, stylish furniture, and countless charming little touches create a beautiful, natural atmosphere. In the mornings, we were awakened by the cheerful chirping of birds, which was simply magical. We especially loved the cozy hours by the fireplace and the...
The price is HK$1,156
HK$1,248 total
includes taxes & fees
27 Apr - 28 Apr
Inn at Silver Maple Farm
Manor House Inn
Garden

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
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"
The Inn at Stockbridge
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Phenomenal hospitality, eclectic decor, luxurious sleep - we have been raving about our stay and will definitely be back!"
The price is HK$1,545
HK$1,725 total
includes taxes & fees
20 Apr - 21 Apr
Granville House
Tanglewood Suites
Premium bedding, iron/ironing board, free WiFi, bed sheets

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 HK$1,699
HK$1,699 total
includes taxes & fees
30 Apr - 1 May
Tanglewood Suites
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
The price is HK$3,297
HK$3,617 total
includes taxes & fees
30 Apr - 1 May
Inn at Kenmore Hall
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

Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
The price is HK$3,918
HK$6,733 total
includes taxes & fees
30 Apr - 1 May
Guesthouse Cabin vacation rentals in Berkshire County
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is HK$846
HK$1,118 total
includes taxes & fees
21 Apr - 22 Apr
Deluxe Queen Room with 2 Queen Beds
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 quirkier than your standard hotel, a stay at a bed and breakfast could be the perfect alternative for your holiday. If your ideal holiday to Sheffield includes spending lots of time outside, Mount Everett State Reservation and Thom Reed UFO Monument Park are good spots to enjoy the scenery.
How do you know if a B&B is the best choice for you?
B&Bs all have a unique charm — whether it’s a cosy reading space or a beautiful dining room, the little details are what make bed and breakfasts the perfect escape.
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 decor. The Cornell Inn, Lenox & The Berkshires: 18.1 mi (29.1 km) from the city centre. Enjoy the free full breakfast and unique decor. Locust Tree Bed and Breakfast LLC: 7 rooms. Situated 6.8 mi (11 km) from the heart of Sheffield. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the city centre. Enjoy the free cooked breakfast and outdoor pool. Chambery Inn: 9 rooms. Located 14.7 mi (23.7 km) from the core of Sheffield. Enjoy the private garden and snack bar/deli.
What's the best time of year to 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 temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Sheffield?
When you want to spend some time in the great outdoors, Housatonic River and Mount Everett State Reservation are some notable spots. You should put Magnolia Bluffs Casino and Three Mile Pond Wildlife Management Area on your list if you want to see more of the area.
How can I get to and around Sheffield?
Mapping out your trip in and around Sheffield is easy 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. Otherwise, look 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 a rental car for your journey.