Bed and Breakfast in Sheffield

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Check prices for these dates

Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec

Featured B&B in Sheffield

Wilder House Berkshires
Wilder House Berkshires Room 3

Wilder House Berkshires

2.0 star property
9.8 out of 10, Exceptional, (35)
"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."
The price is NZ$310
includes taxes & fees
3 Nov - 4 Nov
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, (406)
"Peaceful area and great staff; Thank you for the service and experience "
The price is NZ$208
includes taxes & fees
13 Oct - 14 Oct
Locust Tree Bed and Breakfast LLC
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (142)
"Loved everything especially Lucas and Joe💟☮️"
The price is NZ$326
includes taxes & fees
14 Oct - 15 Oct
Blackberry River Inn
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, (1005)
"Very friendly staff. "
The price is NZ$314
includes taxes & fees
28 Oct - 29 Oct
The Cornell Inn, Lenox & The Berkshires
Manor House Inn
Interior detail

Manor House Inn

3.0 star property
9.4 out of 10, Exceptional, (138)
"Excellent bed and breakfast, room was clean and comfortable."
The price is NZ$575
includes taxes & fees
14 Oct - 15 Oct
Manor House Inn
Lakehouse Inn
Porch

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. "
The price is NZ$355
includes taxes & fees
2 Nov - 3 Nov
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
The Red Door B&B
Interior

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."
The Red Door B&B
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 NZ$422
includes taxes & fees
15 Oct - 16 Oct
Granville House
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft)

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (428)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is NZ$245
includes taxes & fees
3 Nov - 4 Nov
Shaker Mill 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 NZ$748
includes taxes & fees
2 Nov - 3 Nov
The Inn at Stockbridge
33 Main
Luxury Room, 1 King Bed, Bathtub

33 Main

4.0 star property
10.0 out of 10, Exceptional, (72)
"The Inn is beautiful. Decor and rooms are well appointed. Breakfast was delicious and served in beautiful rooms. The staff is friendly and welcoming. Our room was on the first floor, and although it was pretty, it was noisy in the morning (starting very early) as it was close to the kitchen/breakfast dining."
The price is NZ$706
includes taxes & fees
5 Nov - 6 Nov
33 Main
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (495)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
The price is NZ$274
includes taxes & fees
2 Nov - 3 Nov
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

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 NZ$645
includes taxes & fees
27 Oct - 28 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (95)
"Great stay, comfortable place"
The price is NZ$365
includes taxes & fees
2 Nov - 3 Nov
Inn at Silver Maple Farm
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is NZ$518
includes taxes & fees
28 Oct - 29 Oct
Experience Timeless Elegance in The Edith Wharton Room!
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (295)
"Beautiful place. Accomadating staff. A lovely place to stay"
The price is NZ$536
includes taxes & fees
12 Oct - 13 Oct
Inn at Pine Plains
Jenny's Country Manor
Exterior

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (133)
"Cool place in the Catskills! Under some renovations but well worth the stop. Big rooms. Comfy beds. Close to so much!"
The price is NZ$273
includes taxes & fees
13 Oct - 14 Oct
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

Quality Inn

Quality Inn

10/10 Excellent
"Staff was very friendly. Room was ok, but the bathroom tub, floor, and walls needed more attention. Microwave and fridge in room. Perfect location for taking in shows at the beautiful Mahaiwe theatre, as well as browsing Main St shoppes and restaurants. Close driving distance to area attractions."
Petri 2-night trip
Posted 1 day ago
Quality Inn

Find out more about Sheffield

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,686
Accommodation
41 B&B
Lowest Price
NZ$208
Highest Price
NZ$748

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, Thom Reed UFO Monument Park and Bartholomews Cobble 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. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the city centre. 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 decor. Locust Tree Bed and Breakfast LLC: 7 rooms. 6.8 mi (11 km) from the city centre. Lakehouse Inn: 14 rooms. Located 15.7 mi (25.2 km) from the core of Sheffield. Enjoy the free full breakfast 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 Thom Reed UFO Monument Park 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.

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