Search B&B in Chesterfield

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 7 B&B in Chesterfield with updated reviews, rates, and availability.

The Ellery
Exterior

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (538)
"Perfect."
The price is SAR 522
SAR 583 total
includes taxes & fees
16 Dec - 17 Dec
The Ellery
Black Walnut Inn
Front of property

Black Walnut Inn

2.0 star property
9.8 out of 10, Exceptional, (34)
"Lovely experience! Our room was spacious and cozy. Delicious breakfast and nice people."
The price is SAR 674
SAR 753 total
includes taxes & fees
11 Dec - 12 Dec
Black Walnut Inn
Old Mill Inn
Living area

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (464)
"While we only stayed at The Old Mill for one night we enjoyed the handsome and very comfortable room (Waterfall) and the view of the waterfall and railroad bridge and would love to come back and stay longer - and try the breakfast choices (base on the aromas coming from the tavern in the morning). The staff was pleasant and helpful. "
The price is SAR 712
SAR 795 total
includes taxes & fees
3 Dec - 4 Dec
Old Mill Inn
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (123)
"Stayed only one night Very cosy, quiet place "
The price is SAR 605
SAR 676 total
includes taxes & fees
3 Dec - 4 Dec
The Trail in Adams - Berkshires’ Art Hotel
Daniel Stebbins House
Exterior

Daniel Stebbins House

3.0 star property
10.0 out of 10, Exceptional, (45)
"What is not to love about being welcomed into Richard and Ruth’s home. They are wonderful hosts and spent hours talking to us both during our stay. The house is an amazing building and learning about its history was wonderful. We walked into the tiny town and got some dinner, lovely options available. We can not wait to visit again and will be recommending anyone travelling around this area should certainly book a stay."
The price is SAR 1,015
SAR 1,072 total
includes taxes & fees
2 Dec - 3 Dec
Daniel Stebbins House
Harbour House Inn
Room

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is SAR 965
SAR 1,020 total
includes taxes & fees
4 Dec - 5 Dec
Harbour House Inn
The Red Door B&B
Exterior

The Red Door B&B

3.0 star property
10.0 out of 10, Exceptional, (5)
"We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "
The Red Door B&B
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.
Don't see what you're looking for?
See all available properties in Chesterfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chesterfield

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is SAR 548
SAR 839 total
includes taxes & fees
2 Dec - 3 Dec
Berkshire Village Carriage House - Super Private!!
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake
Pristine Home In Becket Woods

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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 Chesterfield?
If you want to find an accommodation with a small number of rooms and a cozy environment, a B&B might be a great fit for your trip to Chesterfield. While you’re here, you can get to know Chesterfield by exploring its natural beauty. Consider a stop by Chesterfield Gorge and Knightville Dam & Reservation.
How do you know if a B&B is the best choice for your stay?
With attentive service, an atmosphere suited to mingling with other guests, and of course a scrumptious breakfast, B&Bs provide a one-of-a-kind setting.
What are the top B&Bs in Chesterfield?
Here are some B&Bs in the surrounding area: The Ellery: 11 mi (17.7 km) from the heart of Chesterfield.Old Mill Inn: 12 rooms. 11.9 mi (19.1 km) from the downtown core. Enjoy the deli and unique décor. Black Walnut Inn: 10 rooms. Situated 15.8 mi (25.4 km) from the heart of Chesterfield. Enjoy the free full breakfast and unique décor. Daniel Stebbins House: 5 rooms. Located 16.3 mi (26.3 km) from the core of Chesterfield. Enjoy the designer toiletries and arcade game room.
What's the best time of year to stay at a B&B in Chesterfield?
When you’re dreaming of a trip to Chesterfield, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chesterfield are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What is there to do in Chesterfield?
Spend some time exploring Chesterfield Gorge and Knightville Dam & Reservation if you’re hoping to see some of the area’s natural features. You might put Chesterfield Town Hall and Westfield River on your list if you want to see more of the area.
How can I get to and around Chesterfield?
Planning your excursions in and around Chesterfield is easier with these transportation options. Fly into Westfield, MA (BAF-Barnes Municipal), which is located 16.6 mi (26.8 km) away from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 23.2 mi (37.3 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.