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, (495)
"Well located, comfortable, but a bit loud on the first floor."
The price is SAR 548
SAR 612 total
includes taxes & fees
1 Oct - 2 Oct
The Ellery
Black Walnut Inn
Front of property
Black Walnut Inn
2.0 star property
10.0 out of 10, Exceptional, (14)
"There is a good feeling and homey atmosphere. "
The price is SAR 674
SAR 753 total
includes taxes & fees
24 Sep - 25 Sep
Black Walnut Inn
Old Mill Inn
Living area
Old Mill Inn
3.0 star property
9.4 out of 10, Exceptional, (461)
"Beautiful New England inn set on old mill and factory, perfectly restored. Our room # had outstanding view of stream and waterfall. Cafe offer great morning breakfast options. A great place for a quiet stay. "
The price is SAR 734
SAR 820 total
includes taxes & fees
30 Sep - 1 Oct
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, (117)
"Interior was fine. Area did not seem safe to me. The bathroom looks nice but not very functional. "
The price is SAR 680
SAR 760 total
includes taxes & fees
24 Sep - 25 Sep
The Trail in Adams - Berkshires’ Art Hotel
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 928
SAR 981 total
includes taxes & fees
24 Sep - 25 Sep
Harbour House Inn
Daniel Stebbins House
Exterior
Daniel Stebbins House
3.0 star property
10.0 out of 10, Exceptional, (41)
"Richard and Ruth are wonderful hosts in their beautiful historic inn. Their kindness made it a bit easier to say goodbye to our daughter for her first year of college. The rooms were perfectly appointed and the home was clean and the attention to detail was impressive. I look forward to returning! "
The price is SAR 1,014
SAR 1,072 total
includes taxes & fees
30 Sep - 1 Oct
Daniel Stebbins House
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
Don't see what you're looking for?
See all available properties in Chesterfield
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.
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

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Lake-we provide kayaks and a canoe!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (205)
"My stay was shorter than I had planned but the few days I was here was so relaxing. First of all, the bed is so comfortable, I slept like a baby. Very quiet area. Nice to walk around with my dogs and explore. The cottage was nicely outfitted with any needs you might have. Beautiful time of year to stay here! I cannot wait to go back. I also want to say I appreciate that they allowed my two dogs. My dogs are very well behaved, and I travel with them quite often. Not all places allow this, so I...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Cozy apartment located in quiet Williamsburg
Exterior
Cozy apartment located in quiet Williamsburg
9.6 out of 10, Exceptional, (41)
"Property was as advertised. Easy to get in and was exactly what we were looking for. "
The price is SAR 563
SAR 972 total
includes taxes & fees
24 Sep - 25 Sep
Cozy apartment located in quiet Williamsburg
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!
Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
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. If your ideal vacation to Chesterfield includes spending lots of time outside, Chesterfield Gorge is a good spot to enjoy the scenery.
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'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 April, with each month seeing an average of 7 inches of snowfall.
What is there to do in Chesterfield?
Spend some time exploring Chesterfield Gorge and Westfield River if you’re hoping to see some of the area’s natural features. You might also consider a trip to sites like Look Memorial Park or Smith College Botanic Garden if you have time 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.