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 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, (416)
"I enjoyed a very comfortable 3 night stay at The Ellery. It was a great home base from which to explore the many fun shops, restaurants and unique vibe of Northampton. My room Was quite comfortable. I will definitely stay there during any future visit."
The price is AED 531
AED 593 total
includes taxes & fees
4 Jul - 5 Jul
The Ellery
Old Mill Inn
Living area
Old Mill Inn
3.0 star property
9.4 out of 10, Exceptional, (443)
"Beautiful place to stay."
The price is AED 733
AED 819 total
includes taxes & fees
24 Jun - 25 Jun
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, (106)
"nice comfortable and funky!"
The price is AED 803
AED 897 total
includes taxes & fees
23 Jun - 24 Jun
The Trail in Adams - Berkshires’ Art Hotel
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Daniel Stebbins House
Exterior
Daniel Stebbins House
3.0 star property
10.0 out of 10, Exceptional, (39)
"The loveliest hosts. "
The price is AED 993
AED 1,049 total
includes taxes & fees
23 Jun - 24 Jun
Daniel Stebbins House
Harbour House Inn
Exterior
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (48)
"Decorations were beautiful, room and bed were so comfortable, hostess and food were wonderful. Brandi was thoughtful in every way possible. Can't go wrong choosing this place over a chain. Love it!"
The price is AED 908
AED 960 total
includes taxes & fees
24 Jun - 25 Jun
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
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.

Other property types in Chesterfield

Cozy apartment located in quiet Williamsburg
Exterior
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, (35)
"Very clean and nice apartment in a pleasant little city."
The price is AED 551
AED 955 total
includes taxes & fees
23 Jun - 24 Jun
Cozy apartment located in quiet Williamsburg
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
The Creation Station is a cozy place so make yourself at home.
Exterior
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (52)
"Wonderful place to stay, had a great time lots of instruments to try, had lots of space to spread out and hangout, the hot tub was very nice and clean. Overall had a fantastic stay the lighted walkway is amazing! All the amenities available where also great, Jon was a great host and we had a great time speaking with him!"
The price is AED 661
AED 1,030 total
includes taxes & fees
2 Jul - 3 Jul
The Creation Station is a cozy place so make yourself at home.
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.

Recent reviews of Chesterfield hotels
Expedia verified reviews

Howard Johnson by Wyndham Amherst Hadley

Howard Johnson by Wyndham Amherst Hadley

5/5 Excellent
"The room was clean and the hospitality was fabulous!"
A verified traveler from Sarasota stayed at Howard Johnson by Wyndham Amherst Hadley
Posted 1 day ago
Howard Johnson by Wyndham Amherst Hadley