Search B&B in Chesterfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Mar - 8 Mar
In two weeks
13 Mar - 15 Mar
In one month
27 Mar - 29 Mar
In two months
24 Apr - 26 Apr

Our top choices for Chesterfield bed & breakfast

Deluxe Room, 1 King Bed | Hypo-allergenic bedding, individually decorated, individually furnished

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
9.8 out of 10, Exceptional, (104 reviews)
"Enjoyable stay with a warm environment. Enjoyed the breakfast which was well prepared based on my order choice and request. Would stay again!"
United States
Karri
Black Walnut Inn
Exterior

Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (503 reviews)
"Clean facilities, beautiful aesthetic, attentive staff, quiet area, tasty breakfast."
United States
Scarlett
The price is SAR 1,215
SAR 1,357 total
includes taxes & fees
28 Feb - 1 Mar
Old Mill Inn
Exterior

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is SAR 844
SAR 892 total
includes taxes & fees
28 Feb - 1 Mar
UU Rowe Camp and Conference Center
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (144 reviews)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is SAR 652
SAR 728 total
includes taxes & fees
1 Mar - 2 Mar
The Trail in Adams - Berkshires’ Art Hotel
1 bedroom, WiFi

Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
The price is SAR 431
SAR 511 total
includes taxes & fees
2 Mar - 3 Mar
Cozy Farmhouse Retreat - Ram Dass Room
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is SAR 894
SAR 945 total
includes taxes & fees
9 Mar - 10 Mar
Harbour House Inn
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.
View all properties

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

The Ellery

The Ellery

10/10 Excellent
"What a lovely hotel - kind staff, hearty breakfast, beautiful place - would stay again. Only qualm is that the heater is quite loud."
Christa 2-night trip
Posted 8 hours ago
The Ellery

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: Black Walnut Inn: 10 rooms. 15.8 mi (25.4 km) from the heart of Chesterfield. Enjoy the free full breakfast and unique décor. Old Mill Inn: 12 rooms. 11.9 mi (19.1 km) from the downtown core. Enjoy the deli and unique décor.
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 Westfield River and Chesterfield Public Library 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.