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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Jan 30 - Feb 1
In two weeks
Feb 6 - Feb 8
In one month
Feb 20 - Feb 22
In two months
Mar 20 - Mar 22

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
10.0 out of 10, Exceptional, (99 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
$175 nightly
The price is $196
Jan 28 - Jan 29
Total with taxes and fees
Black Walnut Inn
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
$206 nightly
The price is $218
Feb 3 - Feb 4
Total with taxes and fees
Harbour House Inn
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
$174 nightly
The price is $194
Jan 21 - Jan 22
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
2 bedrooms, WiFi

Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
Rowe
10.0 out of 10, Exceptional, (2 reviews)
"The piano, large spaces, and fireplace were all much appreciated."
United States
Benjamin B.
$150 nightly
The price is $151
Jan 21 - Jan 22
Total with taxes and fees
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
Exterior

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
$149 nightly
The price is $157
Jan 21 - Jan 22
Total with taxes and fees
UU Rowe Camp and Conference Center
1 bedroom, WiFi

Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
$135 nightly
The price is $136
Jan 21 - Jan 22
Total with taxes and fees
Cozy Farmhouse Retreat - Ram Dass Room
1 bedroom, WiFi

Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
$150 nightly
The price is $151
Jan 21 - Jan 22
Total with taxes and fees
Cozy Retreat in historic Farmhouse - Tranquility Room
Exterior

Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (501 reviews)
"Loved our stay! "
United States
Jay
$199 nightly
The price is $223
Jan 29 - Jan 30
Total with taxes and fees
Old Mill 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.
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Top Chesterfield Hotel Reviews

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"Clean, cool rooms. Staff was very welcoming & professional."
David 2-night trip
Posted 1 day ago
Blue – A Modern Hotel, an Ascend Collection Hotel

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
698
Accommodation
8 B&B
Lowest Price
$157
Highest Price
$223

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. Daniel Stebbins House: 5 rooms. 16.3 mi (26.3 km) from the heart of downtown. 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 Chesterfield Gorge 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.

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