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

Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

Our top choices for Chesterfield bed & breakfast

A view of a red building by a waterway through a window.

1. Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (547 reviews)
"This place is all about the location and quality rooms with a view. Both excellent. Made for a perfect stopover on our New England Fall Foliage trip."
United States
John
$155 nightly
The price is $173
Oct 29 - Oct 30
Total with taxes and fees
Old Mill Inn
A room with a bed, a sofa, a coffee table, and a television.

2. Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
9.8 out of 10, Exceptional, (160 reviews)
"A great old historic B&B in a beautiful neighborhood with an extremely helpful staff who even made breakfast to order for me. I enjoyed it and the area so much that I stayed an extra night."
United States
Douglas
$179 nightly
The price is $200
Nov 18 - Nov 19
Total with taxes and fees
Black Walnut Inn
A house with a chimney, surrounded by trees with autumn foliage.

3. 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
$149 nightly
The price is $157
Oct 24 - Oct 25
Total with taxes and fees
UU Rowe Camp and Conference Center
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

4. 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, (157 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
$160 nightly
The price is $179
Nov 18 - Nov 19
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
A two-story white house with a green door, white picket fence, and white flowering bushes.

5. Daniel Stebbins House

Daniel Stebbins House
3.0 star property
South Hadley
10.0 out of 10, Exceptional, (56 reviews)
"Great set up and perfect for visiting Mt Holyoke"
United States
David
$270 nightly
The price is $302
Oct 19 - Oct 20
Total with taxes and fees
Daniel Stebbins House
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

6. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveler
$270 nightly
The price is $302
Oct 26 - Oct 27
Total with taxes and fees
The Red Door B&B
Room

7. Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
$110 nightly
The price is $111
Oct 19 - Oct 20
Total with taxes and fees
Cozy Farmhouse Retreat - Ram Dass Room
Room

8. Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
$150 nightly
The price is $151
Oct 19 - Oct 20
Total with taxes and fees
Cozy Retreat in historic Farmhouse - Tranquility Room
Room

9. 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
Oct 19 - Oct 20
Total with taxes and fees
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

10. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.6 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
$233 nightly
The price is $247
Nov 17 - Nov 18
Total with taxes and fees
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.
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Top Chesterfield Hotel Reviews

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst

10/10 Excellent
"Excellent breakfast good variety of protein and fruits"
Gerry 2-night trip
Posted 3 hours ago
Comfort Inn & Suites Hadley - Amherst

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
826
Accommodation
18 B&B
Lowest Price
$111
Highest Price
$302

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: Old Mill Inn: 12 rooms. 11.9 mi (19.1 km) from the heart of Chesterfield. Enjoy the deli and unique décor. Black Walnut Inn: 10 rooms. 15.8 mi (25.4 km) from the downtown core. 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 Chesterfield Gorge Reservation if you're hoping to see some of the area's natural features. You might put Chesterfield Public Library and Chesterfield Town Hall 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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