Default HTG hotel image

Find a Bed and Breakfast in Chesterfield from CA $157

  • 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
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
The price is CA $216
CA $241 total
includes taxes & fees
Nov 16 - Nov 17
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, (161 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
The price is CA $240
CA $268 total
includes taxes & fees
Nov 18 - Nov 19
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
The price is CA $190
CA $200 total
includes taxes & fees
Oct 24 - Oct 25
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
The price is CA $226
CA $252 total
includes taxes & fees
Nov 18 - Nov 19
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
The price is CA $382
CA $427 total
includes taxes & fees
Oct 19 - Oct 20
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 traveller
The price is CA $248
CA $396 total
includes taxes & fees
Oct 26 - Oct 27
The Red Door B&B
Room

7. Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
The price is CA $127
CA $157 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Farmhouse Retreat - Ram Dass Room
Room

8. Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
The price is CA $184
CA $214 total
includes taxes & fees
Oct 19 - Oct 20
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.
The price is CA $184
CA $214 total
includes taxes & fees
Oct 19 - Oct 20
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
The price is CA $359
CA $379 total
includes taxes & fees
Oct 22 - Oct 23
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
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

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"Clean and great service!!"
Rene 1-night trip
Posted 2 hours ago
Tru by Hilton Chicopee Springfield

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
987
Accommodation
18 B&B
Lowest Price
CA $157
Highest Price
CA $427

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Chesterfield?
Prices for B&Bs in Chesterfield often vary, but you can find a great deal from CA $157 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chesterfield B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
What is the difference between a Chesterfield Bed and Breakfast and a hotel?
Every Chesterfield B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chesterfield B&Bs.

Explore a world of travel with Expedia