Find a Bed and Breakfast in Chesterfield from CA $64

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Chesterfield bed & breakfast

A large, two-story house with a snow-covered driveway and surrounding trees.

1. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.4 out of 10, Exceptional, (106 reviews)
"Great stay"
United States
Wayne
The price is CA $425
CA $462 total
includes taxes & fees
Nov 11 - Nov 12
Chesterfield Inn
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

2. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (61 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
The price is CA $377
CA $415 total
includes taxes & fees
Nov 10 - Nov 11
Inn on Putney Road
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

3. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (63 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is CA $210
CA $229 total
includes taxes & fees
Nov 23 - Nov 24
Four Columns Inn
A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

4. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (177 reviews)
"Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++"
United States
Richard
The price is CA $177
CA $192 total
includes taxes & fees
Nov 12 - Nov 13
The Carriage Barn Inn
A room with two single beds, a desk, and a radiator.

5. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (363 reviews)
"Beautiful grounds, nice walking trails, comfortable bed, excellent breakfast."
United States
Amy
The price is CA $245
CA $269 total
includes taxes & fees
Nov 23 - Nov 24
Colonel Williams Inn
A two-story house with a red door, green shutters, and a snow-covered front yard.

6. Centennial House

Centennial House
3.5 star property
Northfield
9.8 out of 10, Exceptional, (194 reviews)
"Excellent host making us feel very welcome. Very nice room and really lovely breakfast. Would certainly stay again if we are in the area."
United Kingdom
Alan
The price is CA $246
CA $260 total
includes taxes & fees
Nov 10 - Nov 11
Centennial House
A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

7. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (296 reviews)
"Staff was excellent and river views were amazing"
United States
John
The price is CA $223
CA $243 total
includes taxes & fees
Nov 27 - Nov 28
Harvest Barn Inn
A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

8. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (140 reviews)
"A very quaint, cozy inn set in West Dover, Vermont. We had a small room but it was clean and comfortable. We didn't choose to order breakfast while we were there but it smelled wonderful! Oz, the host, was professional, pleasant, and helpful."
United States
Ted
The price is CA $65
CA $110 total
includes taxes & fees
Nov 24 - Nov 25
Deerfield Valley Inn
A porch with a table set for two, a chair, and a potted plant.

9. Private bedroom in the Green River Bridge Inn. A full breakfast is included.

Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Guilford
2.0 out of 10, (1 review)
The price is CA $389
CA $451 total
includes taxes & fees
Nov 16 - Nov 17
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
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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Learn more about Chesterfield

Tucked along the Connecticut River, this charming New England town offers peaceful kayaking and hiking trails through Pisgah State Park. Spend summer days swimming at Spofford Lake, where local families gather for picnics and the annual Old Home Day celebrations.

See all hotels in Chesterfield
A U.S. Post Office in Chesterfield, N.H. with stone walls and green shutters.

Top reviews in Chesterfield

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.
Four Columns Inn

Four Columns Inn

Four Columns Inn
Newfane

10/10 Excellent

Great place to stay. People were Friendly and the service was great. The pizza was great and the service was outstanding.
Canada
Marie-Christine
Reviewed September 29, 2025
Four Columns Inn

Frequently Asked Questions

What is the nightly rate for a B&B in Chesterfield?

Prices for B&Bs in Chesterfield often vary, but you can find a great deal from CA $64 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.

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