A rural landscape with a grassy field, a dirt path, and a hill covered with autumn-colored trees.

Find a Bed and Breakfast in Chesterfield from CA $165

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Check prices for these dates

Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27
In one month
Oct 9 - Oct 11
In two months
Nov 6 - Nov 8

Our top choices for Chesterfield bed & breakfast

A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

1. 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 $408
CA $449 total
includes taxes & fees
Sep 8 - Sep 9
Inn on Putney Road
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

2. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (54 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is CA $197
CA $215 total
includes taxes & fees
Sep 13 - Sep 14
Four Columns Inn
A large white building with a stone wall and a lawn covered in fallen leaves.

3. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (359 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is CA $209
CA $230 total
includes taxes & fees
Sep 22 - Sep 23
Colonel Williams Inn
A blue house with a porch, a sign reading "The One Cat", and a garden with various plants and flowers.

4. The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.8 out of 10, Exceptional, (81 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is CA $407
CA $447 total
includes taxes & fees
Sep 28 - Sep 29
The One Cat B&B
A wooden table set with plates, cutlery, and a folded napkin.

5. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (176 reviews)
"Perfectly clean and quaint. Friendly owner, great location"
United States
Jonathan
The price is CA $209
CA $227 total
includes taxes & fees
Sep 15 - Sep 16
The Carriage Barn 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
9.6 out of 10, Exceptional, (177 reviews)
"David was incredibly hospitable. I thoroughly enjoyed my stay. "
United States
Amy
The price is CA $243
CA $257 total
includes taxes & fees
Sep 15 - Sep 16
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, (279 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
The price is CA $219
CA $239 total
includes taxes & fees
Sep 12 - Sep 13
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, (132 reviews)
"Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place"
United States
Patrick
The price is CA $116
CA $165 total
includes taxes & fees
Sep 22 - Sep 23
Deerfield Valley Inn
A table with various food items and a bottle of wine, overlooking a lush garden.

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
The price is CA $381
CA $479 total
includes taxes & fees
Sep 14 - Sep 15
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.

10. Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (45 reviews)
"The view of mountains id stunning, as is the aroma of fresh air and the enchanting songbirds. We had a great time in the small but adequate swimming pool. It is easy to miss the turn onto Laurence Lane, so it would be good if a sign were to be installed there."
United States
Nadine
The price is CA $322
CA $351 total
includes taxes & fees
Sep 22 - Sep 23
Windham Hill 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

Econo Lodge Brattleboro South

Econo Lodge Brattleboro South

10/10 Excellent
"We were pleasantly surprised by this property! The staff is super helpful and friendly, the breakfast just perfect and the room is very very clean. Would definitely stay here again!"
Stacy 1-night trip
Posted 23 hours ago
Econo Lodge Brattleboro South

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
1,258
Accommodation
14 B&B
Lowest Price
CA $165
Highest Price
CA $449

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 $165 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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