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

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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

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
$267 nightly
The price is $294
Nov 3 - Nov 4
Total with taxes and fees
Inn on Putney Road
A large, two-story house with a snow-covered driveway and surrounding trees.

2. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (106 reviews)
"Great stay"
United States
Wayne
$301 nightly
The price is $327
Oct 22 - Oct 23
Total with taxes and fees
Chesterfield 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, (362 reviews)
"Beautiful grounds, nice walking trails, comfortable bed, excellent breakfast."
United States
Amy
$146 nightly
The price is $161
Oct 28 - Oct 29
Total with taxes and fees
Colonel Williams Inn
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

4. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (61 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
$89 nightly
The price is $97
Nov 2 - Nov 3
Total with taxes and fees
Four Columns Inn
A blue house with a porch, a sign reading "The One Cat", and a garden with various plants and flowers.

5. 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 One Cat B&B
A wooden table set with plates, cutlery, and a folded napkin.

6. 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
$177 nightly
The price is $192
Oct 25 - Oct 26
Total with taxes and fees
The Carriage Barn Inn
A two-story house with a red door, green shutters, and a snow-covered front yard.

7. Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (188 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
$164 nightly
The price is $173
Nov 1 - Nov 2
Total with taxes and fees
Centennial House
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, (138 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
$82 nightly
The price is $90
Nov 19 - Nov 20
Total with taxes and fees
Deerfield Valley Inn
A bowl of food with bananas and nuts on a plate.

9. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (293 reviews)
"The breakfasts were amazing and the hosts were super kind and helpful!"
United States
gail
$194 nightly
The price is $211
Oct 29 - Oct 30
Total with taxes and fees
Harvest Barn Inn
A porch with a table set for two, a chair, and a potted plant.

10. 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
$315 nightly
The price is $353
Oct 28 - Oct 29
Total with taxes and fees
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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Top Chesterfield Hotel Reviews

Otherland Hotel

Otherland Hotel

8/10 Good
"Great place to stay a night or a couple of days. Very modern amenities. Not your traditional hotel, lots of automation and self service."
Jorge 1-night trip
Posted 1 hour ago
Otherland Hotel

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
1,268
Accommodation
14 B&B
Lowest Price
$90
Highest Price
$353

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 $90 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.
When is the best time to book a Bed & Breakfast in Chesterfield?
The best time to book a B&B in Chesterfield is during the vibrant summer months, particularly in July when the area comes alive with activity. This peak season, which runs from June to August, sees an influx of visitors eager to take advantage of Chesterfield's beautiful outdoor spaces and cultural events. With warm temperatures typically ranging from the mid-60s to low 80s Fahrenheit, it's an ideal time for exploring local parks, enjoying leisurely strolls along the waterfront, or attending lively summer festivals.

July stands out as the most popular month to visit, offering a bustling atmosphere filled with community gatherings and outdoor concerts. Travelers can immerse themselves in the local culture and connect with fellow adventurers, all while basking in the summer sun.

For those looking for a more budget-friendly experience, consider visiting in November. This month offers a quieter ambiance, allowing you to enjoy Chesterfield's charm at a more relaxed pace. The crisp autumn air enhances the beauty of local parks, making it a superb time for scenic walks and cozy evenings at your B&B.
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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