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Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

B&B in Chesterfield

Porch
Harvest Barn Inn

Harvest Barn Inn

3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (243)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
$137 nightly
The price is $150
Nov 11 - Nov 12
Total with taxes and fees
Harvest Barn Inn
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

3.0 star property
Keene
9.6 out of 10, Exceptional, (163)
"This BNB is delightful. Great location and easy to find in town. Lovely house, room, easy check in, and the owner was great. The owner was there when we checked in and gave us a tour and recommendations for dinner in town. Downtown is just darling and easy walking around the town square. Dinner in town was excellent as well. I would highly recommend a stay here to anyone. "
United States
Tina
$174 nightly
The price is $189
Dec 1 - Dec 2
Total with taxes and fees
The Carriage Barn Inn
Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (338)
"Very charming place. Breakfast was really good, made fresh, very accommodating with food intolerances. Very much enjoyed my stay."
Canada
Carolyn
$150 nightly
The price is $166
Nov 20 - Nov 21
Total with taxes and fees
Colonel Williams Inn
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

3.0 star property
West Dover
9.6 out of 10, Exceptional, (83)
"We had a lovely time staying here. "
United States
Jeff
$94 nightly
The price is $104
Nov 16 - Nov 17
Total with taxes and fees
Deerfield Valley Inn
Exclusive Room | Living area | 20-inch TV with cable channels
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.6 out of 10, Exceptional, (9)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
$125 nightly
The price is $137
Dec 9 - Dec 10
Total with taxes and fees
Four Columns Inn
Free daily full breakfast
Centennial House

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (172)
"The property was wonderful and the hosts exceptional❤️"
United States
Susan
$199 nightly
The price is $210
Nov 10 - Nov 11
Total with taxes and fees
Centennial House
Exterior
Inn on Putney Road

Inn on Putney Road

4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (55)
"Pricey but overall. A wonderful stay. Excellent breakfast, grounds, shower and inn keeper."
United States
Jane
$267 nightly
The price is $294
Nov 9 - Nov 10
Total with taxes and fees
Inn on Putney Road
Exterior
The Engel House

The Engel House

3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (16)
"Warm and inviting atmosphere. Great location. "
United States
Diane
$193 nightly
The price is $211
Nov 9 - Nov 10
Total with taxes and fees
The Engel House
Exterior
Green River Bridge Inn

Green River Bridge Inn

3.0 star property
Guilford
8.8 out of 10, Excellent, (12)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
United States
Melissa
$255 nightly
The price is $278
Dec 7 - Dec 8
Total with taxes and fees
Green River Bridge Inn
Mountain view
Windham Hill Inn

Windham Hill Inn

4.0 star property
West Townshend
8.6 out of 10, Excellent, (37)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
United States
Brandon
$200 nightly
The price is $219
Nov 10 - Nov 11
Total with taxes and fees
Windham Hill Inn
Exterior
The One Cat B&B

The One Cat B&B

2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"We loved our stay! Very welcoming and cozy. The breakfast was delicious. Will definitely come back to stay here again!"
United States
Wiley
$245 nightly
The price is $270
Nov 13 - Nov 14
Total with taxes and fees
The One Cat B&B
Exterior
Deerhill Inn

Deerhill Inn

3.5 star property
West Dover
9.6 out of 10, Exceptional, (223)
"An excellent stay! Warm and accommodating and helpful in every way. Wonderful breakfast too!"
United States
Clarence
$195 nightly
The price is $215
Nov 9 - Nov 10
Total with taxes and fees
Deerhill Inn
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"This is a genuine five star property, an ideal of what a country inn should be. Beautifully designed and decorated, comfortable and welcoming, charming staff. One of the nicest places we’ve ever stayed."
United States
Susan
$301 nightly
The price is $327
Nov 9 - Nov 10
Total with taxes and fees
Chesterfield Inn
Outdoor dining
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
Nov 15 - Nov 16
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

The Covered Bridge Inn

The Covered Bridge Inn

10/10 Excellent
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
Zachery 1-night trip
Posted 5 days ago
The Covered Bridge Inn

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
1,317
Accommodation
28 B&B
Lowest Price
$104
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 $104 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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