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

Book Chesterfield Bed & Breakfast

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Chesterfield bed & breakfast

Exterior

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
$295 nightly
The price is $324
Sep 8 - Sep 9
Total with taxes and fees
Inn on Putney Road
Land view from property

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
$128 nightly
The price is $140
Sep 7 - Sep 8
Total with taxes and fees
Four Columns Inn
Front of property

3. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (358 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
$139 nightly
The price is $152
Oct 6 - Oct 7
Total with taxes and fees
Colonel Williams Inn
Property entrance

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
$270 nightly
The price is $297
Oct 6 - Oct 7
Total with taxes and fees
The One Cat B&B
Breakfast area

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
$175 nightly
The price is $190
Sep 8 - Sep 9
Total with taxes and fees
The Carriage Barn Inn
Front of property

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
$191 nightly
The price is $202
Sep 14 - Sep 15
Total with taxes and fees
Centennial House
Porch

7. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (278 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
$164 nightly
The price is $179
Sep 9 - Sep 10
Total with taxes and fees
Harvest Barn Inn
Exterior

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
$118 nightly
The price is $130
Sep 14 - Sep 15
Total with taxes and fees
Deerfield Valley Inn
Outdoor dining

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
$314 nightly
The price is $352
Sep 13 - Sep 14
Total with taxes and fees
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Room, 1 Queen Bed, Garden View | Mountain view

10. Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (44 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
$259 nightly
The price is $282
Sep 22 - Sep 23
Total with taxes and fees
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"All around great stay. Thank you."
Christina 3-night trip
Posted 15 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
1,256
Accommodation
14 B&B
Lowest Price
$130
Highest Price
$352

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 $130 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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