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
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

Our top choices for Chesterfield bed & breakfast

Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (357 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
$158 nightly
The price is $173
Jul 20 - Jul 21
Total with taxes and fees
Colonel Williams Inn
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
$181 nightly
The price is $196
Jul 22 - Jul 23
Total with taxes and fees
The Carriage Barn Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (268 reviews)
"Amazing property and hosts...If you are looking for a quiet getaway with a river view and gourmet breakfast, look no further!"
United States
Paul
$164 nightly
The price is $179
Jul 20 - Jul 21
Total with taxes and fees
Harvest Barn Inn
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (58 reviews)
"Fabulous home, breakfast, staff, and location. Excellent value! Will definitely be back!"
United States
Mary
$295 nightly
The price is $324
Jul 19 - Jul 20
Total with taxes and fees
Inn on Putney Road
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (125 reviews)
"Very friendly and courteous owner, great location 5 mins away from Mount Snow."
United States
Brandon
$124 nightly
The price is $136
Aug 2 - Aug 3
Total with taxes and fees
Deerfield Valley Inn
Front of property

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
$232 nightly
The price is $255
Jul 26 - Jul 27
Total with taxes and fees
The One Cat B&B
Front of property - evening/night

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
Jul 19 - Jul 20
Total with taxes and fees
Chesterfield Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (47 reviews)
"Can’t go wrong with this place."
United States
John
$213 nightly
The price is $232
Aug 11 - Aug 12
Total with taxes and fees
Four Columns 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
Jul 24 - Jul 25
Total with taxes and fees
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Exterior

Deerhill Inn

Deerhill Inn
3.5 star property
West Dover
9.6 out of 10, Exceptional, (228 reviews)
"Amazing staff and place to stay. Wish it was for more than one night! "
United States
Gregory
$194 nightly
The price is $213
Jul 26 - Jul 27
Total with taxes and fees
Deerhill Inn
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (43 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
$207 nightly
The price is $225
Jul 29 - Jul 30
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Clean, comfortable and fairly priced."
Cynthia 1-night trip
Posted 20 hours ago
Hampton Inn Brattleboro

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
1,487
Accommodation
13 B&B
Lowest Price
$136
Highest Price
$327

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 $136 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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