Book Chesterfield Bed & Breakfast

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Our top choices for Chesterfield bed & breakfast

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
"Great breakfast!"
United States
Billie
$147 nightly
The price is $161
May 26 - May 27
Total with taxes and fees
Colonel Williams Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (39 reviews)
"The hot tub was so amazing"
United States
Mark
$126 nightly
The price is $138
May 24 - May 25
Total with taxes and fees
Four Columns Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (172 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
$189 nightly
The price is $205
May 25 - May 26
Total with taxes and fees
The Carriage Barn Inn

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (265 reviews)
"Excellent hosts provided a terrific stay!"
United States
Mark
$162 nightly
The price is $176
May 30 - May 31
Total with taxes and fees
Harvest Barn Inn

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (80 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
$239 nightly
The price is $263
May 25 - May 26
Total with taxes and fees
The One Cat B&B

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
$284 nightly
The price is $312
May 24 - May 25
Total with taxes and fees
Inn on Putney Road

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (118 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
$105 nightly
The price is $116
Jun 14 - Jun 15
Total with taxes and fees
Deerfield Valley Inn

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (41 reviews)
"The room was wonderful. SO spacious and well-appointed, extremely clean. Loved the excellent bedding, the soaking tub, the perfect water pressure in the shower. We did not expect the flat-screen TV, so it was a treat to have. Don't let the lack of restaurant bother you: There are plenty of great choices around, though you have a bit of a drive. For a leisurely romantic weekend, I can't think of a better place. "
United States
Debbie
$198 nightly
The price is $216
Jun 16 - Jun 17
Total with taxes and fees
Windham Hill Inn

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (105 reviews)
"Great stay"
United States
Wayne
$301 nightly
The price is $327
May 25 - May 26
Total with taxes and fees
Chesterfield Inn

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
May 28 - May 29
Total with taxes and fees
Private bedroom in the Green River Bridge Inn. A full breakfast is included.

Deerhill Inn

Deerhill Inn
3.5 star property
West Dover
9.6 out of 10, Exceptional, (228 reviews)
"Such a quaint Bed & Breakfast! The Innkeepers are so friendly and welcoming. Each room is individually decorated making it cozy and inviting with fireplaces in each room! So many details! Wonderful homemade breakfast included! Will definitely be back!!!"
United States
carlene
$194 nightly
The price is $213
May 28 - May 29
Total with taxes and fees
Deerhill 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

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
1,196
Accommodation
29 B&B
Lowest Price
$116
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 $116 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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