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
Apr 17 - Apr 19
In two weeks
Apr 24 - Apr 26
In one month
May 8 - May 10
In two months
Jun 5 - Jun 7

Our top choices for Chesterfield bed & breakfast

Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (171 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
$142 nightly
The price is $154
Apr 12 - Apr 13
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, (257 reviews)
"Staff were wonderful, food was excellent, environment was peaceful, everything was clean and in decent condition."
United States
Charles
$129 nightly
The price is $141
Apr 14 - Apr 15
Total with taxes and fees
Harvest Barn Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful location and nice staff."
United States
Cynthia
$120 nightly
The price is $131
May 11 - May 12
Total with taxes and fees
Four Columns Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (350 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
$156 nightly
The price is $172
May 12 - May 13
Total with taxes and fees
Colonel Williams Inn
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (79 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
$233 nightly
The price is $256
Apr 20 - Apr 21
Total with taxes and fees
The One Cat B&B
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (115 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
$98 nightly
The price is $108
May 12 - May 13
Total with taxes and fees
Deerfield Valley Inn
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
$250 nightly
The price is $275
Apr 12 - Apr 13
Total with taxes and fees
Inn on Putney Road
Free daily full breakfast

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (174 reviews)
"great proprietors beautiful vintage home excellent breakfast"
United States
JAMES
$169 nightly
The price is $179
May 3 - May 4
Total with taxes and fees
Centennial House
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very Good, (40 reviews)
"We had a fantastic room! Staff was very friendly and accommodating. Though we visited during peak foliage season, we’ll be trying to book again in the near future to try out the pool."
United States
J
$179 nightly
The price is $195
May 11 - May 12
Total with taxes and fees
Windham Hill Inn
Front of property - evening/night

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
Apr 19 - Apr 20
Total with taxes and fees
Chesterfield Inn
Exterior

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
Deerhill 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
$311 nightly
The price is $348
Apr 18 - Apr 19
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

Colonial Motel And Spa

Colonial Motel And Spa

2/10 Terrible
"Eletric was out without. Found a note on door at check.in to call and they said no information if reopening. Man was pleasant not his fault he is employee. had to find another place that night. Expedia helped. "
Grace 1-night trip
Posted 1 day ago
Colonial Motel And Spa

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
1,148
Accommodation
29 B&B
Lowest Price
$108
Highest Price
$348

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 $108 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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