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B&B in Chesterfield

Our top choices for Chesterfield bed & breakfast

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"We had a lovely time staying here. "
$106 nightly
The price is $117
Sep 18 - Sep 19
Total with taxes and fees
Deerfield Valley Inn

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (318)
"We stayed one night. We were able to get checked early, enjoyed breakfast, quiet and charming atmosphere. Owners are very friendly. "
$156 nightly
The price is $172
Sep 21 - Sep 22
Total with taxes and fees
Colonel Williams Inn

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (228)
"Lovely setting and excellent breakfast. Very friendly owners ."
$168 nightly
The price is $184
Sep 20 - Sep 21
Total with taxes and fees
Harvest Barn Inn

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (163)
"Great breakfast, friendly staff"
$224 nightly
The price is $237
Sep 21 - Sep 22
Total with taxes and fees
Centennial House

Green River Bridge Inn

3.0 star property
8.4 out of 10, Very Good, (7)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
$234 nightly
The price is $256
Oct 16 - Oct 17
Total with taxes and fees
Green River Bridge Inn

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (155)
"Very quiet and peaceful but at the same time it's right down the street from Main Street. Joe the owner was so nice! "
$197 nightly
The price is $214
Sep 18 - Sep 19
Total with taxes and fees
The Carriage Barn Inn

Windham Hill Inn

4.0 star property
8.4 out of 10, Very Good, (36)
"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. "
$208 nightly
The price is $227
Sep 18 - Sep 19
Total with taxes and fees
Windham Hill Inn

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (221)
"An excellent stay! Warm and accommodating and helpful in every way. Wonderful breakfast too!"
$203 nightly
The price is $224
Sep 18 - Sep 19
Total with taxes and fees
Deerhill Inn

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (54)
"Outstanding breakfast in a charming home. A 15 minute walk excellent to restaurants and art galleries."
$363 nightly
The price is $399
Sep 18 - Sep 19
Total with taxes and fees
Inn on Putney Road

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (76)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
$294 nightly
The price is $324
Oct 16 - Oct 17
Total with taxes and fees
The One Cat B&B

The Engel House

3.0 star property
9.4 out of 10, Exceptional, (13)
"The perfect Vermont Bed and Breakfast. "
$193 nightly
The price is $211
Sep 18 - Sep 19
Total with taxes and fees
The Engel House

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
$221 nightly
The price is $241
Oct 15 - Oct 16
Total with taxes and fees
Four Columns Inn

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
$427 nightly
The price is $463
Sep 18 - Sep 19
Total with taxes and fees
Chesterfield Inn

The Brattleboro

4.0 star property
10.0 out of 10, Exceptional, (5)
"Peaceful, comfortable, great views. We were made welcome and had wonderful beverage and snack options and the Breakfast were Superior. We will definitely return. "
The Brattleboro

Deerfield Valley Inn - Deluxe Room with Fireplace Room 4

Deerfield Valley Inn - Deluxe Room with Fireplace Room 4

Deerfield Valley Inn - Standard Room 7

Deerfield Valley Inn - Standard Room 7

Deerfield Valley Inn - Suite Room

Deerfield Valley Inn - Suite Room

Deerfield Valley Inn - Deluxe Room with Fireplace Room 8

Deerfield Valley Inn - Deluxe Room with Fireplace Room 8

Deluxe Room with Fireplace Room 2

Deluxe Room with Fireplace Room 2

Deluxe Room with Fireplace Room 1

Deluxe Room with Fireplace Room 1
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

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
1,227
Accommodation
28 B&B
Lowest Price
$117
Highest Price
$463

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 $117 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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