Book Chesterfield Bed & Breakfast

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Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3
In one month
Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Compare 27 B&B in Chesterfield with updated reviews, rates, and availability.

Centennial House
Enjoy meals in a beautifully lit dining area with arched windows and a view of the outdoors.

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (155)
"This historic property is very nice. Beds are comfortable. The hosts are very welcoming and communication was very good. Breakfast was outstanding! I highly recommend this property and hope to return for another visit someday. "
$193 nightly
The price is $204
Jul 16 - Jul 17
Total includes taxes and fees
Centennial House
The Carriage Barn Inn
Enjoy a meal with a view from this dining table near a window.

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (152)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
$200 nightly
The price is $218
Aug 14 - Aug 15
Total includes taxes and fees
The Carriage Barn Inn
Harvest Barn Inn
Enjoy a serene lake view from the balcony, where two Adirondack chairs await.

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (221)
"Very accommodating and wonderful people! Hoping to return!"
$170 nightly
The price is $186
Jul 30 - Jul 31
Total includes taxes and fees
Harvest Barn Inn
Green River Bridge Inn
Exterior

Green River Bridge Inn

3.0 star property
10.0 out of 10, Exceptional, (2)
"Such a peaceful, beautiful area and inn! The host is wonderful and an amazing cook. The quintessential Vermont inn with an international flair. Can’t wait to go back!"
$203 nightly
The price is $221
Jul 15 - Jul 16
Total includes taxes and fees
Green River Bridge Inn
Inn on Putney Road
Classic two-story house with a gabled roof and symmetrical facade, surrounded by a well-maintained garden and a white fence.

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (48)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
$265 nightly
The price is $292
Jul 15 - Jul 16
Total includes taxes and fees
Inn on Putney Road
Colonel Williams Inn
Stunning hotel set amidst a serene autumn landscape.

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (307)
"The inn keepers are always super friendly and the place is kept well. The breakfast is delicious. Great for families who prefer quiet and quaint."
$142 nightly
The price is $155
Jul 23 - Jul 24
Total includes taxes and fees
Colonel Williams Inn
Deerfield Valley Inn
Surrounded by snow-covered trees, this serene winter scene offers a peaceful retreat.

Deerfield Valley Inn

3.0 star property
9.4 out of 10, Exceptional, (51)
"Overall great spot!"
$112 nightly
The price is $124
Jul 24 - Jul 25
Total includes taxes and fees
Deerfield Valley Inn
Windham Hill Inn
Guests can enjoy a serene view of the surrounding landscape from this outdoor deck.

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. "
$202 nightly
The price is $221
Jul 15 - Jul 16
Total includes taxes and fees
Windham Hill Inn
Chesterfield Inn
Cozy living room with a rustic fireplace, large windows, and classic furnishings.

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (103)
"Great stay"
$301 nightly
The price is $327
Jul 15 - Jul 16
Total includes taxes and fees
Chesterfield Inn
The One Cat B&B
Stroll through the serene garden, surrounded by vibrant blooms and a whimsical cat-themed sign.

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
$214 nightly
The price is $236
Jul 20 - Jul 21
Total includes taxes and fees
The One Cat B&B
The Engel House
Guests can enjoy a warm welcome on the porch with outdoor seating.

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
Jul 15 - Jul 16
Total includes taxes and fees
The Engel House
Four Columns Inn
Relax in this stylish room with two armchairs, a coffee table, and a large window overlooking a charming view.

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Outdoor dining

Private bedroom in the Green River Bridge Inn. A full breakfast is included.

$252 nightly
The price is $282
Jul 21 - Jul 22
Total includes taxes and fees
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Deerhill Inn
Stunning two-story house with a front porch and stone wall, set amidst a lush lawn.

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"Never disappoints!"
$187 nightly
The price is $206
Jul 20 - Jul 21
Total includes taxes and fees
Deerhill Inn
The Brattleboro
Hiking

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
Deluxe Room with Fireplace Room 2
Relax in a warm and inviting space with a large bed, comfortable armchair, and cozy fireplace.

Deluxe Room with Fireplace Room 2

Deluxe Room with Fireplace Room 2
Deerfield Valley Inn - Deluxe Room with Fireplace Room 4
Classic bedroom with a large bed, bedside tables, and a ceiling fan.

Deerfield Valley Inn - Deluxe Room with Fireplace Room 4

Deerfield Valley Inn - Deluxe Room with Fireplace Room 4
Deerfield Valley Inn, 5min. to M.Snow Room Entire Inn
Enjoy cooking in this well-equipped kitchen with a stove, microwave, and dishwasher.

Deerfield Valley Inn, 5min. to M.Snow Room Entire Inn

Deerfield Valley Inn, 5min. to M.Snow Room Entire Inn
Deerfield Valley Inn - Deluxe Room with Fireplace Room 5
Relax in a spacious room with a large bed, nightstand, and comfortable seating area.

Deerfield Valley Inn - Deluxe Room with Fireplace Room 5

Deerfield Valley Inn - Deluxe Room with Fireplace Room 5
Deerfield Valley Inn - Standard Room 7
Classic hotel room with a neatly made bed, armchair, and bedside table.

Deerfield Valley Inn - Standard Room 7

Deerfield Valley Inn - Standard Room 7
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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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 $124 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.