Book Chesterfield Bed & Breakfast

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Aug 15 - Aug 17
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Oct 3 - Oct 5

B&B in Chesterfield

Colonel Williams Inn
Stunning hotel set amidst a serene autumn landscape.

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (310)
"Excellent. Wonderful breakfast. "
$143 nightly
The price is $156
Aug 18 - Aug 19
Total includes taxes and fees
Colonel Williams Inn
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, (159)
"Lovely property and innkeepers, I was in the area for an event and hope to come back. "
$201 nightly
The price is $213
Aug 10 - Aug 11
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, (153)
"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."
$177 nightly
The price is $193
Sep 2 - Sep 3
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, (223)
"A refurbished old Vermont home with a beautiful view of the Connecticut river. The young couple who own the home were delightful and very attentive. It was comfortable and very unique. I would certainly stay here again."
$141 nightly
The price is $154
Aug 19 - Aug 20
Total includes taxes and fees
Harvest Barn Inn
Green River Bridge Inn
Exterior

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. "
$203 nightly
The price is $221
Aug 6 - Aug 7
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, (49)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
$295 nightly
The price is $324
Aug 6 - Aug 7
Total includes taxes and fees
Inn on Putney Road
Deerfield Valley Inn
Surrounded by snow-covered trees, this serene winter scene offers a peaceful retreat.

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (54)
"I liked that it was right on the scenic route"
$111 nightly
The price is $123
Aug 19 - Aug 20
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. "
$201 nightly
The price is $220
Aug 10 - Aug 11
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, (104)
"Great stay"
$301 nightly
The price is $327
Aug 6 - Aug 7
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!"
$196 nightly
The price is $216
Aug 27 - Aug 28
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
Aug 10 - Aug 11
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
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)
"The innkeepers were such nice, friendly, helpful people, going out of their way to see that we had a delicious breakfast before our early departure. We loved everything about this inn! "
$187 nightly
The price is $206
Aug 10 - Aug 11
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
Deerfield Valley Inn - Suite Room
Cozy living room with a fireplace, sofa, and armchair, perfect for relaxing after a day outdoors.

Deerfield Valley Inn - Suite Room

Deerfield Valley Inn - Suite Room
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
Deluxe Room with Fireplace Room 1
Enjoy a comfortable stay in this well-appointed space with a large bed, ceiling fan, and fireplace.

Deluxe Room with Fireplace Room 1

Deluxe Room with Fireplace Room 1
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 - Budget Club Room 3
Cozy bedroom with a sloped ceiling, featuring a central bed with a patterned bedspread and bedside table.

Deerfield Valley Inn - Budget Club Room 3

Deerfield Valley Inn - Budget Club Room 3
Deerfield Valley Inn - Deluxe Room with Fireplace Room 8
Classic bedroom with a large bed, nightstands, and a sofa, set against a dark floral wallpaper backdrop.

Deerfield Valley Inn - Deluxe Room with Fireplace Room 8

Deerfield Valley Inn - Deluxe Room with Fireplace Room 8
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

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent
"Heated pool and view of the bay were great"
Julie 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG

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 $123 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.