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Check prices for these dates

Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

B&B in Chesterfield

Our top choices for Chesterfield bed & breakfast

Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (315)
"I enjoyed my stay and found the room more than adequately furnished. Wished the bed could be firmer and they could supply meals other than just breakfast."
$131 nightly
The price is $145
Sep 9 - Sep 10
Total with taxes and fees
Colonel Williams 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 $222
Aug 28 - Aug 29
Total with taxes and fees
Green River Bridge Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (225)
"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."
$130 nightly
The price is $142
Sep 2 - Sep 3
Total with taxes and fees
Harvest Barn Inn
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (161)
"Great breakfast, friendly staff"
$224 nightly
The price is $237
Sep 15 - Sep 16
Total with taxes and fees
Centennial House
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (61)
"Oguz, the manager treated us like family. It was a very pleasant and relaxing stay."
$111 nightly
The price is $123
Aug 28 - Aug 29
Total with taxes and fees
Deerfield Valley Inn
Four Columns Inn
Romantic Room | 1 bedroom, free WiFi, bed sheets

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
$195 nightly
The price is $213
Aug 26 - Aug 27
Total with taxes and fees
Four Columns Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (154)
"Excellent phenomenal cleanliness and so polite"
$191 nightly
The price is $208
Sep 18 - Sep 19
Total with taxes and fees
The Carriage Barn Inn
Windham Hill Inn
Mountain view

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
Aug 27 - Aug 28
Total with taxes and fees
Windham Hill Inn
The Engel House
Exterior

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 26 - Aug 27
Total with taxes and fees
The Engel House
The One Cat B&B
Exterior

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!"
$203 nightly
The price is $223
Aug 27 - Aug 28
Total with taxes and fees
The One Cat B&B
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (51)
"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 26 - Aug 27
Total with taxes and fees
Inn on Putney Road
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
$301 nightly
The price is $327
Aug 27 - Aug 28
Total with taxes and fees
Chesterfield Inn
Deerhill Inn
Exterior

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
Sep 7 - Sep 8
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

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

10/10 Excellent
"Great experience but our only issue was that the sink was outside of the bathroom in the sleeping area other than that I would definitely recommend this hotel and stay again. The hotel was spotless and the breakfast was very good for what we paid for the room, 9 out of 10 just because of the wash hand basin location. "
Sharon 1-night trip
Posted 2 days ago
Keene Elm City Hotel, Ascend Hotel Collection

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.