Book Chesterfield Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out
    bundle and save illustration

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
    one key illustration

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

B&B in Chesterfield

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (320)
"We stayed one night. We were able to get checked early, enjoyed breakfast, quiet and charming atmosphere. Owners are very friendly. "
$150 nightly
The price is $166
Oct 2 - Oct 3
Total with taxes and fees
Colonel Williams Inn

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (67)
"We had a lovely time staying here. "
$105 nightly
The price is $116
Sep 28 - Sep 29
Total with taxes and fees
Deerfield Valley Inn

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (233)
"Breakfast was amazing! Hosts were super friendly and we are looking forward to returning there again! "
$166 nightly
The price is $181
Oct 13 - Oct 14
Total with taxes and fees
Harvest Barn Inn

Green River Bridge Inn

3.0 star property
8.6 out of 10, Excellent, (8)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
$235 nightly
The price is $257
Oct 7 - Oct 8
Total with taxes and fees
Green River Bridge Inn

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (156)
"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 29 - Sep 30
Total with taxes and fees
The Carriage Barn Inn

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (164)
"The property was wonderful and the hosts exceptional❤️"
$224 nightly
The price is $237
Oct 27 - Oct 28
Total with taxes and fees
Centennial House

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
$173 nightly
The price is $189
Oct 6 - Oct 7
Total with taxes and fees
Four Columns 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. "
$202 nightly
The price is $221
Oct 21 - Oct 22
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!"
$193 nightly
The price is $213
Oct 26 - Oct 27
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 28 - Sep 29
Total with taxes and fees
Inn on Putney Road

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (77)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
$288 nightly
The price is $317
Sep 29 - Sep 30
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 28 - Sep 29
Total with taxes and fees
The Engel House

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
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 - Budget Club Room 3

Deerfield Valley Inn - Budget Club Room 3

Deerfield Valley Inn - Standard Room 6

Deerfield Valley Inn - Standard Room 6

Deerfield Valley Inn - Deluxe Room with Fireplace Room 4

Deerfield Valley Inn - Deluxe Room with Fireplace Room 4

Deerfield Valley Inn - Suite Room

Deerfield Valley Inn - Suite Room

Deerfield Valley Inn - Standard Room 7

Deerfield Valley Inn - Standard Room 7

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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesterfield Hotel Reviews

Find out more about Chesterfield

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
1,237
Accommodation
28 B&B
Lowest Price
$116
Highest Price
$399

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 $116 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia