Find a Bed and Breakfast in Chesterfield from CA $160

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jun 12 - Jun 14
In two weeks
Jun 19 - Jun 21
In one month
Jul 3 - Jul 5
In two months
Jul 31 - Aug 2

Our top choices for Chesterfield bed & breakfast

Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (172 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is CA $234
CA $254 total
includes taxes & fees
Jun 16 - Jun 17
The Carriage Barn Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (39 reviews)
"The hot tub was so amazing"
United States
Mark
The price is CA $172
CA $187 total
includes taxes & fees
Jun 15 - Jun 16
Four Columns Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (266 reviews)
"Excellent hosts provided a terrific stay!"
United States
Mark
The price is CA $221
CA $241 total
includes taxes & fees
Jun 22 - Jun 23
Harvest Barn Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
"Great breakfast!"
United States
Billie
The price is CA $211
CA $233 total
includes taxes & fees
Jun 4 - Jun 5
Colonel Williams Inn
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (80 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is CA $346
CA $381 total
includes taxes & fees
Jun 5 - Jun 6
The One Cat B&B
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (120 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
The price is CA $111
CA $160 total
includes taxes & fees
Jun 14 - Jun 15
Deerfield Valley Inn
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (58 reviews)
"Fabulous home, breakfast, staff, and location. Excellent value! Will definitely be back!"
United States
Mary
The price is CA $393
CA $432 total
includes taxes & fees
Jun 8 - Jun 9
Inn on Putney Road
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (41 reviews)
"The room was wonderful. SO spacious and well-appointed, extremely clean. Loved the excellent bedding, the soaking tub, the perfect water pressure in the shower. We did not expect the flat-screen TV, so it was a treat to have. Don't let the lack of restaurant bother you: There are plenty of great choices around, though you have a bit of a drive. For a leisurely romantic weekend, I can't think of a better place. "
United States
Debbie
The price is CA $257
CA $280 total
includes taxes & fees
Jun 15 - Jun 16
Windham Hill Inn
Front of property - evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (105 reviews)
"Great stay"
United States
Wayne
The price is CA $417
CA $452 total
includes taxes & fees
Jun 4 - Jun 5
Chesterfield Inn
Outdoor dining

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

Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Guilford
The price is CA $381
CA $485 total
includes taxes & fees
Jun 9 - Jun 10
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Exterior

Deerhill Inn

Deerhill Inn
3.5 star property
West Dover
9.6 out of 10, Exceptional, (228 reviews)
"Amazing staff and place to stay. Wish it was for more than one night! "
United States
Gregory
The price is CA $274
CA $301 total
includes taxes & fees
Jun 15 - Jun 16
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

The Putney Inn

The Putney Inn

4/10 Poor
"Room smelled disgustingly moldy"
Cooper 2-night trip
Posted 2 days ago
The Putney Inn

Find out more about Chesterfield

Chesterfield B&B information

Number of reviews
1,317
Accommodation
29 B&B
Lowest Price
CA $160
Highest Price
CA $485

Frequently asked questions

What is the nightly rate for a B&B in Chesterfield?
Prices for B&Bs in Chesterfield often vary, but you can find a great deal from CA $160 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.
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