Photo by Assya A

Find a Bed and Breakfast in Chestertown from CA $192

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Chestertown B&B

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (507)
"Staff was very friendly. We had a very relaxing stay. "
The price is CA $197
CA $221 total
includes taxes & fees
Aug 18 - Aug 19
Vandiver Inn

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
The price is CA $288
CA $347 total
includes taxes & fees
Aug 12 - Aug 13
Inn at Haven Harbour

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (73)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is CA $192
CA $219 total
includes taxes & fees
Aug 12 - Aug 13
Flag House Inn

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
The price is CA $234
CA $260 total
includes taxes & fees
Aug 13 - Aug 14
Inn at Huntingfield Creek

Naomi Bed & Breakfast

3.0 star property
8.6 out of 10, Excellent, (15)
"Friendly and super clean."
Naomi Bed & Breakfast

Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy

10.0 out of 10, Exceptional, (1)
"Overall great place. Nice neighborhood. Very spacious and clean living area. Loved having the pool table and all the games. Lisa is a great host and the breakfast is delicious. "
The price is CA $207
CA $645 total
includes taxes & fees
Aug 16 - Aug 17
Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy

Private room for one person 18+ years only. Text for availability 973-477-4574

Private room for one person 18+ years only. Text for availability 973-477-4574

Surf Condominiums - Downtown Bethany

Surf Condominiums - Downtown Bethany
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 Chestertown Hotel Reviews