Photo by Assya A

Find a Bed and Breakfast in Chestertown from CA $135

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Chestertown B&B

Inn at Haven Harbour
View from property

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 $290
CA $353 total
includes taxes & fees
Aug 24 - Aug 25
Inn at Haven Harbour
Vandiver Inn
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio

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 $207
CA $232 total
includes taxes & fees
Aug 21 - Aug 22
Vandiver Inn
Inn at Huntingfield Creek
Lake

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 $222
CA $247 total
includes taxes & fees
Aug 24 - Aug 25
Inn at Huntingfield Creek
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (76)
"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 $242
CA $276 total
includes taxes & fees
Aug 24 - Aug 25
Flag House Inn
Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy
Interior

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 $135
CA $560 total
includes taxes & fees
Aug 22 - Aug 23
Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy
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
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Stayed for a baseball tournament and was pleased with everything from check in, to check out. Clean, spacious and everything in working order. Would stay again. "
Patrick 2-night trip
Posted 1 day ago
Hampton Inn & Suites Edgewood/Aberdeen-South