Photo by Assya A

Find Hotels by Independent in Chestertown from CA $81

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Find properties with these dates

Top Chestertown Independent Hotels

The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (340)
"Everyone was so friendly including the manager. We had a great experience and I cant wait to go back soon. "
The price is CA $327
CA $398 total
includes taxes & fees
May 12 - May 13
The Inn at Chesapeake Bay Beach Club
Vandiver Inn
3.5 star property
9.4 out of 10, Exceptional, (424)
"The owners do a great job keeping up the very old property. It must be constant maintenance and it is in amazing shape. The rooms are lovely; the grounds are beautiful. The staff are all great!"
The price is CA $231
CA $259 total
includes taxes & fees
May 14 - May 15
Vandiver Inn
Hilltop Motel
2.0 star property
4.8 out of 10, (714)
"The girls are very friendly and always ready to help you I really felt at home here "
The price is CA $81
CA $91 total
includes taxes & fees
May 12 - May 13
Hilltop Motel
Save an average of 15% on thousands of hotels when you're signed in
Driftwood Inn
2.0 star property
5.0 out of 10, (159)
"It was clean and everything worked--more than I could say for many other more expensive rooms I've stayed in. The shower was exceptionally good. Watch out for the hot water: very hot! The TV had Netflix, Hulu, Roku, & Vudu. And they worked. On the downside, the furnishings and carpet were worn, but not terrible. "
The price is CA $87
CA $96 total
includes taxes & fees
May 11 - May 12
Driftwood Inn
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is CA $846
CA $1,946 total
includes taxes & fees
May 14 - May 15
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Relax Inn Smyrna
2.0 star property
8.0 out of 10, Very good, (30)
"The room was small and sparsely furnished but was very clean and the owner is a very attentive and friendly person. "
The price is CA $115
CA $128 total
includes taxes & fees
May 12 - May 13
Relax Inn Smyrna
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (67)
"Quiet and beautiful. The staff was very professional and friendly. I felt like I was home. Looking forward to my next visit!!!"
The price is CA $446
CA $554 total
includes taxes & fees
May 12 - May 13
Kent Island Resort
Caribbean Pool Home <1 mile from Matapeake Beach!
10.0 out of 10, Exceptional, (1)
"The house was exactly as promised! We were very happy with the accommodations!"
The price is CA $372
CA $1,121 total
includes taxes & fees
May 12 - May 13
Caribbean Pool Home <1 mile from Matapeake Beach!
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (32)
"Really wonderful host. The apartment was spacious and immaculate. It worked wonderfully for our family gathering with our midshipman."
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (262)
"I was looking to get away for some much needed peace and relaxation and the Heron’s Neat was perfect. I enjoyed sitting outside and listening to and watching the water. I would come back again, thank you!"
The Heron's Nest at Atlantic Marina
Don't see what you're looking for?
See all available properties in Chestertown
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.

Independent Chestertown Hotel Guide

Some globe-trotters will stay anywhere that offers a cheap deal, but others prefer to book with their favourite chain. Thanks to Expedia.ca’s range of Independent in Chestertown, Maryland, you no longer have to choose between the two. Known for their comfortable rooms and friendly staff, each of the best Independent Chestertown promises a top quality travel experience.

Recent Reviews in Chestertown
Expedia verified reviews