Photo by Assya A

Search Kent County Hotels

    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

Top Cities in Kent County

HotelsHotels

Chestertown

Chestertown

Check prices for these dates

Tonight
Aug 7 - Aug 8
Tomorrow
Aug 8 - Aug 9
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Filter by

Guest rating
Guest rating
Star rating

Top Hotels in Kent County

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (791)
"It was a clean comfortable spot to rest for the night. "
The price is CA $151
CA $167 total
includes taxes & fees
Aug 17 - Aug 18
Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (58)
"Great place to get some quiet rest by the water"
The price is CA $182
CA $202 total
includes taxes & fees
Aug 12 - Aug 13
The Lodge at Great Oak Landing
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (384)
"Good location."
The price is CA $99
CA $110 total
includes taxes & fees
Aug 14 - Aug 15
Red Roof Inn & Suites Chestertown
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 $234
CA $260 total
includes taxes & fees
Aug 13 - Aug 14
Inn at Huntingfield Creek
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
10.0 out of 10, Exceptional, (1)
"We recently had the pleasure of staying at the Inn at Haven Harbour, specifically at their south location, and can't say enough good things about our experience! From the moment we arrived, we were captivated by the immaculate property and stunning surroundings. The views of the water were breathtaking, and having access to a private beach made our stay feel even more special. The amenities were top-notch, with a pool available for those who prefer a swim to the beach. The staff were incredibly...
The price is CA $288
CA $347 total
includes taxes & fees
Aug 12 - Aug 13
Inn at Haven Harbour
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is CA $87
CA $97 total
includes taxes & fees
Aug 11 - Aug 12
Driftwood Inn
Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is CA $213
CA $237 total
includes taxes & fees
Aug 10 - Aug 11
Mariners Motel
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

10.0 out of 10, Exceptional, (16)
"The staff was great"
The price is CA $84
CA $162 total
includes taxes & fees
Aug 12 - Aug 13
Guest Suite for up to 2 in a Victorian on the Chester River
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (10)
"Perfection"
The price is CA $170
CA $402 total
includes taxes & fees
Aug 12 - Aug 13
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (93)
"Very pretty location. Few minutes drive to town center."
The price is CA $136
CA $218 total
includes taxes & fees
Aug 13 - Aug 14
First Floor Studio Apartment in Historic Chestertown
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (43)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is CA $275
CA $411 total
includes taxes & fees
Aug 11 - Aug 12
BAYSIDE BUNGALOW
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (22)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
The price is CA $309
CA $517 total
includes taxes & fees
Aug 11 - Aug 12
Waterfront Retreat with Private Dock and Beach
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio

Grandma’s Cottage will wrap around you like a warm hug

The price is CA $309
CA $575 total
includes taxes & fees
Aug 13 - Aug 14
Grandma’s Cottage will wrap around you like a warm hug
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

9.0 out of 10, Wonderful, (4)
"This property is near many of the downtown places you want to visit, and all are within walking distance. "
Knot's Landing, spacious Apt. downtown Rock Hall
Cute waterfront apartment -- 8 min from the beach!
Outdoor dining

Cute waterfront apartment -- 8 min from the beach!

10.0 out of 10, Exceptional, (6)
"Nice and quiet with a great location and amazing view!!!"
Cute waterfront apartment -- 8 min from the beach!
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Beach towels

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

9.8 out of 10, Exceptional, (61)
"It’s a nice place"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (115)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Outdoor pool

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Charming cottage with Pool Access and WiFi in lovely Rock Hall
River Cottage, Chestertown
Fridge, microwave, oven, stovetop

River Cottage, Chestertown

2.0 star property
8.0 out of 10, Very good, (1)
"Location is very quiet and tranquil. "
River Cottage, Chestertown
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (36)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
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 Kent County Hotel Reviews

The Royal Sonesta Harbor Court Baltimore

The Royal Sonesta Harbor Court Baltimore

10/10 Excellent
"I was able to check in 2 hours early and it was quick and easy. The staff member who checked me in was extremely friendly and had provided great customer service. "
Stephanie 1-night trip
Posted 21 hours ago
The Royal Sonesta Harbor Court Baltimore