Photo by Assya A

Book 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
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sept - 7 Sept

Filter by

Guest rating
Guest rating
Property class

Top Hotels in Kent County

Our top choices for Kent County hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (804)
"Friendly staff, clean room, convenient location. "
The price is AU$188
includes taxes & fees
7 Sept - 8 Sept
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, (66)
"Great place to get some quiet rest by the water"
The price is AU$226
includes taxes & fees
7 Sept - 8 Sept
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, (388)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is AU$131
includes taxes & fees
2 Sept - 3 Sept
Red Roof Inn & Suites Chestertown
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 AU$349
includes taxes & fees
17 Sept - 18 Sept
Inn at Haven Harbour
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (53)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (174)
"Rooms are clean, staf was helpful "
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 AU$265
includes taxes & fees
1 Sept - 2 Sept
Mariners Motel
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, (12)
"A very well maintained and comfy apartment that is just a short walk to the heart of Rock Hall. My family especially enjoyed the large private backyard. Rick made sure we had everything we needed."
The price is AU$447
includes taxes & fees
28 Aug - 29 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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 AU$185
includes taxes & fees
4 Sept - 5 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (99)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is AU$233
includes taxes & fees
28 Aug - 29 Aug
First Floor Studio Apartment in Historic Chestertown
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (46)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is AU$469
includes taxes & fees
28 Aug - 29 Aug
BAYSIDE BUNGALOW
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
The price is AU$586
includes taxes & fees
9 Sept - 10 Sept
Waterfront Retreat with Private Dock and Beach
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

9.2 out of 10, Wonderful, (5)
"Spent the weekend here. Great location close to everything. Bikes were provided and you can ride to anything in Rock Hall. We would definitely rent here again."
Knot's Landing, spacious Apt. downtown Rock Hall
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 AU$640
includes taxes & fees
2 Sept - 3 Sept
Grandma’s Cottage will wrap around you like a warm hug
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, (63)
"It’s a nice place"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.
Fridge, microwave, oven, stovetop

Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

2.0 star property
8.8 out of 10, Excellent, (3)
"Would I stay here again? No. Would I recommend it to a friend? Also no.While the unit was clean, it felt quite tired and in need of a refresh. The kitchen was minimally equipped, with very few pots and pans, making it difficult to cook meals. Additionally, there were air fresheners and purifiers in every room, which made us wonder if they were masking an underlying issue. Overall, the space could benefit from some updates and better preparation for guests."
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.
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, (116)
"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

10.0 out of 10, Exceptional, (2)
"Adorable little cottage and amenities. Owners very nice. Perfect little getaway. "
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Cute waterfront apartment -- 8 min from the beach!
Outdoor dining

Cute waterfront apartment -- 8 min from the beach!

9.6 out of 10, Exceptional, (7)
"Nice and quiet with a great location and amazing view!!!"
Cute waterfront apartment -- 8 min from the beach!
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Exterior detail

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

10.0 out of 10, Exceptional, (11)
"We really enjoyed our long weekend at The Oyster Cottage. We needed some rest and relaxation and this cottage was perfect. Very well maintained and stocked! "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Friendly and accommodating staff! Room was bright, comfortable, cozy, and clean! Nice amenities like a small fridge and single cup coffee maker in the room. Be careful stepping into the shower, as it's a little slippery. Perhaps some "non-skid" strips or a mat of some sort on the bottom of the tub. Overall, great stay! Highly recommend! "
AnnMarie 4-night trip
Posted 1 day ago
Historic Inns of Annapolis

Explore a world of travel with Expedia

Explore a world of travel with Expedia