Search Hotels in Kent County

Start date: Check-in selected.
To Date
End date: Check-out

Top Cities in Kent County

Somewhere over the rainbow... Terrific view on the plane back to the North.
HotelsHotels

Chestertown

Chestertown

Check prices for these dates

Tonight
Dec 7 - Dec 8
Tomorrow
Dec 8 - Dec 9
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Filter by

Guest rating
Guest rating
Star rating

Compare 2,363 hotels in Kent County with room rates, reviews, and availability. Most hotels are fully refundable.

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (858)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
$102 nightly
The price is $113
Dec 25 - Dec 26
Total with taxes and fees
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (420)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
$72 nightly
The price is $80
Dec 14 - Dec 15
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
8.0 out of 10, Very Good, (76)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Dec 8 - Dec 9
Total with taxes and fees
The Lodge at Great Oak Landing
Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (57)
"We stayed one night for our Anniversary, and the stay was so peaceful. The grounds are beautiful, the staff so nice, and the main house is amazing. We definitely plan on making this an annual thing!"
United States
Aaron
$144 nightly
The price is $160
Dec 9 - Dec 10
Total with taxes and fees
Inn at Huntingfield Creek
View from property
Inn at Haven Harbour

Inn at Haven Harbour

3.0 star property
Rock Hall
8.6 out of 10, Excellent, (4)
"Friendly staff at check in. This lady was helpful thru entire stay. Her name is Sharon. The Harbor had a Luau on Saturday which we attended since our son is a slip holder. Great weekend. "
United States
Gloria
Inn at Haven Harbour
Marina
Mariners Motel

Mariners Motel

2.0 star property
Rock Hall
9.4 out of 10, Exceptional, (90)
"Although I booked this thinking it was a different place, lol it was a VERY nice and clean, peaceful, convenient retreat. It was actually a better choice than my original selection, You can walk to most things in town and the cleanliness, and charm and quiet were just what I needed to relax. "
United States
Michael
Mariners Motel
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 8 - Dec 9
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Front of property - evening/night
Driftwood Inn

Driftwood Inn

2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
$64 nightly
The price is $70
Dec 24 - Dec 25
Total with taxes and fees
Driftwood Inn
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

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

Millington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
$118 nightly
The price is $125
Dec 8 - Dec 9
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Outdoor dining
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$262 nightly
The price is $278
Jan 1 - Jan 2, 2026
Total with taxes and fees
BAYSIDE BUNGALOW
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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

Rock Hall
10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
$264 nightly
The price is $292
Dec 9 - Dec 10
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach
Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach

Worton
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
$282 nightly
The price is $311
Dec 8 - Dec 9
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
$257 nightly
The price is $272
Dec 8 - Dec 9
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants
Terrace/patio
High Tide Haven Suite

High Tide Haven Suite

Kent County
$195 nightly
The price is $202
Dec 8 - Dec 9
Total with taxes and fees
High Tide Haven Suite
Exterior
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown
10.0 out of 10, Exceptional, (12)
"Kayaks were a great plus! Ideal spot for a small family with easy access to the the beautiful Chester River. Our grandchildren had a blast, visiting the pigs, chickens, and sheep that were within easy walking distance."
United States
Douglas N.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Property grounds
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Rock Hall
10.0 out of 10, Exceptional, (29)
"I've stayed at many bnbs and this one felt the most luxurious/resort-like! Many comforts and homey touches. Close enough to walk places, far enough for peace and quiet. "
United States
Julie L.
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Fridge, microwave, oven, stovetop
Waterfront! Private Dock, Boat Tie-Up & Near Town

Waterfront! Private Dock, Boat Tie-Up & Near Town

Rock Hall
10.0 out of 10, Exceptional, (2)
"A beautiful spot."
United States
Laura S.
Waterfront! Private Dock, Boat Tie-Up & Near Town
Dining
Blue Heron Farm Waterfront Chalet

Blue Heron Farm Waterfront Chalet

Chestertown
10.0 out of 10, Exceptional, (1)
"We had an amazing stay on this picturesque slice of the Eastern Shore. The house is perfectly situated for stunning sunsets with ample outdoor space. We loved being able to cook out dinner while taking in wildlife and the water.Ben, our host, was quick to respond to questions and left a super helpful binder of suggestions. "
United States
Amy G.
Blue Heron Farm Waterfront Chalet
Beach nearby, sun loungers, beach towels
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Betterton
9.8 out of 10, Exceptional, (46)
"Beautiful, clean, quirky spot. We loved relaxing on the porch overlooking the water. Would definitely recommend and hope to visit again."
United States
Paige J.
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach towels
Peaceful getaway convenient to local amenities including beach, boating & food

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

Rock Hall
9.8 out of 10, Exceptional, (119)
"Great place, calming vibe, located in the middle of everything you may need. "
United States
Kim
Peaceful getaway convenient to local amenities including beach, boating & food
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.
View all properties

Great weekend hotel deals in Kent County, MD

Showing deals for:Dec 19 - Dec 21

Image gallery for Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Beach nearby, sun loungers, beach towels

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Betterton
9.8/10Exceptional (46 reviews)
7% off
$342 nightly
Price is $1,010
Total with taxes and fees
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
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
"Amazing view! "
Ashley 1-night trip
Posted 11 hours ago
The Royal Sonesta Harbor Court Baltimore

Explore a world of travel with Expedia