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Top Cities in Kent County

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Chestertown

Chestertown

Check prices for these dates

Tonight
23 Jul - 24 Jul
Tomorrow
24 Jul - 25 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

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Top Hotels in Kent County

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (785)
"It was a clean comfortable spot to rest for the night. "
The price is €108
includes taxes & fees
17 Aug - 18 Aug
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, (55)
"Great place to get some quiet rest by the water"
The price is €125
includes taxes & fees
6 Aug - 7 Aug
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, (379)
"Good location."
The price is €72
includes taxes & fees
6 Aug - 7 Aug
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. "
Inn at Huntingfield Creek
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 €60
includes taxes & fees
24 Jul - 25 Jul
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 €147
includes taxes & fees
11 Aug - 12 Aug
Mariners Motel
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
The price is €226
includes taxes & fees
31 Jul - 1 Aug
Inn at Haven Harbour
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)
"Fantastic accommodations! Many amenities! Friendly hostess! "
The price is €105
includes taxes & fees
28 Jul - 29 Jul
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, (91)
"Very pretty location. Few minutes drive to town center."
The price is €139
includes taxes & fees
4 Aug - 5 Aug
First Floor Studio Apartment in Historic Chestertown
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 €257
includes taxes & fees
27 Jul - 28 Jul
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
BAYSIDE BUNGALOW
Sauna

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (42)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is €264
includes taxes & fees
24 Jul - 25 Jul
BAYSIDE BUNGALOW
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (21)
"I stayed with 3 friends and it was lovely! The apartment was clean and tidy. The view was spectacular. The host was very communicative and kind leading up to and during our stay. There are great restaurants and things to do in the area as well. "
The price is €331
includes taxes & fees
24 Jul - 25 Jul
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 €321
includes taxes & fees
24 Jul - 25 Jul
Grandma’s Cottage will wrap around you like a warm hug
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (35)
"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
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!
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
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
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
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Outdoor dining

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

10.0 out of 10, Exceptional, (46)
"Cool house within walking distance to beach, restaurant and marinas"
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is €373
includes taxes & fees
27 Jul - 28 Jul
Bayside Cottage steps from Rock Hall Harbor
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.
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Top Kent County Hotel Reviews

Hyatt Place Baltimore Inner Harbor

Hyatt Place Baltimore Inner Harbor

10/10 Excellent
"Loved this hote k breakfast was great "
A 3-night trip
Posted 18 hours ago
Hyatt Place Baltimore Inner Harbor