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Top Cities in Kent County

HotelsHotels

Chestertown

Chestertown

Check prices for these dates

Tonight
25 Jun - 26 Jun
Tomorrow
26 Jun - 27 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

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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, (772)
"Comfortable room, friendly staff. "
The price is NZ$210
includes taxes & fees
24 July - 25 July
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
7.8 out of 10, Good, (52)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"
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
7.4 out of 10, Good, (368)
"Was a decent place to stay for the price. "
The price is NZ$126
includes taxes & fees
9 July - 10 July
Red Roof Inn & Suites Chestertown
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (50)
"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."
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 NZ$126
includes taxes & fees
26 June - 27 June
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 NZ$287
includes taxes & fees
29 June - 30 June
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, (14)
"Fantastic accommodations! Many amenities! Friendly hostess! "
The price is NZ$197
includes taxes & fees
26 June - 27 June
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, (88)
"Very pretty location. Few minutes drive to town center."
The price is NZ$265
includes taxes & fees
26 June - 27 June
First Floor Studio Apartment in Historic Chestertown
BAYSIDE BUNGALOW
Sauna

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (39)
"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 NZ$501
includes taxes & fees
26 June - 27 June
BAYSIDE BUNGALOW
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, (8)
"Perfection"
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (20)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
The price is NZ$621
includes taxes & fees
7 July - 8 July
Waterfront Retreat with Private Dock and Beach
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Dining

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (35)
"Was a great vacation hope to come back next year!"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (34)
"We love this place and would stay here again in a heartbeat. Beautifully decorated with so many details and touches that make it extra special. Such a well done lovely property!!!"
Historic Downtown Garden Oasis with Private Patio
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
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
Marina

Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.

10.0 out of 10, Exceptional, (7)
"Property was extremely well kempt. It was beautiful. We enjoyed ourselves there and would recommend it to others."
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

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

10.0 out of 10, Exceptional, (2)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
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 NZ$612
includes taxes & fees
24 July - 25 July
Grandma’s Cottage will wrap around you like a warm hug
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

9.6 out of 10, Exceptional, (40)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
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!
Serene Waterfront Cottage with dock and gorgeous views.
Fridge, microwave, dishwasher, coffee/tea maker

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (37)
"A must book!"
Serene Waterfront Cottage with dock and gorgeous views.
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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