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Top Cities in Kent County

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

Chestertown

Check prices for these dates

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

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Compare 2,378 hotels in Kent County with room rates, reviews, and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
Welcome to our reception area, where friendly staff are available to assist with your stay.

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 ￥16,143
￥17,919 total
includes taxes & fees
Aug 17 - Aug 18
Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing
Surrounded by a tranquil lake, this serene setting features a cozy fire pit amidst a picturesque landscape.

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (59)
"Great place to get some quiet rest by the water"
The price is ￥19,440
￥21,578 total
includes taxes & fees
Aug 10 - Aug 11
The Lodge at Great Oak Landing
Red Roof Inn & Suites Chestertown
Classic hotel room with a large bed, bedside tables, and a comfortable armchair.

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (384)
"Good location."
The price is ￥10,579
￥11,743 total
includes taxes & fees
Aug 20 - Aug 21
Red Roof Inn & Suites Chestertown
Inn at Huntingfield Creek
Relax on the lakeside deck with a comfortable lounge chair, surrounded by lush greenery.

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
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
10.0 out of 10, Exceptional, (2)
"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 ￥30,774
￥37,098 total
includes taxes & fees
Aug 12 - Aug 13
Inn at Haven Harbour
Driftwood Inn
Rows of rooms with stone facades and windows line the building's side.

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 ￥9,331
￥10,358 total
includes taxes & fees
Aug 11 - Aug 12
Driftwood Inn
Mariners Motel
Docked in the marina, a sleek yacht awaits your arrival.

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 ￥22,812
￥25,322 total
includes taxes & fees
Aug 10 - Aug 11
Mariners Motel
Guest Suite for up to 2 in a Victorian on the Chester River
Stunning two-story home with a gabled roof and inviting front porch.

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 ￥8,993
￥17,320 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!
Relax in a serene beach setting with a tranquil gazebo overlooking the ocean.

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

10.0 out of 10, Exceptional, (10)
"Perfection"
The price is ￥18,221
￥42,995 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
Relax by the pool surrounded by a tranquil golf course view.

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 ￥14,547
￥23,340 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 ￥29,388
￥43,923 total
includes taxes & fees
Aug 10 - Aug 11
BAYSIDE BUNGALOW
Waterfront Retreat with Private Dock and Beach
Guests can enjoy a serene lake view from the pier, surrounded by lush greenery.

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 ￥33,062
￥54,695 total
includes taxes & fees
Aug 17 - Aug 18
Waterfront Retreat with Private Dock and Beach
Grandma’s Cottage will wrap around you like a warm hug
Relax on the covered porch with a comfortable seating area featuring two chairs and a table.

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

The price is ￥33,062
￥61,524 total
includes taxes & fees
Aug 15 - Aug 16
Grandma’s Cottage will wrap around you like a warm hug
Knot's Landing, spacious Apt. downtown Rock Hall
Relax on the balcony with wicker sofas and a small table, taking in the view of the residential street below.

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!
Relax in a serene outdoor space with a round table and two chairs on a covered deck overlooking a natural landscape.

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
Guests can enjoy serene ocean views from this tranquil retreat.

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
Guests can enjoy breathtaking views of the calm body of water from the rocky outcrop.

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
Relax by the serene pool surrounded by lush greenery and vibrant flowers.

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
Fully equipped kitchen with a refrigerator, oven, microwave, and toaster.

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
Stroll through the serene garden, surrounded by lush plants and a majestic tree.

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (37)
"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.
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Top Kent County Hotel Reviews

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"A"
Craig 1-night trip
Posted 23 hours ago
Bally's Dover Casino Resort