Find Hotels with a View in Chestertown, MD

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Our top choices for Chestertown a view hotels

Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Dec 15 - Dec 16
Total with taxes and fees
The Lodge at Great Oak Landing
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 15 - Dec 16
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Reception
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
$179 nightly
The price is $195
Dec 15 - Dec 16
Total with taxes and fees
Kent Island Resort
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (932)
"It was very comfortable and clean"
United States
Maria
$87 nightly
The price is $97
Jan 3 - Jan 4, 2026
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Restaurant
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (216)
"We reserved 4 rooms, and arrived around noon. We didn't think, with early arrival, that our rooms would be ready, but they were! The staff was extremely accommodating and friendly. Our rooms were immaculate, beds comfy. It was a great stay for visiting family in the area. "
United States
Stephen
$84 nightly
The price is $94
Dec 28 - Dec 29
Total with taxes and fees
Courtyard Aberdeen at Ripken Stadium
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1000)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
$83 nightly
The price is $93
Dec 22 - Dec 23
Total with taxes and fees
Best Western Kent Narrows Inn
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
"We stayed overnight, coming to meet some people for a business meeting. Monica at the front desk provided great customer service and was extremely helpful in accommodating us. "
United States
Anthony
$103 nightly
The price is $115
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (674)
"Great view, good ambiance all around"
United States
Dianne
$116 nightly
The price is $129
Dec 14 - Dec 15
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
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

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 15 - Dec 16
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Printers
Hudson house

Hudson house

Hudson house
3.5 star property
Canton
$283 nightly
The price is $333
Dec 13 - Dec 14
Total with taxes and fees
Hudson house
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 Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Clean room, great location, very friendly and helpful staff"
Beverly 1-night trip
Posted 3 days ago
Best Western Plus Hotel & Conference Center

Frequently asked questions

Why book your hotel with views in Chestertown with Expedia?
Wherever you want to be in Chestertown, Expedia can help you locate the best hotels with views. On the lookout for something luxurious or low cost, a property that comes with a certain amenity, or one that's in a trendy neighborhood? Use Expedia's search filters to find your ideal pad. Also want an amazing deal? Well, we have those too!
What is there to do in Chestertown near my hotel with views?
The ideal travel accessory is a well-planned itinerary. Historical Society of Kent County Maryland is a wonderful place to kick off your sightseeing in Chestertown.

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