Photo by Assya A

Find Hotels with a View in Chestertown, MD

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Hotels with a View

Check prices for these dates

Tonight
Jul 9 - Jul 10
Tomorrow
Jul 10 - Jul 11
This weekend
Jul 11 - Jul 13
Next weekend
Jul 18 - Jul 20

Top Chestertown Hotels with a View

First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (90)
"Very pretty location. Few minutes drive to town center."
$144 nightly
The price is $159
Jul 17 - Jul 18
Total includes taxes and fees
First Floor Studio Apartment in Historic Chestertown
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! "
$111 nightly
The price is $118
Jul 15 - Jul 16
Total includes taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
5-bedroom vacation home 5 minutes from historic Charlestown
View from property

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
$571 nightly
The price is $605
Jul 15 - Jul 16
Total includes taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
Vandiver Inn
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (502)
"Wonderful stay. Will stay here again!"
$140 nightly
The price is $157
Jul 28 - Jul 29
Total includes taxes and fees
Vandiver Inn
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (956)
"Great stay. We have stayed multiple times throughout the years and the quality has always been excellent."
$152 nightly
The price is $169
Jul 28 - Jul 29
Total includes taxes and fees
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (867)
"Great place"
$119 nightly
The price is $132
Jul 21 - Jul 22
Total includes taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very Good, (1000)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
$126 nightly
The price is $140
Jul 24 - Jul 25
Total includes taxes and fees
Best Western Kent Narrows Inn
Courtyard Aberdeen at Ripken Stadium
Lobby

Courtyard Aberdeen at Ripken Stadium

3.0 star property
8.6 out of 10, Excellent, (207)
"The staff was very friendly, easy and quick check-in. I would chose thus hotel again, very quiet. "
$93 nightly
The price is $104
Jul 27 - Jul 28
Total includes taxes and fees
Courtyard Aberdeen at Ripken Stadium
Travelodge by Wyndham Aberdeen
Exterior

Travelodge by Wyndham Aberdeen

2.0 star property
6.2 out of 10, (483)
"Dump"
$70 nightly
The price is $79
Jul 16 - Jul 17
Total includes taxes and fees
Travelodge by Wyndham Aberdeen
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Beach

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (28)
"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "
$283 nightly
The price is $300
Jul 13 - Jul 14
Total includes taxes and fees
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
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.

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!
How can I find cheap hotels with views in Chestertown?
To book your perfect cheap hotel with views in Chestertown, simply use our filter tool to refine your search by amenities, budget and star rating. You can also sort your results by price so that the most affordable stays appear at the top. Then, kick back and admire views worth pulling your camera out for!
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.