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Find Hotels & Resorts for Couples in Chestertown, MD

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Check availability on Chestertown Hotels & Resorts for Couples

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Oct 1 - Oct 2
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Oct 2 - Oct 3
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Oct 3 - Oct 5
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Oct 10 - Oct 12

Top Chestertown Hotels & Resorts for Couples

Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1007)
"Very good breakfast options Convenient parking Clean room Friendly staff"
$88 nightly
The price is $99
Oct 8 - Oct 9
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Hilton Garden Inn Baltimore/White Marsh
Exterior

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
7.8 out of 10, Good, (1027)
"Nice clean hotel with very friendly staff"
$102 nightly
The price is $117
Oct 5 - Oct 6
Total with taxes and fees
Hilton Garden Inn Baltimore/White Marsh
Hampton Inn Baltimore/White Marsh
Exterior

Hampton Inn Baltimore/White Marsh

2.5 star property
7.8 out of 10, Good, (1019)
"Really enjoyed my stay, the staff were nice."
$99 nightly
The price is $115
Oct 8 - Oct 9
Total with taxes and fees
Hampton Inn Baltimore/White Marsh
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (101)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
$144 nightly
The price is $159
Oct 6 - Oct 7
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
$225 nightly
The price is $246
Oct 19 - Oct 20
Total with taxes and fees
Kent Island Resort
Hampton Inn Baltimore/Glen Burnie
Free daily continental breakfast

Hampton Inn Baltimore/Glen Burnie

2.5 star property
8.2 out of 10, Very Good, (1001)
"The staff was very nice, the beds were comfortable, the breakfast selections were excellent. "
$116 nightly
The price is $132
Oct 26 - Oct 27
Total with taxes and fees
Hampton Inn Baltimore/Glen Burnie
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
$282 nightly
The price is $311
Oct 5 - Oct 6
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"This rental is amazing and highly recommended!! Beautiful decor! Very clean! Great outside hang out area! Awesome hosts!! Thank you so much for a great stay! "
$413 nightly
The price is $438
Oct 6 - Oct 7
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Charming Pet-Friendly Stay - Near Bay & Beaches.
Interior

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (3)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
$484 nightly
The price is $552
Oct 6 - Oct 7
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
Cozy Fells Point Gem / In The Heart of Fells Point
Marina

Cozy Fells Point Gem / In The Heart of Fells Point

9.8 out of 10, Exceptional, (196)
"Great place close to eveything"
$178 nightly
The price is $206
Oct 6 - Oct 7
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
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
"Great stay"
Diedre 2-night trip
Posted 2 days ago
Best Western Plus Hotel & Conference Center

Frequently asked questions

Why book your hotel for couples in Chestertown with Expedia?
Expedia has some excellent hotels for couples, so go ahead and spoil yourselves in Chestertown. If you have a set budget, click on how much you want to spend and your preferred hotel star rating. Whatever your getaway looks like, we'll help you find a pad that'll make both your pocket and partner smile!
How can I find cheap hotels for couples in Chestertown?
Expedia can help you easily source cheap hotels for couples in Chestertown. Use our filter tool to select budget, star rating and amenities to tailor your search results and reserve the perfect place to escape with your partner in just a few clicks.
What is there to do in Chestertown near my hotel for couples?
Once you've unpacked and settled in, head out and explore the wonderful things Chestertown has on offer. Historical Society of Kent County Maryland is a top attraction to add to your itinerary.

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Explore a world of travel with Expedia