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Find Hotels & Resorts for Couples in Chestertown, MD from CA $86

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Check availability on Chestertown Hotels & Resorts for Couples

Top Chestertown Hotels & Resorts for Couples

Our top choices for Chestertown adventure hotels

Hampton Inn Baltimore/White Marsh
Exterior

Hampton Inn Baltimore/White Marsh

2.5 star property
7.6 out of 10, Good, (1001)
"Clean area clean rooms friendly staff"
The price is CA $121
CA $140 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn Baltimore/White Marsh
Hilton Garden Inn Baltimore/White Marsh
Exterior

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
7.8 out of 10, Good, (1000)
"Great place to stay highly recommend it "
The price is CA $141
CA $163 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Garden Inn Baltimore/White Marsh
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (111)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is CA $229
CA $305 total
includes taxes & fees
Aug 24 - Aug 25
Kent Island Resort
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (98)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is CA $137
CA $220 total
includes taxes & fees
Aug 25 - Aug 26
First Floor Studio Apartment in Historic Chestertown
Waterfront Retreat with Private Dock and Beach
Beach

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 CA $312
CA $519 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront Retreat with Private Dock and Beach
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!"
The price is CA $262
CA $704 total
includes taxes & fees
Aug 24 - Aug 25
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, (193)
"Great place close to eveything"
The price is CA $86
CA $284 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Fells Point Gem / In The Heart of Fells Point
Hidden Fells Point Gem / Private Courtyard Patio
Marina

Hidden Fells Point Gem / Private Courtyard Patio

9.6 out of 10, Exceptional, (87)
"Property is clean and efficiently designed, tastefully decorated and located in a safe, walkable area.I would recommend this location to anyone wanting to visitBaltimore."
The price is CA $86
CA $284 total
includes taxes & fees
Aug 25 - Aug 26
Hidden Fells Point Gem / Private Courtyard Patio
Exclusive Sunken Living Room Soaring Exposed Brick
Interior

Exclusive Sunken Living Room Soaring Exposed Brick

10.0 out of 10, Exceptional, (5)
"Our stay was absolutely wonderful! The amenities that Matthew provided were great -- there were mints, lollypops, and granola bars for each of us upon arrival. The space is incredible! From the Master Suite with a king-sized bed that was adjustable to the other bedrooms that were comfortable and cozy. Also, we loved the small details, like the beautiful paintings and decorations, plus the "Baltimore Bucket List" to check-off. Everything was clean and neat, and anytime we had a question, Matthew...
The price is CA $236
CA $524 total
includes taxes & fees
Aug 24 - Aug 25
Exclusive Sunken Living Room Soaring Exposed Brick
Cozy 2br home w/ parking in downtown Annapolis
Marina

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (70)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
The price is CA $243
CA $531 total
includes taxes & fees
Sep 9 - Sep 10
Cozy 2br home w/ parking in downtown Annapolis
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.

Top Chestertown Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Stayed for a baseball tournament and was pleased with everything from check in, to check out. Clean, spacious and everything in working order. Would stay again. "
Patrick 2-night trip
Posted 3 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South

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.