Book Holiday Homes in Chestertown
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Featured Holiday Homes in Chestertown

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Captivating Chesapeake experience

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

Historic Annapolis Home 1.5 blocks from center of town.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Entire House by the Fells Point, JHU.

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

PERFECT LOCATION in the heart of history
Chestertown Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chestertown vacation homes are the perfect way for you to wing it.
Holiday houses in Chestertown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chestertown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chestertown adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chestertown with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chestertown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Chestertown Holiday Homes essential information
Accommodation | 528 Holiday Homes |
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Lowest Price | AU$121 |
Highest Price | AU$417 |
Popular accommodation | Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , 240' Private Beachfront @Kent Island Love Point - Great for Large Groups, Captivating Chesapeake experience, ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Historic Annapolis Home 1.5 blocks from center of town., Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Entire House by the Fells Point, JHU., Steps to USNA Gate 3 at historic Gatehouse, on-site parking, PERFECT LOCATION in the heart of history |
Top Locations for Holiday Homes in Chestertown
More accommodations in Chestertown
Top trending hotels in Chestertown

Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

The Lodge at Great Oak Landing

Historic Inns of Annapolis
More ways to explore Chestertown
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.