Book Holiday Homes in Chestertown
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Featured Holiday Homes in Chestertown
Pet-Friendly Home on Chester River w/ Dock!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Waterfront family resort Lodge with private pier, game room and bar
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Relax on Kent Island in 3 Bedroom Home w/Waterview
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
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 | 417 Holiday Homes |
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Lowest Price | NZ$135 |
Highest Price | NZ$733 |
Popular accommodation | Pet-Friendly Home on Chester River w/ Dock!, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning, Charming garden row home, easy 4 block walk to the heart of Annapolis., Waterfront family resort Lodge with private pier, game room and bar, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, A waterfront gem with dock, kayaks great water views. Sleeps up to 12., Relax on Kent Island in 3 Bedroom Home w/Waterview, 421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking! |
More accommodations in Chestertown
Top trending hotels in Chestertown
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Sagamore Pendry Baltimore
More ways to explore Chestertown
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^Subject to availability and chosen travel dates.