Vacation Homes in Chestertown
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Featured Vacation Homes in Chestertown

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Charming Historic Townhouse Steps From USNA

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

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Beautiful, spacious, quiet waterfront house!

Hidden Fells Point Gem / Private Courtyard Patio

Pet-Friendly Home on Chester River w/ Dock!

Relax on Kent Island in 3 Bedroom Home w/Waterview

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

BAYSIDE BUNGALOW
Top trending hotels in Chestertown

Sagamore Pendry Baltimore
Vacation Rentals in Chestertown
What kind of vacation do you want in Chestertown? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Chestertown that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Chestertown, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Chestertown Vacation Homes essential information
Accommodation | 518 Vacation Homes |
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Lowest Price | CA $85 |
Highest Price | CA $518 |
Popular accommodation | Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Charming Historic Townhouse Steps From USNA, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Beautiful, spacious, quiet waterfront house!, Hidden Fells Point Gem / Private Courtyard Patio, Pet-Friendly Home on Chester River w/ Dock!, Relax on Kent Island in 3 Bedroom Home w/Waterview, Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy, BAYSIDE BUNGALOW, Historic Annapolis Home 1.5 blocks from center of town. |