Holiday Rentals in Chestertown
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Holiday Rentals 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
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Historic Annapolis Home 1.5 blocks from center of town.
Chesapeake Houseboat Getaway on Kent Island, Maryland
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Relax on Kent Island in 3 Bedroom Home w/Waterview
Cass-N-Reel Luxury Houseboat
Entire House by the Fells Point, JHU.
Captivating Chesapeake experience
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beautiful, spacious, quiet waterfront house!
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
5-bedroom vacation home 5 minutes from historic Charlestown
Other types of properties in Chestertown you may be interested in
Red Roof Inn & Suites Chestertown
Holiday Accommodation Chestertown
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Chestertown are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Chestertown itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Chestertown holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Chestertown, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Chestertown with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.