Chestertown Holiday Homes
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Featured Holiday Homes in Chestertown

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

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

Historic Row Home 1 Block from Gate 1 at USNA!

Charming Historic Annapolis Home With Two Off-street Parking Places!

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Waterfront house with amazing views. Top of the Chesapeake

Nancy’s Touch, A Waterfront Paradise!

Large 2 bedroom house with private parking in a nice neighborhood

Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.

Entire Townhouse in Rock Hall
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.
Chestertown Holiday Homes essential information
Accommodation | 483 Holiday Homes |
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Lowest Price | NZ$148 |
Highest Price | NZ$1,220 |
Popular accommodation | Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Historic Row Home 1 Block from Gate 1 at USNA!, Charming Historic Annapolis Home With Two Off-street Parking Places!, Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !, Waterfront house with amazing views. Top of the Chesapeake, Nancy’s Touch, A Waterfront Paradise!, Large 2 bedroom house with private parking in a nice neighborhood, Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented., Entire Townhouse in Rock Hall, Timeless Charm Meets Modern Comfort, Waterfront Estate w Private Pier, Game Room & Bar |
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Red Roof Inn & Suites Chestertown
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