Chestertown Holiday Homes
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Featured Holiday 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
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 | 534 Holiday Homes |
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Lowest Price | NZ$102 |
Highest Price | NZ$813 |
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. |
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