Chestertown Holiday Homes
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Featured Holiday Homes in Chestertown

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Large 2 bedroom house with private parking in a nice neighborhood

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

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

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Location is perfect and a big bonus we have our own parking at the home!

BEAUTIFULLY FURNISHED COZY ENSUITE 2BR3 BA IN UPPER FELLS POINT, BALTIMORE

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

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
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 | 409 Holiday Homes |
|---|---|
Lowest Price | NZ$130 |
Highest Price | NZ$2,000 |
Popular accommodation | Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Large 2 bedroom house with private parking in a nice neighborhood, Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Charming garden row home, easy 4 block walk to the heart of Annapolis., Location is perfect and a big bonus we have our own parking at the home!, BEAUTIFULLY FURNISHED COZY ENSUITE 2BR3 BA IN UPPER FELLS POINT, BALTIMORE, Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !, *** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay, Waterfront Oasis w/ Private Dock, 3BR/2BA, 200 steps to the beach! |
Top trending hotels in Chestertown

Comfort Inn & Suites Chestertown
Top cities with Holiday Homes
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