Holiday Rentals in Chestertown
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Unlock member prices with Mates Rates
You could save 10% or more on over 100,000 hotels right now.
Check rental availability in Chestertown
Holiday Rentals in Chestertown
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Chesapeake Houseboat Getaway on Kent Island, Maryland
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Relax on Kent Island in 3 Bedroom Home w/Waterview
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Captivating Chesapeake experience
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Cass-N-Reel Luxury Houseboat
Beautiful, spacious, quiet waterfront house!
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.