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!
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
The Heron's Nest at Atlantic Marina
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Captivating Chesapeake experience
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Luxury Waterfront Home Built for Entertaining!
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
Relax on Kent Island in 3 Bedroom Home w/Waterview
Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Cass-N-Reel Luxury Houseboat
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Waterfront Oasis of Annapolis Star
Other types of properties in Chestertown you may be interested in
Comfort 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.