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

First Floor Studio Apartment in Historic Chestertown

Cass-N-Reel Luxury Houseboat

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

BAYSIDE BUNGALOW

Waterfront Oasis w/ Private Dock, 3BR/2BA

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

Large 2 bedroom house with private parking in a nice neighborhood

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Floating 2 bed 2 bath condo stunning views of the bay

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
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.
Top Holiday Rental Destinations
More accommodation in Chestertown
Top 20 Chestertown Hotels
More destinations for you
- Hotels in Anaheim
- Hotels in Aspen
- Honolulu Apartment Hotels
- Hotels in Monterey
- Hotels in Snowmass Village
- Hotels in Scotland
- Hotels in Lisbon
- Hotels in Lynbrook
- Hotels in Glenelg
- Hotels in California
- St. George Pet Friendly Hotels
- Hotels in Honolulu
- Hagerstown Luxury Hotels
- Hotels in Deal Island
- Hotels in Palm Springs
- Hotels in Santa Barbara
- Hotels in Richlands
- Hotels in Wolf
- Hotels in Sedona
- Hotels in Kailua-Kona
- Hotels in San Diego
- Hotels in Jackson
- Hotels in Eucha