Chestertown Holiday Homes
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
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Holiday Homes in Chestertown

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

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

Captivating Chesapeake experience

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Historic Annapolis Home 1.5 blocks from center of town.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Entire House by the Fells Point, JHU.

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

PERFECT LOCATION in the heart of history

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Step into History: Charming Fells Point Retreat

Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning
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 | 528 Holiday Homes |
---|---|
Lowest Price | NZ$138 |
Highest Price | NZ$773 |
Popular accommodation | Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , 240' Private Beachfront @Kent Island Love Point - Great for Large Groups, Captivating Chesapeake experience, ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Historic Annapolis Home 1.5 blocks from center of town., Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Entire House by the Fells Point, JHU., Steps to USNA Gate 3 at historic Gatehouse, on-site parking, PERFECT LOCATION in the heart of history, Bay Breeze - Charming 3BR Waterfront Home on the Chester River, Step into History: Charming Fells Point Retreat, Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning |
Top cities with Holiday Homes
Top trending hotels in Chestertown

Red Roof Inn & Suites Chestertown
^Eligibility requirements and conditions apply