Search Chestertown Holiday Homes from AU$127

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.

Featured Holiday Homes in Chestertown

Don't see what you're looking for?
See all available properties in Chestertown
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Holiday Accommodation Chestertown

Get the Lowdown on Chestertown Holiday Homes


How much is a holiday home in Chestertown?

Depending on when you visit, you can score a holiday home in Chestertown for as little as AU$127 per night. Prices vary by property class, amenities, and location, all of which you can quickly sort through on our handy search page.


How do I find the best price for a holiday home in Chestertown?

Discover exclusive deals on Chestertown house rentals when you book with Wotif. Once you enter the dates of your trip and number of travellers (Girls’ trip? Family getaway? We’ve got you covered.), filter the results by guest rating, budget, property class, number of bedrooms, amenities, and more. You can also use the map feature to zoom in on the neighbourhood or to view several rentals at once.


Why should I book a holiday home in Chestertown?

Because there’s nothing better than having a private place to call your home away from home while exploring Chestertown. When you book a holiday house in Chestertown, you can indulge in a variety of sweet amenities and truly relax in your own space.


What is the best time to stay in a holiday home in Chestertown?

Pack your bags and head to your rental house in , the most popular time to visit. If smaller crowds are your thing, book a holiday home in the off-season, around , when you may get more of a bargain.


How many holiday homes are available for rent in Chestertown?

Whether you’re adventuring to Chestertown for the first time or planning a return trip to your favourite spot, pick from 402 unique holiday homes in Chestertown.


What amenities are available in a private holiday home?

You’ll often find most amenities you’re looking for, such as a private pool or hot tub, parking on the premises, a full-service kitchen or kitchenette, laundry and Wi-Fi. If your companion has four legs, book a pet-friendly Chestertown accommodation so your furry pal is as comfy and cosy as can be. Keep in mind that the price of your rental will depend on how luxe the amenities are.


Why should I book a holiday home with Wotif?

You’ll find spectacular deals, book now and pay later discounts, and a massive inventory of one-of-a-kind house rentals. Save big bucks when you book your Chestertown car hire and accommodation together into a Chestertown holiday package. Our Price Promise means that if you find a lower price online up to 24 hours before check-in, we’ll match it and refund the difference. Do the right thing and book your Chestertown holiday house with Wotif.


What are the cancellation and flexibility options?

We understand that plans change, so we offer thousands of holiday homes that have free cancellations. To be sure your rental can be cancelled for a full refund, filter your search by “free cancellation”. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.

Chestertown Holiday Homes essential information

Accommodation
402 Holiday Homes
Lowest Price
AU$127
Highest Price
AU$641
Popular accommodation
Directly Across from Gate One & Steps from the Waterfront , Elegant Urban Retreat in Canton Baltimore, Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Charming garden row home, easy 4 block walk to the heart of Annapolis., Charming Historic Townhouse Steps From USNA, Idyllic Pasadena Retreat with Garden + Hot Tub!, Charming brick home with patio, WiFi, AC, & W/D - walk to everything, Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard, Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets, Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!, Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.

Top trending hotels in Chestertown

^Eligibility requirements and conditions apply.