Search Chestertown Holiday Homes from AU$584

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Featured Holiday Homes in Chestertown

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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$584 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 418 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
418 Holiday Homes
Lowest Price
AU$584
Highest Price
AU$1,037
Popular accommodation
Waterfront w/private pier, pool, Hot Tub, kayaks and in town., Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Freshly renovated 3-story home 1 block from USNA!, Pet-Friendly Home on Chester River w/ Dock!, Walk to Lake & Boat Ramp: Central Gem in Annapolis, Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning, Charming Historic Townhouse Steps From USNA, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Glen Burnie Escape - Pet friendly with easy access to multiple attractions., Baseball Lovers Paradise!, Cozy 5 bedroom house with attached guest suite
^Eligibility requirements and conditions apply.