Search Chesapeake City Holiday Homes from AU$93

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 Chesapeake City

Don't see what you're looking for?
See all available properties in Chesapeake City
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 Chesapeake City

Get the Lowdown on Chesapeake City Holiday Homes


How much is a holiday home in Chesapeake City?

Depending on when you visit, you can score a holiday home in Chesapeake City for as little as AU$93 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 Chesapeake City?

Discover exclusive deals on Chesapeake City 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 Chesapeake City?

Because there’s nothing better than having a private place to call your home away from home while exploring Chesapeake City. When you book a holiday house in Chesapeake City, 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 Chesapeake City?

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 Chesapeake City?

Whether you’re adventuring to Chesapeake City for the first time or planning a return trip to your favourite spot, pick from 109 unique holiday homes in Chesapeake City.


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 Chesapeake City 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 Chesapeake City car hire and accommodation together into a Chesapeake City 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 Chesapeake City 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.

Chesapeake City Holiday Homes essential information

Accommodation
109 Holiday Homes
Lowest Price
AU$93
Highest Price
AU$910
Popular accommodation
2 Master Bedrooms each w/private full baths. Quick drive or walk to everything!, Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!, Captivating Chesapeake experience, Ultimate Retreat @ Papermill Rd, Home Away from Home - Local Shops, Restaurants & Grocery stores within 4 miles! , Luxurious and spacious townhome with all necessary amenities awaits your stay., Waterfront house with amazing views. Top of the Chesapeake, Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach, Top of the Chesapeake - Minutes from Historic Charlestown, Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!, Historic home in the heart of Main Street- walkable to shops and restaurants, This house is a 3 bedroom(s), 1.5 bathrooms, located in Port Deposit, MD.

Top trending hotels in Chesapeake City

^Eligibility requirements and conditions apply.