Top Chesapeake City beach rentals - Maryland

Explore Chesapeake City beach rentals

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Sleeps 15 · 7 bedrooms · 5+ bathrooms

12 Bedroom Waterfront Historic 1920 Mansion! Pool, hot tub and 400 acres!

Sleeps 30 · 12 bedrooms · 8+ bathrooms

Charming 4-Bedroom Cottage - Vineyard Views & Waterfront Tasting Room & Resort

Sleeps 8 · 4 bedrooms · 2+ bathrooms

Top rated beach rentals - Chesapeake City

Premier Host

Incredible view and hospitality!

House is easy to find, backed right up to the water so you get to wake up to gorgeous sunsets! The home is well furnished with everything you could need and on top of that it’s beautiful. Located near some great seafood restaurants and local shops.

Destiny C.

Stayed Feb 2021

Find spaces that suit your style

House

Condo/Apartment

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

Are there any beach holiday rentals in Chesapeake City?

Choose one of our 14 beach holiday rentals in Chesapeake City and you'll have the ideal base for your next trip to the coast. Arundel, Williamsburg and Yorkshire are among this city's most popular areas to stay.

How much does it cost to stay in a beach holiday rental in Chesapeake City?

Where you stay, when you want to travel and your trip length will determine how much you pay for a beach holiday rental in Chesapeake City. Enter your travel dates on Stayz to compare your options and then select one that's perfect for your seaside escape.

Where can I book a Chesapeake City beach holiday rental with great views?

Stay at a beach holiday rental in Chesapeake City and you'll be opening your front door to impressive vistas. Some of our more popular rental houses here boast views of historic areas.

What are the top things to do in Chesapeake City?

Get your Chesapeake City getaway off to an amazing start with a visit to top-rated attractions like Lums Pond State Park, Kirkwood Soccer Complex and Elk Neck State Park. Stay in a Stayz beach holiday rental with the family and then discover this destination's wonders together.

Why should I book my beach holiday rental with Stayz?

No sharing your space, no uncomfortable encounters with people you don't know. When you stay in a Stayz beach holiday rental, you get the whole place for your use only. Need to amend or cancel your itinerary? Our flexible cancellation policies mean you can book your rental house with total peace of mind.