Discover a selection of 32 vacation rentals in Chesapeake City, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $160 per night, and houses and condos are popular options for a stay in Chesapeake City. Either way, you'll find a rental for everyone's needs.
Destination guide

The waterfront setting of Chesapeake City is ready to explore

The area's history and museums are just a few of the reasons to vacation in Chesapeake City. Travelers appreciate the restaurants in this welcoming city. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.


Activities and attractions in Chesapeake City

Are you searching for attractions to see while you're in town? Venture out of your cozy vacation rental and experience everything that makes Chesapeake City a fun spot to vacation. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Back Creek Golf Club (4.5 mi / 7.3 km)
  • Frog Hollow Golf Club (7.5 mi / 12.1 km)
  • Bulle Rock Golf Course (15.6 mi / 25.2 km)
  • Mount Felix Vineyard & Winery (15.7 mi / 25.3 km)
  • Dove Valley Winery (15.8 mi / 25.4 km)
  • Plumpton Park Zoo (16.5 mi / 26.5 km)
Natural features

Exploring the natural features in Chesapeake City

Whether you're an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Chesapeake City. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Elk Neck State Park (7.2 mi / 11.6 km)
  • Lums Pond State Park (7.9 mi / 12.7 km)
  • Glendale Park (12.7 mi / 20.4 km)
  • Dickey Park (12.9 mi / 20.8 km)
  • Lewis Park (13 mi / 21 km)
  • Kells Park (13.1 mi / 21.1 km)
How to get there

Traveling to and around Chesapeake City

The nearest airport is in Baltimore, MD (MTN-Martin State), located 32.9 mi (53 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), which is 49.3 mi (79.3 km) away.

How many vacation rentals are available around Chesapeake City, MD?

Our 2020 property listings offer a large selection of 32 vacation rentals around Chesapeake City. From 25 house rentals to 4 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Chesapeake City?

Vrbo offers a large selection of vacation rentals near lovely places in Chesapeake City. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • C and D Canal Museum: 61 vacation rentals
  • University of Delaware: 85 vacation rentals
  • Lums Pond State Park: 62 vacation rentals
  • Havre de Grace Promenade: 54 vacation rentals
  • Historical Society of Cecil County: 72 vacation rentals

But there are many other points of interest around Chesapeake City listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Chesapeake City?

Yes, of course. Vrbo has 25 Houses in Chesapeake City. Our other popular types of vacation rentals in Chesapeake City include:

  • Condos/Apartments: 4 rentals available
  • Studios: 4 rentals available
  • Apartment: 4 rentals available

Can I find a vacation rental with pool in Chesapeake City?

Yes, you can select your preferred vacation rental with pool among our 6 vacation rentals with pool available in Chesapeake City. Please use our search bar to access the selection of vacation rentals available.