Discover a selection of 36 holiday rentals in Chesapeake City, MD, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 195 per night, and houses and flats & apartments are popular options for a stay in Chesapeake City. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chesapeake City
Destination guide

The waterfront setting of Chesapeake City is ready to explore

The area's history and museums are just some of the reasons to come on holiday to Chesapeake City. Travellers appreciate the restaurants in this welcoming city. With a holiday 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 cosy holiday rental and experience everything that makes Chesapeake City a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 holiday in Chesapeake City. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • 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

Travelling to and around Chesapeake City

The nearest airport is in Baltimore, MD (MTN-Martin State), located 32.9 mi (53 km) from the city centre. 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.

Can I find a vacation rental around Chesapeake City?

Yes, our 2021 property listings offer a large selection of 36 vacation rentals near Chesapeake City. From 30 houses to 3 flats & apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chesapeake City for a holiday or a weekend are on Vrbo.

Can I rent Houses in Chesapeake City?

Yes, of course. Vrbo UK has 30 Houses in Chesapeake City. Our other popular types of vacation rentals in Chesapeake City include:

  • Flats: 3 rentals available
  • Studios: 3 rentals available
  • House: 28 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.