Destination guide

Take in the waterfront beauty of Chester

The island views and surrounding scenery provide a peaceful ambiance to your vacation home in Chester. This city's boating, biking and seafood restaurants draw many visitors. William Paca House and Maryland State House are just a couple of the must-sees in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.


Activities and attractions in Chester

Are you searching for attractions to visit in the city? Venture out of your cozy vacation rental and check out everything that Chester has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Queenstown Harbor Golf Club (6.5 mi / 10.4 km)
  • U.S. Naval Academy Golf Club (10.4 mi / 16.7 km)
  • St. Michaels Winery (12.3 mi / 19.7 km)
  • Hog Neck Golf Course (14.9 mi / 23.9 km)
Natural features

Exploring the natural features in Chester

Whether you're an outdoor enthusiast or just want to take in the scenery, Chester is a great place to spend some time outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Kent Island (2.1 mi / 3.4 km)
  • Sandy Point State Park (8.3 mi / 13.4 km)
  • Maryland Quiet Waters Park (12 mi / 19.3 km)
  • Ferry Park (12.8 mi / 20.6 km)
  • Shadyside Park (14.7 mi / 23.6 km)
How to get there

Transportation options to and around Chester

The nearest airport is in Easton, MD (ESN-Easton - Newnam), located 15.1 mi (24.3 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), which is 26.1 mi (42 km) away.

Where to stay around Chester?

Our 2019 property listings offer a large selection of 165 vacation rentals near Chester. From 106 Houses to 11 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chester for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Chester?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chester:

  • Historic District: 110 vacation rentals
  • Eastport: 160 vacation rentals
  • Arundel on the Bay: 18 vacation rentals
  • Homewood: 59 vacation rentals
  • Naval Academy: 115 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Chester?

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

  • Chesapeake Exploration Center: 653 vacation rentals
  • Chesapeake Bay Bridge: 640 vacation rentals
  • Sandy Point State Park: 630 vacation rentals
  • U.S. Naval Academy: 667 vacation rentals
  • Maryland Quiet Waters Park: 689 vacation rentals

But there are many other points of interest around Chester listed on HomeAway 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 Chester?

Yes, of course. HomeAway has 106 Houses in Chester. Our other popular types of vacation rentals in Chester include:

  • Condos/Apartments: 11 rentals available
  • Cabins: 21 rentals available
  • Cottages: 21 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Chester?

Yes, you can select your preferred vacation rental with pool among our 59 vacation rentals with pool available in Chester. Please use our search bar to access the selection of vacation rentals available.

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