Where to stay around Chester, MD?

Our 2019 property listings offer a large selection of 175 vacation rentals near Chester. From 110 Houses to 21 Cabins, 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 VRBO.

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: 112 vacation rentals
  • Eastport: 152 vacation rentals
  • Bay Ridge: 34 vacation rentals
  • Homewood: 62 vacation rentals
  • Murray Hill: 101 vacation rentals

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

Can I rent Houses in Chester?

Yes, of course. VRBO has 110 Houses in Chester. Our other popular types of vacation rentals in Chester include:

  • Cabins: 21 rentals available
  • Cottages: 21 rentals available
  • Bungalows: 21 rentals available

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

Can I find a vacation rental with pool in Chester?

Yes, you can select your prefered vacation rental with pool among our 62 vacation rentals with pool available in Chester. Please use our search bar to access the selection of vacation rentals available.

    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)

    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)