Destination guide

Take in the waterfront beauty of Chester

The island views and surrounding scenery provide a peaceful ambience to your holiday home in Chester. This city's boating, cycling and seafood restaurants draw many visitors. William Paca House and Maryland State House are just a couple of the must-see attractions 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 cosy holiday 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 centre:

  • 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 centre:

  • 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

Transport 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 centre. 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.

How many holiday rentals are available around Chester?

Our 2020 accommodation listings offer a large selection of 146 holiday lettings around Chester. From 99 houses to 21 cottages, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

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

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Chester:

  • Homewood: 37 holiday homes
  • Historic District: 71 holiday homes
  • Eastport: 96 holiday homes
  • West Annapolis: 18 holiday homes
  • Murray Hill: 67 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Chester? offers a large selection of holiday accommodations near great places in Chester. From travellers, the most popular points of interest to stay near are:

  • Pickering Creek Audubon Center: 208 holiday lettings
  • Maryland Quiet Waters Park: 500 holiday lettings
  • The Kunta Kinte Alex Haley Memorial: 508 holiday lettings
  • Sandy Point State Park: 431 holiday lettings
  • Cassinelli Winery and Vineyards: 82 holiday lettings

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

Can I rent Houses in Chester?

Yes, of course. offers 99 Houses in Chester. Our other popular types of Chester holiday rentals include:

  • Cottages: 21 self catering accommodations
  • Cabins: 21 self catering accommodations
  • Bungalows: 21 self catering accommodations

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

Can I find a holiday accommodation with pool in Chester?

Yes, you can select your preferred holiday accommodation with pool among our 46 holiday homes with pool available in Chester. Please use our search bar to access the selection of holiday rentals available.

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