Discover a selection of 142 holiday rentals in Chester 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 £ 91 per night, and houses and cottages are popular options for a stay in Chester. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chester
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.

Can I find a vacation rental around Chester?

Yes, our 2021 property listings offer a large selection of 142 vacation rentals near Chester. From 125 houses to 19 cottages, 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.