Photo by Patricia Knorr

Chester vacation rentals

We found 196 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 8 homes and other vacation rentals in Chester that are perfect for your trip. Vacation rentals offer the best amenities for your family, friends, or furry companion, such as WiFi and a hot tub. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

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Explore the waterfront setting in Chester

The island views and other outdoor surroundings create an inviting atmosphere in Chester. Renowned for its boating, biking and seafood restaurants, this city welcomes all visitors. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Chester

Are you hoping to find things to do in the area? Venture out of your vacation home and check out everything that makes Chester a one-of-a-kind vacation spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Queenstown Harbor Golf Club (6.5 mi / 10.5 km)
  • St. Michaels Winery (13.9 mi / 22.4 km)
  • Paul Reed Smith Guitars (1.6 mi / 2.6 km)
  • Queenstown Harbor Golf Links (6.6 mi / 10.5 km)
  • U.S. Naval Academy Golf Club (9.5 mi / 15.3 km)
  • Thurgood Marshall Memorial (10.9 mi / 17.5 km)

Exploring the natural landscape of Chester

Whether you're an active traveler or just want to spend some time taking in the scenery, Chester is a great place to get outside. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Chesapeake Bay Environmental Center (3.8 mi / 6.1 km)
  • Love Point State Park (4 mi / 6.5 km)
  • Sandy Point Beach (6.2 mi / 10 km)
  • Sandy Point State Park (7 mi / 11.3 km)
  • Maryland Quiet Waters Park (11.4 mi / 18.3 km)
  • Matapeake State Park (3.6 mi / 5.8 km)

Traveling to and around Chester

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 16.6 mi (26.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Baltimore Washington Intl. Airport (BWI), which is 24.8 mi (39.9 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chester?

The most in-demand types of vacation rentals in Chester are houses. Prefer something different? Vrbo has a variety of options to match the unique needs of our guests, so you'll see vacation homes in all sizes and shapes. The perfect home away from home is waiting for you — discover yours today.

How much does it cost to rent a vacation rental in Chester?

Several factors affect how much you pay for a vacation rental in Chester, such as the type of property, season and length of stay. But, all Vrbo homes have one thing in common — unbeatable value. Just add your travel dates to find your ideal match.

How much does it cost to rent a beach house in Chester?

The average price for a vacation rental close to the beach in Chester depends on when you're traveling and the type and size of property you want. You can easily find prices on Vrbo by entering your destination and preferred travel dates. Then make use of the filter tool to pick the number of bedrooms and amenities that you prefer, like a pool, air conditioning and WiFi.

Are there pet-friendly vacation rentals in Chester?

Pack up a suitcase for your puppy dog because Chester has five vacation homes that throw out the welcome mat to pets. Let your furriest pal get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check the "Pets allowed" filter box.

Can I rent a house with a pool in Chester?

Pack your swimming gear and inflatable flamingo, because there are two houses with a private pool in Chester. Stay at one of these superb vacation homes and enjoy a pool day every day. Simply enter your dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!

What are popular rental amenities in Chester?

The most popular rental amenities people look for in Chester include a garden, nearby museums and a fireplace. Whether you're on a trip with family, pals or even pets, Vrbo vacation rentals provide the best amenities for chilling out with the people who matter most.

Are there large group vacation rentals in Chester?

Choose from two vacation rentals in Chester that can host 10 or more guests. Whether you're organizing a family trip or a celebration like an anniversary, there's plenty of room to get your loved ones together under one roof.

Are there vacation rentals in Chester that welcome kids?

Chester has five family-friendly vacation homes to pick from. And finding a stay that welcomes kids is a cinch with Vrbo's "Properties good for families" filter. In addition to having the entire place to yourselves, you'll have access to conveniences and perks like extra bedrooms, kitchens and yards.

What are the top attractions for families in Chester?

Keeping the kids entertained during your stay in Chester is simple with these cool family-friendly attractions:

  • Sandy Point Beach
  • Bay Ridge Beach
  • Sandy Point State Park

Are there vacation rentals with WiFi in Chester?

Take your pick of two vacation rentals with WiFi in Chester. If you'd like to disconnect from the world while on vacation, but still want to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Chester?

Chester has four vacation rentals where you'll be able to kick back in air-conditioned comfort. To find a stay on Vrbo that features this perk, enter your preferred travel dates and use the handy filter tool to select the "air conditioning" box.

How old do you have to be to rent a vacation rental in Chester?

The minimum age is generally 16, 18 or 21. It can vary between properties on Vrbo, so look at the rules of your chosen Chester stay before booking your stay.

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