Photo by Patricia Knorr

Chester holiday lettings

We found 194 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 9 homes and other holiday rentals in Chester that are perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Explore the waterfront setting in Chester

The island views and other outdoor surroundings create an inviting atmosphere in Chester. Renowned for its boating, cycling and seafood restaurants, this city welcomes all visitors. With a holiday 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 discover top things to see and do while you're in town? Venture out of your cosy holiday rental and check out everything that makes Chester a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Queenstown Harbor Golf Club (6.5 mi / 10.5 km)
  • St. Michaels Winery (13.9 mi / 22.4 km)
  • Queenstown Harbor Golf Links (6.6 mi / 10.5 km)
  • U.S. Naval Academy Golf Club (9.5 mi / 15.3 km)
  • Maryland World War II Memorial (10.4 mi / 16.8 km)
  • Thurgood Marshall Memorial (10.9 mi / 17.5 km)

Exploring the natural landscape of Chester

Whether you're an active traveller or just want to take in the scenery, Chester is a great spot to appreciate mother nature. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Patapsco River (26.1 mi / 42 km)

Travelling to and around Chester

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 16.6 mi (26.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Baltimore Washington International Airport (BWI), which is 24.8 mi (39.9 km) away.

Frequently asked questions

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

The most in-demand types of holiday 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 holiday 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 holiday rental in Chester?

Several factors affect how much you pay for a holiday 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 holiday rental close to the beach in Chester depends on when you're travelling 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 holiday rentals in Chester?

Pack up a suitcase for your puppy dog because Chester has five holiday 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 holiday 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 holiday 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 holiday rentals provide the best amenities for chilling out with the people who matter most.

Are there large group holiday rentals in Chester?

Choose from two holiday rentals in Chester that can host 10 or more guests. Whether you're organising 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 holiday rentals in Chester that welcome kids?

Chester has five family-friendly holiday 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 holiday rentals with WiFi in Chester?

Take your pick of two holiday rentals with WiFi in Chester. If you'd like to disconnect from the world while on holiday, 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 holiday rentals with air conditioning in Chester?

Chester has four holiday 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 holiday 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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