Photo by Assya A

Chestertown holiday homes

We found 59 holiday rentals — enter your dates for availability

Discover a selection of 24 homes and other holiday rentals in Chestertown that are perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, including parking and a garden. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Why people love visiting cosy Chestertown

Take a holiday to Chestertown and enjoy the area's festivals, history and art galleries. This city's sporting events, university setting and boating draw many visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Chestertown

Do you want to discover top things to see and do while you're in town? Venture out of your cosy holiday rental and experience everything that makes Chestertown a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Queenstown Harbor Golf Club (16.7 mi / 26.9 km)
  • Queenstown Harbor Golf Links (16.7 mi / 26.9 km)
  • Paul Reed Smith Guitars (20.7 mi / 33.3 km)
  • Compass Pointe Golf Courses (23.8 mi / 38.2 km)
  • Bay Hills Golf Club (25 mi / 40.2 km)
  • Cassinelli Winery and Vineyards (7.1 mi / 11.3 km)

Exploring the natural landscape of Chestertown

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Chestertown is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Betterton Beach (10.5 mi / 16.9 km)
  • Ferry Park (11.5 mi / 18.5 km)
  • Eastern Neck National Wildlife Refuge (15.4 mi / 24.8 km)
  • Miami Beach (17.2 mi / 27.7 km)
  • Rocky Point Park and Beach (18.1 mi / 29.2 km)
  • Chesapeake Bay Environmental Center (20.6 mi / 33.1 km)

Transport options to and around Chestertown

The nearest airport is in Baltimore, MD (MTN-Martin State), located 20.3 mi (32.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away.

Frequently asked questions

What is the best area to stay in Chestertown when booking a holiday home?
Among the more sought-after neighbourhoods to find a Chestertown holiday home is Fairlee. When you lock in your Bookabach holiday property, you will have the whole place to yourself. So you won’t have to share it with anybody except for your favourite people.
What is the most popular type of holiday home accommodation in Chestertown?
Houses are the most popular style of holiday home in Chestertown, according to our data. Even if you’ve got something different in mind, Bookabach has properties in all shapes and sizes. Take a look at our options to find your ideal fit.
How much does it cost to rent a holiday home in Chestertown?
A number of factors affect what you’ll pay for your holiday home in Chestertown, such as the season, length of stay and type of property. But, all our holiday homes have something in common — excellent value. Just enter your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Chestertown?
When you travel and the size and style of the property will influence how much you’ll pay for your beachside escape. Put in your Chestertown travel dates to see all your options on Bookabach. Looking for basics like WiFi, or perks like a private pool? Use the filters to choose the features and amenities you want in your home.
Are there pet-friendly holiday homes in Chestertown?
You’re in luck! There are. You can pick from 13 holiday homes that cater to pets in Chestertown. Many of our pet-friendly holiday homes come with an outdoor space for your furry friend to play in, complimentary treats, special dog beds and proximity to parks and green space. Apply the “Pets allowed” filter to find a pad that’ll get tails wagging on Bookabach.
Can I rent a house with a pool in Chestertown?
Dig out your swimsuit and swim ring, because there are two houses with a private pool in Chestertown. Make a booking at one of these superb holiday homes and every day will be a pool day. Simply enter your travel dates into Bookabach, then check the “pool” filter to find a place to make a splash!
What are popular home amenities in Chestertown?
A nearby river, a garden and a firepit top the list of most popular home amenities in Chestertown. Whether you’re travelling on your own, with your other half or a group of dear friends, Bookabach will help you find a holiday home that fits your tastes with all the features you’re looking for.
Are there large group holiday homes in Chestertown?
With three properties that can sleep 10 or more people in Chestertown, you don’t have to keep anyone off the invite list. From holidays with the extended family to special events like birthday and Christmas parties, Bookabach can help you find a large group home to suit the occasion.
Are there holiday homes in Chestertown that welcome kids?
Gather your whole family for an unforgettable adventure in Chestertown at one of our 13 family-friendly holiday homes. Many of these stays feature conveniences that are suitable for getaways with the little ones, like full kitchens, living rooms and pools. Just click on the “Properties good for families” filter and select your favourite.
What are the top attractions for families in Chestertown?
Keep the kids entertained at these leading family-friendly attractions in Chestertown:

  • Historical Society of Kent County Maryland
  • River Arts Chestertown
  • Rolphs Wharf Marina

Can I find two-bedroom holiday homes in Chestertown?
You can pick from four two-bedroom homes in Chestertown. Put the kids in the second room or maybe fill it with a couple of your best friends. There’s ample space for whoever’s lucky enough to be coming along.
Are there holiday homes with WiFi in Chestertown?
You can choose from eight holiday homes with WiFi in Chestertown. If you want to disconnect from daily life on your escape, but still need to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Chestertown?
Choose from 13 Bookabach holiday homes with air conditioning in Chestertown giving you that cool, cool breeze and extra element of comfort. Just enter your preferred travel dates and then make use of our filters to locate stays with air conditioning.
How old do you have to be to rent a holiday home in Chestertown?
The minimum age allowed can differ between properties on Bookabach, so look at the rules of the holiday home in Chestertown you’re interested in. But in general, it’s 16, 18 or 21.
How long can I rent a holiday home in Chestertown for?
It’s up to the Chestertown property. To look over a list of options offering extended stays, just enter your dates and guest number into Bookabach. Look forward to having the entire property to yourself, along with comforts such as air conditioning, a kitchen and a yard where the little ones can play. Keep an eye out for long-term stays that offer weekly or monthly discounts.

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