Take a vacation 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 vacation rentals feature full kitchens and laundry facilities.
Do you want to find top things to see and do while you're in the area? Venture out of your vacation home and experience everything that makes Chestertown a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:
Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Chestertown is a great place to spend some time outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city center:
The nearest airport is in Baltimore Washington Intl. Airport (BWI), located 32.2 mi (51.9 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Baltimore, MD (MTN-Martin State), which is 20.3 mi (32.7 km) away.
Whether you're seeking an intimate retreat for you and your honey or somewhere spacious to fit all your friends, you'll find some top vacation rentals in and around Chestertown. Here are a couple to get you inspired:
For even more great options, use the search bar at the top of the page to find the perfect Chestertown vacation rental for you.
Get away from the daily grind at one of our weekend getaways in or near Chestertown. Whether you want to catch up with pals or spend quality time with your love, there'll be something to suit your style. Here are some of our most popular options:
Studio apartments are a simple yet stylish choice, ideally suited for couples or solo adventurers. Spend your days familiarizing yourself with your new surroundings and your nights resting up in your cozy hideaway. These getaways in or near Chestertown are sure to please:
From modern apartments to huge vacation homes, Vrbo has your mini vacation sorted. Here are some of our most popular stays in and around Chestertown:
Forget chocolates and roses. Sometimes all you need is to get away for a weekend, just you and your sweetheart. At Vrbo, we've got romantic getaways in and around Chestertown that would make even Cupid swoon. Here are some we think you'll love:
Big groups mean massive fun. They also mean finding a place that'll comfortably fit your crew. Browse our large group vacation rentals in or around Chestertown and get your loved ones together under the same roof:
Nothing screams fun like a pool. Pull out your flamingo floatie and check out these rental houses in or near Chestertown that come with this must-have amenity:
Chestertown has a humid subtropical climate, with average summertime temperatures hovering between 70 ºF and 80 ºF. But there's no need to wait until summertime to visit. Check out the search bar at the top of the page and adjust the filters to find the ideal Chestertown vacation rental and organize your getaway for whatever season you like.
Comfort, space and privacy are key to any great family getaway, and Vrbo's range of large family vacation rentals in and around Chestertown offer the ideal solution. Here are a few to get you started:
At Vrbo, we've got vacation rentals in or near Chestertown to suit all styles and budgets. Here are a couple of two-bedroom options to consider:
Three-bedroom rentals in or near Chestertown give you both freedom and space to enjoy your vacation with family and friends. Take a peek at some of the options available here: