Chestertown Vacation Rentals: condo and apartment rentals & more

Discover a selection of 83 vacation rentals in Chestertown that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $111 per night, and condos and houses are popular options for a stay in Chestertown. Either way, you'll find a rental for everyone's needs.

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Find the best place to stay — Chestertown

Search 83 vacation rentals

Stayed Apr 2021

Beautiful property

The house is right on the river, with a dock just off the back yard. The sandy beach on the property was a hit with the kid. The owners are very helpful and communicative, and live right next door. We had access to kayaks and paddle boards and enjoye...

Stayed Apr 2021

Fabulous cottage

We loved our stay here- the cottage was pristine, beautifully decorated and well stocked. We divided our time between exploring historic Chestertown (lovely) and relaxing in the cottage’s comfortable living room. The host was very responsive and kind...

Stayed Apr 2021

Amazing location for a getaway!

This property and location was the perfect getaway from the city. The house had everything we needed to work remotely and to enjoy the area. It's a quick drive to the town and shops, but the privacy of the large lot made for a great escape. The water...

Stayed Apr 2021

This has become a destination...

Though we, originally, stayed here as we passed through to another destination this home and it’s hosts have turned it into a destination for us. With its proximity to both the city and beach, while remaining uniquely itself, we cannot wait to visits...

Stayed Apr 2021

A beautiful house in a relaxing setting

What a beautiful place to get away from it all. There were so many ways to enjoy all of the beauty and peace the area has to offer. There is so much outdoor room – a dock, a deck, a screened-in porch to listen to the sounds of birds and wind in the t...

Stayed Apr 2021

Perfect getaway with young kids

We literally just left, and my kids are already asking when we can go back to the llama farm with the little beach and the boats. We had a wonderful stay at this gorgeous property, and the hosts were perfectly helpful and accommodating. This is a cot...

Stayed Apr 2021

The Lighthouse Exceeded Our Expectations!

My husband, our tween daughter and I thoroughly enjoyed our stay at the lighthouse. The home was so special and unique. As far as cleanliness goes, the home was immaculate. Considering the current environment that made us feel very safe. The Lighthou...

Stayed Apr 2021

Great Stay

We did a short family getaway to this house; as described in the other reviews the backyard and views are simply amazing. The entire property is very peaceful with just the sounds of nature. The dock and the pier were amazing to just hang out and rea...

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Destination guide

The cozy city of Chestertown awaits you

Enjoy the area's festivals, history and art galleries and make a vacation rental your home during your stay in Chestertown. This city's sporting events, university setting and boating draw many visitors. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities

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 cozy vacation rental and check out everything that Chestertown has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

Cassinelli Winery and Vineyards (7.1 mi / 11.5 km)
Tilmon's Island Winery (12.4 mi / 20 km)
Queenstown Harbor Golf Club (15.4 mi / 24.8 km)
Rocky Point Golf Course (17.4 mi / 28.1 km)

Natural features

Exploring the natural landscape of Chestertown

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Chestertown. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

Wilmer Park (1.4 mi / 2.3 km)
Ferry Park (9.9 mi / 15.9 km)
Adkins Arboretum (19.4 mi / 31.2 km)
Elk Neck State Park (19.8 mi / 31.9 km)
Sandy Point State Park (21.1 mi / 33.9 km)
Kent Island (21.6 mi / 34.8 km)

How to get there

Transportation to and around Chestertown

The nearest airport is in Baltimore, MD (MTN-Martin State), located 19.5 mi (31.4 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Easton, MD (ESN-Easton - Newnam), which is 27.3 mi (43.9 km) away.

How many vacation rentals are available around Chestertown?

Our 2021 property listings offer a large selection of 83 vacation rentals around Chestertown. From 7 condo and apartment rentals to 71 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.