Discover a selection of 40 vacation rentals in Chestertown, MD 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 $125 per night, and houses and condos are popular options for a stay in Chestertown. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Chestertown
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Destination guide

Why people love visiting cozy Chestertown

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.

Things to do

Activities and attractions in Chestertown

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:

  • Queenstown Harbor Golf Club (16.7 mi / 26.9 km)
  • Queenstown Harbor Golf Links (16.7 mi / 26.9 km)
  • Compass Pointe Golf Courses (23.8 mi / 38.2 km)
  • Cassinelli Winery and Vineyards (7.1 mi / 11.3 km)
  • Crumpton Auction (8.4 mi / 13.5 km)
  • Crow Farm and Vineyard (10.2 mi / 16.4 km)
Natural features

Exploring the natural landscape of Chestertown

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:

  • Betterton Beach (10.5 mi / 16.9 km)
  • Gunpowder Falls State Park (17.9 mi / 28.9 km)
  • Elk Neck State Park (18.6 mi / 29.9 km)
  • Chesapeake Bay Environmental Center (20.6 mi / 33.1 km)
  • Sandy Point Beach (22.6 mi / 36.4 km)
  • Sandy Point State Park (22.7 mi / 36.5 km)
How to get there

Transportation options to and around Chestertown

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.

What are the top vacation rentals in or near Chestertown?

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:

  • Around 7 miles from the center of Chestertown, you'll love staying at "Water Front Retreat - Sunrise And Sunset Water Views". It has 3 bedrooms and a range of conveniences like a bicycle and a hair dryer.
  • Another top choice is "Historic Downtown Chestertown Home. #1 Location", which is around 1 mile from Chestertown. With 2 bedrooms, WiFi and a fenced yard, it has everything you need to keep you comfortable and happy.

For even more great options, use the search bar at the top of the page to find the perfect Chestertown vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Chestertown?

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:

  • Find some peace at "Historic Stepne Manor On Maryland's Eastern Shore". Located around 1 mile to the east of Chestertown, this cozy escape has everything you need for a relaxed stay, including a boat and free toiletries.
  • Alternatively, create new memories with your loved ones at "Country Estate In Historic District", which is around 1 mile to the east of Chestertown. You'll have use of a porch, a fireplace and more here.

Can I find studio apartments for rent in and around Chestertown?

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:

  • One of our top picks is "Eastern Shore Get Away". Lock in a few nights at this popular apartment and you'll have access to a restaurant dining guide and nearby hunting activities.
  • "First Floor Studio Apartment In Historic Chestertown" is another top stay, providing all you could want for a great Chestertown vacation. Handy amenities here include spa and beauty services and nearby museums.

Can I find short term rentals in or near Chestertown?

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:

  • If you only need to stay a few nights, "Hidden Gem With Water And Golf Course Views Bike Ride To Downtown" is a good choice. It's close to central Chestertown, so you'll have easy access to all the top sights.
  • Another terrific option is "Circa 1900 Home In The Heart Of Historic Downtown Chestertown". Round up your favorite people and enjoy a comfy stay close to the heart of Chestertown.

What are the best romantic weekend getaways in or near 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:

  • Put on some mellow music and chill together at "Water Front Retreat - Sunrise And Sunset Water Views". Around 7 miles from Chestertown, this property has all you need for a romantic weekend getaway, including beauty services and a fireplace.
  • Otherwise, spend a few days sipping on bubbly and canoodling at "Historic Downtown Chestertown Home. #1 Location", around 1 mile from Chestertown. A nearby bay and beauty services will help ramp up the romance.

What are the best large group vacation rentals in or near Chestertown?

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:

  • A great range of amenities including a garden and a kitchen make "Historic Stepne Manor On Maryland's Eastern Shore" a top pick. This spacious property has 5 bedrooms and accommodates up to 15 guests. From central Chestertown, it's around 1 mile away to the east.
  • Nothing's more important than spending time with the people you love, and "Country Estate In Historic District" is the ideal place to do that. Located around 1 mile to the east of Chestertown, as many as 12 people can stay in this vacation rental which has 5 bedrooms. A garden and a kitchen are among the many amenities on offer here.

What are the best houses for rent with a pool in or near Chestertown?

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:

  • Pack your swim gear and make a booking at "Rambling Victorian Beach House On Maryland's Eastern Shore". There are also lots of other appealing amenities here, including a smart TV and a fridge.
  • Alternatively, unpack your bags at "Carriage House Hideaway In Middle Of Chestertown". As well as its inviting pool, you'll also have use of a travel crib and coffee and tea making facilities.

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.

What are the best large family vacation rentals in or near Chestertown?

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:

  • Located approximately 7 miles to the south of Chestertown, "Water Front Retreat - Sunrise And Sunset Water Views" fits up to 8 people over 3 bedrooms. As well as tons of space to sprawl out, amenities here include a garden and on-site watersports.
  • Another home away from home is "Historic Stepne Manor On Maryland's Eastern Shore". Around 1 mile east of Chestertown, it comes with 5 bedrooms, room for up to 15 guests, outdoor furniture and a fridge.

Can I find two-bedroom vacation rentals in or near Chestertown?

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:

  • "Holiday Apartment Dramalj For 2" is a perfect choice for small groups and families. As well as two bedrooms, this relaxing stay offers amenities like a swimming pool and a garden.
  • Another highly recommended option is "Chestertown's Pet - Friendly Little Red Cottage". With useful amenities like a kitchen and a firepit, you'll have no trouble making yourselves at home here. Choose your favorite room, unpack your suitcases and let the party begin!

What are the best three-bedroom vacation rentals in or near Chestertown?

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:

  • Book a few nights at "Hidden Gem With Water And Golf Course Views Bike Ride To Downtown". With amenities such as a firepit and a kitchen, this roomy stay will have you all feeling right at home.
  • Another superb three-bedroom rental is "Private Waterfront Paradise With Pier". Take advantage of a nearby waterfront and a fireplace while spending quality time with the people close to you.