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Chestertown Maryland USA Vacation Rentals by Owner

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Overview of Chestertown Vacation Rentals

Explore Historic Kent County from Your Own Chestertown Vacation Rentals

Chesterton is a charming colonial town on the banks of the Chester River and the important seat of Kent County. With its maritime history, cultural attractions, scenic countryside, excellent shopping and dining, it is a popular vacation destination on Maryland's Upper East Shore. The river is lined with mansions built by wealthy merchants in the 18th century. The county courthouse and impressive churches make this a memorable place to explore from your Chestertown vacation home.

There Are a Host of Things to Do Around Chestertown Vacation Houses

Chestertown is surrounded by farmland and has many estuaries into the lovely Chesapeake Bay, offering plenty of activities for outdoor enthusiasts. Rent kayaks or take a boat trip to see herons, ospreys, eagles and other wildlife along the river. Driving tours are popular in the area, along with bike rides and self-guided tours of the historic district. Just pick up directions from the local visitor center to make the most of this lovely area.

Visitors can also see Washington College, founded by George Washington himself with his donation of 50 guineas. The area is rightly proud of its history and celebrates with a number of festivals, including a Tall Ship Festival, Downrigging Festival, a historic Tea Party Festival and Wild Fowl Festival.

The replica of the historic Schooner Sultana is moored on the Chester River and offers a taste of the area's maritime past, which dates back to 1640. The farmers' market and the artisans' ,arket on Park Row are in the heart of downtown and sell everything from freshly baked bread to works of art each Saturday. Stroll the waterfront and admire the grand houses or enjoy the many galleries and art studios and buy an appropriate souvenir of your stay in Chesterton.

The Seasons and Weather at Your Chestertown Lodging

Chesterton has plenty of sunshine resulting in hot summer days averaging 90 F (32 C). The winter months are generally below freezing. The area has around four inches of precipitation each month and around six inches of snowfall from December through March. Spring and fall are particularly lovely times to visit Chesterton.

Maryland Vacation Rentals Are Easy to Reach

Your Chestertown vacation rental is about 32 miles from the Baltimore-Washington (BWI) International Airport, making it very easy to get to from all over the United States and further afield. A car rental is useful for reaching Chesterton and for exploring the area during your stay.

What Guests Love About Chestertown Lodging

Most visitors to Chesterton prefer to stay in a vacation rental home for the freedom and flexibility they offer. Well located, they have all you need for a relaxing vacation with plenty of space for families large and small. Bring the in-laws, family, friends and even the pet dog. Sharing the costs makes this a very economical way to enjoy a vacation without sacrificing standards. The fully equipped kitchens are ideal for preparing breakfasts and packed lunches, helping to save money on expensive meals out.

Top Places to Visit from Maryland Vacation Rentals in Chesterton

Betterton Beach makes a great day out for families, just 15 miles from your Chestertown lodging. Located on the estuary of the Sassafras River, it has a fishing jetty, swimming area, beach, picnic pavilion and bath house. The Eastern Neck National Wildlife Refuge is 20 miles south of Chesterton and offers a quiet place for enjoying the wildlife of the area. The Geddes-Piper House Museum in Chesterton, built for the local Customs Inspector in 1784, is also well worth a visit; it is managed by the Historical Society of Kent County. The nearby town of Rock Hall on the bay front has many marinas and work boats to see. You could also head for the quaint town of Galena, known for its antique shops.

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