Chestertown Vacation Homes

Vacation homes offer you holiday time with flexibility.

With your own vacation home you avoid the uncertainty of hired accommodation. Vacation homes can be jointly owned, or wholly owned, and allow you to spend time regularly in your favourite vacation area. Vacation homes can be more or less self-funding, as you can rent yours out to tourists when you aren’t using it. Vacation home lets are really made easy with the Internet, with many agents specialising in this market. Vacation home swaps allow you to stay in new destinations too, if you own a vacation home.

Vacation homes are cheaper to rent than hotel accommodation, especially for families. Whatever your interest, as buyer or tenant, call around and look online into the options for vacation homes.

Vacation Homes in Chestertown, Maryland, United States

  • Chestertown Historic House

    Chestertown Historic House offers fine antique furnishings and paintings in keeping with the history of this wonderful home. Enjoy watching the world go by from the porch in the heart of beautiful Chestertown, Maryland, and distant views of the Chester River. This circa 1780 and 1840 house provides a wonderful level of comfort in the master bedroom with his and hers bathrooms, two more bedrooms with private baths, a gourmet kitchen, controlled heating, air conditioning and so much more. Chestertown Historic House also has an outside grill, and is a simply wonderful place to stay as a self catering option when visiting Chestertown, Maryland.


  • Banning House

    Banning House in Chestertown, Maryland is a beautifully restored family home perfect for self catering holidays just up from the Chester River. Enjoy a vacation rental that is within walking distance from everything, has a wonderful porch from which to watch the world go by, and an outdoor patio with grill. Banning House is located in the heart of the historic district of Chestertown, where guests can enjoy a stay in the spacious bedrooms with queen beds, a contemporary kitchen that is fully equipped, a sun room and dining room. A stay in this historic house originally built in 1785, offers perfect surrounds in a lovingly restored home.


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