Chestertown Vacation Rentals

Welcome to Chestertown. Scroll down this page to find your favorite travel destination in Chestertown and browse our extensve inventory of accommodations in Chestertown. Leisure travelers planning their family vacations can get offers directly from owners of Chestertown vacation homes or houses in Chestertown. Sometimes these single rental units are referred to as Chestertown cabins or Chestertown villas. Other popular lodging options include vacation rentals in Chestertown, Chestertown apartments and condos in Chestertown. For business travelers we offer several convenient hotels in Chestertown or small boutique hotels in Chestertown area, many with the ability to book online. If you are planning a romantic getaway in Chestertown, we highy recommend our unique inventory of bed and breakfasts in Chestertown. B&Bs can also referred as small country inns in Chestertown.

Finding the perfect vacation rental property can be very time consuming. Unlike many other sites out there that demand travelers (like you) to invest countless hours browsing though each vacation rental listing, at we make it easy for travelers to find best Chestertown vacation rentals using our free inquiry service or Chestertown lodging locator service. Save time searching for Chestertown rental vacations and Chestertown accommodations! Simply click the "Inquire Now" button, complete a short inquiry form, and within minutes you will start receiving multiple offers from Chestertown vacation home rentals owners as well as from Chestertown resorts, Chestertown cabin rentals, and Chestertown vacation homes.

Let Rentalo help you find the perfect place to stay for your next family vacation in Maryland area. Our engine will match your specific inquiry criteria with each Chestertown vacation rental listing, Chestertown vacation house or Chestertown villa in our Chestertown rental vacations inventory. Finding Chestertown vacation rentals by owner is easy with our free inquiry service. However, you can also browse our inventory of Chestertown accommodation listings (as listed below) or use the SmartSearch tool to narrow down your search for Chestertown lodging in Maryland.

Enter your travel dates and number of people traveling (sleeps) and use one of the following search options:

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  3. Inquire only on a Specific Chestertown Vacation Rental (Take the time to review each property - Receive an offer on the Property you like)
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ID: 64648
Comfort Suites Chestertown - Hotel in Chestertown
53 Bedrooms
Location. The comfort suites chestertown is located in chestertown, md. one-and-one-half miles from kent county historical society two miles from kingstown park hotel features. complimentary high-spee ...Read Full Description
ID: 386537
Elizabeth's Elegant Guest House in Chestertown - Hotel in Chestertown
6 Bedrooms
Sleeps 20
This beautiful house is one of the largest vacation rentals in the entire adirondack region. It can sleep 20 people. the house is conveniently located in the quaint village of chestertown. walk to fin ...Read Full Description
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Smart Search

*Traveling Dates:

Flexible Dates
1+ (2)
3+ (2)
6+ (2)
11+ (2)

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4+ (2)

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Hotels (2)

Cable/Satellite TV (1)
High Speed Internet (1)

Special Features:
Children Welcome (2)
Smoking Permitted (2)
Pet friendly (1)
Handicap accesibility (1)

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Cambridge (4)

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