61+ Vacation Rentals & Holiday Homes in Chestertown |
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Chestertown Accommodations - Hotels & Rentals

About Chestertown Vacation Rentals

Discover More than 61 Incredible Getaway Rentals Available in Chestertown. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Chestertown.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Chestertown, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Chestertown. The Average Size of Places to Stay Near Chestertown is 868.02 ft², with Prices Averaging US $515 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Chestertown. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Chestertown

Type Count
Vacation Homes 39
Holiday Apartments 9
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Chestertown

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Chestertown with Online Reservations.

Weather in Chestertown, MD

View the weather forecast for Chestertown before booking your Chestertown Vacation Rentals to confirm your best time to go.

December - February
High 56°F       Low 33°F
March - May
High 73°F       Low 38°F
June - August
High 90°F       Low 69°F
September - November
High 80°F       Low 42°F

Activities ChestertownGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World ChestertownGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Washington College
Wilmer Park
Rolphs Wharf Marina
Historical Society of Kent County Maryland
River Arts Chestertown
Garfield Center for the Arts at the Prince Theater
U.S. Naval Academy
Ripken Stadium
White Marsh Mall
Chesapeake Bay Bridge
Fort McHenry
Sandy Point State Park
Canton Waterfront Park
Queenstown Premium Outlets
Annapolis Maritime Museum
Queenstown Harbor Golf Club
Liriodendron Mansion
Havre de Grace Promenade
Bay Hills Golf Club
Maryland World War II Memorial

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Great Oak Landing 147 Properties
Kent County 137 Properties
Georgetown 137 Properties
Tolchester Beach 66 Properties
Pomona 48 Properties
Fairlee 43 Properties
Wilmer Park 40 Properties
River Arts Chestertown 40 Properties
Garfield Center for the Arts at the Prince Theater 40 Properties
Historical Society of Kent County Maryland 40 Properties
Washington College 40 Properties
Rolphs Wharf Marina 27 Properties

Frequently Asked Questions About Chestertown?

What are the top hotels, lake houses & vacation rentals in Chestertown?

We provide an array of great vacation destinations in Chestertown. If you are looking to stay in or around the Chestertown area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Chestertown:

Which hotel, lake house, or vacation rental in Chestertown is best for families?

Searching for a family-friendly getaway in Chestertown? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Chestertown?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 61 in the Chestertown area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Chestertown.


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