62+ Rental Villas and Private Getaways in Chestertown |
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Chestertown Villa Rentals

About Chestertown Vacation Rentals

There are more than 62 incredible getaway rentals that are available in Chestertown. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Chestertown.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Chestertown, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Chestertown. Places to stay near Chestertown are 950.86 ft² on average, with prices averaging GB £396 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Chestertown. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Private Villas, Resorts, and Rentals in Chestertown

Type Count
Vacation Homes 40
Holiday Apartments 9
Cottages 3
Cabin Rentals 2
Others 2
B&B 1

Use these Quick Filters to Find a Vacation Rental in Chestertown

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Chestertown with BedroomVillas.

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

Stay Near Chestertown's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Chestertown's Research Top Attractions For Your Vacation


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, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Great Oak Landing 147 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
Kent County 30 Properties
Rolphs Wharf Marina 27 Properties

Frequently Asked Questions About Chestertown?

What are the top hotels or resorts 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 or resort 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?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 62 in the Chestertown area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Chestertown. 


People Also Ask

There are 5 hotels in Chestertown and 51 rentals

Recently Booked Hotels, Resorts, or Rentals in Chestertown