Ready for a sun-soaked trip to Chestertown? Explore our index of beach house rentals and sunny coastal apartments. Owner Direct helps you filter through verified seaside options to find your next relaxing shore retreat.
Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Family
Fabulous
5 reviews
Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio
Exceptional
31 reviews
Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals
Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Living Area, Microwave
Review score
4 reviews
View, Parking, Air Conditioner, Internet, Private Beach, Ocean View, Child Friendly
Superb
3 reviews
AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet
Exceptional
16 reviews
Apartments, Cheap, Accommodations, Lodgings, Beach, Places to stay, Ski resorts
Superb
8 reviews
AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
13 reviews
Apartments, Accommodations, Lodgings, Beach, Places to stay, Ski resorts, Condos
Review score
7 reviews
Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space
Fabulous
36 reviews
Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen
Exceptional
5 reviews
Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Jacuzzis
Exceptional
3 reviews
AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen
Very Good
47 reviews
Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals
AC, Arcade, Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen
Exceptional
7 reviews
Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals
Very Good
3 reviews
AC, Arcade, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area
Exceptional
22 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry
Exceptional
23 reviews
AC, Arcade, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave
Fabulous
8 reviews
AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet
Exceptional
36 reviews
Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Beach Rentals in Chestertown.
OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
What makes our beach rentals stand out?
Every beach rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Compare a range of properties and find fair, transparent pricing—no hidden fees.
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Some of the best beach rentals in Chestertown are:
There are a lot of options in Chestertown. If you plan on staying in the Chestertown area, consider making a reservation for a few nights at one of these properties as these have been rated the top Beach Rentals in Chestertown
You can explore 56 verified beach rentals in Chestertown. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.
Beach rental prices in Chestertown vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $165 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.
Many beach rentals in Chestertown offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.
Yes, many beach rentals in Chestertown welcome pets. Currently, 16 listings allow pets, although policies may vary by property. It's also a good idea to check local beach regulations for any restrictions on pets during your stay.
For peak travel periods such as summer holidays or spring break, it's recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.
Beach rentals in Chestertown often include amenities designed for coastal living, such as View, Ocean View, and Fireplace/Heating. These features help enhance comfort and make it easier to enjoy time by the water.
Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It's best to review the amenities section of each listing to confirm what is included and plan accordingly.