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  4. Oceanfront Vacation Rentals

Chestertown Oceanfront Vacation Rentals & Beachfront Homes

Book places to stay in Chestertown for your next beach vacation

About Chestertown Oceanfront Vacation Rentals on Rent By Owner

With more than 18 oceanfront rentals in or near Chestertown, Rent By Owner features many wonderful beachfront places to stay. Are you traveling with groups, families, friends, or as a couple to Chestertown? RBO vacation homes will give you maximum comfort and essential amenities such as full kitchens, Wi-Fi, hot tubs, outdoor pools, recreation and theater rooms, laundry facilities, and more for your comfort.

Looking for a beach or oceanfront rental in Chestertown, Maryland with a pool? Rent By Owner has a large selection of villas, condos, cabins, and cottages. There are rentals for both large and small travel groups. RBO vacation homes can assist you in finding the perfect accommodation in Chestertown that meets your travel budget, giving you the option to find direct access to the stunning beaches and ocean views, Rent by Owner has plenty of room for an extended family or small family, whether you are looking for a luxury villa, resort, furnished home, cozy condo with breathtaking views with private bedrooms and baths near Chestertown, find an oceanfront rental with an amazing view.

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Frequently Asked Questions About Chestertown Oceanfront Rentals

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 Oceanfront Vacation Rentals in Chestertown:

The average price per night for an ocean-view holiday rental in Chestertown is $527. Check the list of beach view accommodations in Chestertown.
There are 18 ocean views rental properties that are available to rent. You can book for your next trip with Rent By Owner.
Yes, here are some popular beachfront vacation rentals in Chestertown that have a private or heated pool:Check all holiday rentals with a pool in Chestertown on Rent By Owner.
Yes, we have Chestertown ocean view rentals in Chestertown that are pet-friendly, some of these pet-friendly places to stay in Chestertown include:
  • Vacation Homes: 18 available for rent
  • Villas: 18 Rental available for rent
  • Holiday Apartments: 18 rentals available for rent
  • Hotels with Suites: 18 rentals available for book