Chestertown Summer Rentals, Cottages & Cabins

Book a Place to Stay in Chestertown for Your Summer Getaway

About Chestertown Summer Rental on Casai.uk

With 162 summer rental in or near Chestertown? Look no further than Casai for your upcoming summer getaway. Whether you're traveling with family, friends, or a group, we offer a wide selection of holiday homes and villas designed for the perfect summer retreat.

Our holiday homes and villas in Chestertown come with a range of top amenities, including private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxurious bedrooms, bathtubs, and pet-friendly environments.

Searching for a relaxing retreat in Chestertown to make unforgettable summer memories? Casai has you covered with a variety of options, including unique condos, luxury resorts, bungalows, cozy cabins, RVs, and cottages in Chestertown.

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Frequently Asked Questions About Chestertown Luxury 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 Summer Rentals in Chestertown:

In 2025, Casai offers 162 summer rentals in or around Chestertown. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Chestertown is $371. Check the full list of summer accommodations in Chestertown.
There are 162 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Casai.uk.

Yes, here are some popular summer holiday rentals in Chestertown that have a private or indoor pool:

Check all holiday rentals with a pool in Chestertown on Casai.uk.

Yes, We have 162 summer rental homes in Chestertown and types of place to stay in Chestertown include:

  • Vacation Homes: 162 available for rent
  • Villas: 162 Rentals available for rent
  • Holiday Apartments: 162 Rentals available for rent
  • Hotels with Suites: 162 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Chestertown. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Chestertown.