Chestertown Cottage Rentals & Holiday Homes

Find the best cottages in Chestertown - We found 12 exact matches

About Chestertown Cottage Rentals on Rent By Owner

Searching for cottages to rent near Chestertown? Rent By Owner features more than 12 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Chestertown have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. RBO’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Chestertown.

Are you planning to travel to the lakeside, beach, or mountain area? RBO’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Rent By Owner boasts of 12 holiday cottages and places to stay in Chestertown. The site provides unique Airbnb, VRBO, RBO-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

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Chestertown Cottage Rentals Frequently Asked Questions

The average cost for a cottage rental in Chestertown is $230 per night. RBO has a wide list of great cottages near Chestertown that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Chestertown that allow you to bring your pet:

See all pet-friendly vacation rentals in Chestertown on Rent By Owner

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Chestertown to find one that works for you.
As of 2025, the data from Rent By Owner shows that there are Over 12 private swimming pools or cottages with indoor pools in the Chestertown area along with other great amenities.
About 12 cottages in Chestertown boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Chestertown on Rent By Owner