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Chestertown Cottages & Holiday Homes

Find the best cottages in Chestertown - We found 108 exact matches

About Chestertown Cottage Rentals on Hotala.uk

Searching for cottages to rent near Chestertown? Hotala features more than 108 cottages that are perfect for your next trip. Discover luxury cottage rentals and small B&Bs 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. Hotala’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? Hotala’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 cottage at a great price.

Hotala boasts of 108 holiday cottages, small inns, and other places to stay in Chestertown. The site provides unique 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. Get last minute and hot deals on Hotala.

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Frequently Asked Questions About Chestertown Rental Cottages

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 Cottage Rentals in Chestertown:

The average cost for a cottage rental in Chestertown is $363 per night. Hotala.uk 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 Hotala.uk

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 Hotala.uk shows that there are Over 108 private swimming pools or cottages with indoor pools in the Chestertown area along with other great amenities.
About 108 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 Hotala.uk
Yes, there are luxury cottages in Chestertown. Find more luxury, lakefront, winter, & last-minute cottage rentals near Chestertown.