Chestertown Cottage Rentals & Holiday Homes

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

About Chestertown Cottage Rentals on BedroomVillas.ca

Seeking incredible premium cottages to rent near Chestertown? BedroomVillas features more than 12 cottages that are ideal for your next trip. Discover high-end 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 attractions, to give guests the best travel experience they could ever wish for. BedroomVillas’ cottage listings come in all shapes and sizes for large groups, friends, or couples in Chestertown.

Are you planning to travel to a lakeside, beach, or mountain area? Then we've got the places for you. BedroomVilla’s cottage rentals and boutique resorts and rentals offer a great selection, giving you direct access to the owners of these cottage properties, and providing you the best opportunity to find a great price for a great stay.

BedroomVillas offers 12 luxury holiday cottages and places to stay in Chestertown. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget. Relax with BedroomVillas.

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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 $222 per night. BedroomVillas.ca 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 BedroomVillas.ca

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 BedroomVillas.ca 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 BedroomVillas.ca
Yes, there are luxury cottages in Chestertown. Find more luxury, lakefront, winter, & last-minute cottage rentals near Chestertown.