Compare Villas, Resorts, & Rentals in Chestertown, Maryland, USA
About Casai's Private Villas and Holiday Rentals in Chestertown
Discover more than 62 vacation rentals available in Chestertown. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chestertown.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chestertown, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chestertown. On average, places to stay near Chestertown offer 950.72 ft², with nightly prices averaging CA $742.
With Casai, finding and comparing holiday rentals in Chestertown is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Chestertown, MD
Frequently Asked Questions About Chestertown?
What are the top holiday rentals in Chestertown?
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Carriage House Hideaway in Middle of Chestertown
- Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
- Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Country Estate in Historic District
- Contemporary waterfront house with private dock & kayaks!
- 350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
- Historic Downtown Garden Oasis with Private Patio
- Breathtaking waterfront home on the Chester River
How many Casai.ca holiday rentals are available in Chestertown?
As of 2025, Casai boasts over 62 properties listed in the Chestertown area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chestertown.
