Chestertown Rentals By Owner

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 Vacation 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
• Eagles Point Landing
• Breathtaking waterfront home on the Chester River
• Historic Manor House on Beautiful Eastern Shore Estate
• The Lazy River House
• Victorian Hideaway: Beautiful Exterior, Modern interior
• Escape to Goose Landing: Your Waterfront Retreat in Chestertown!
• River Cottage, Chestertown

There are many large, family-friendly vacation homes available in Chestertown; however, here are the most popular family rentals listed on our site:

• Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
• Chestertown Family Hideaway with Kayaks and Deck!
• The Lodge at Great Oak Landing
• Country Estate in Historic District

Yes, there are 56 self-catering vacation homes in Chestertown that have hot tubs, swimming pools, & other amenities.

There are more than 56 luxury villas and vacation homes in or near Chestertown. Filter by price to compare find the most expensive places to stay on Chartersbyowner.

Yes, there are 56 pet friendly vacation homes and places to stays that are available in or near Chestertown that you may consider.