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
• 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!
• The Waterfront Retreat- With Sauna and Hot Tub!
• Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River

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
• Circa 1900 Home in the Heart of Historic Downtown Chestertown

Yes, there are 54 self-catering vacation homes in Chestertown that have hot tubs, swimming pools, & other amenities.

There are more than 54 luxury villas and vacation homes in or near Chestertown. Filter by price to compare find the most expensive places to stay on Villakanaya.

Yes, there are 54 pet friendly vacation homes and places to stays that are available in or near Chestertown that you may consider.