Great Oak Landing Rentals By Owner

There are a lot of options in Great Oak Landing. If you plan on staying in the Great Oak Landing area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Great Oak Landing:

• Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
• Stay in the landmark Lighthouse!
• Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
• Carriage House Hideaway in Middle of Chestertown
• 200 steps to the beach!
• Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
• Circa 1900 Home in the Heart of Historic Downtown Chestertown
• Waterfront Paradise on the Eastern Shore of Chesapeake Bay
• Country Estate in Historic District
• Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

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

• Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
• Bamboo Sands Villa and Captains Lookout
• Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
• Chestertown Family Hideaway with Kayaks and Deck!
• The Lodge at Great Oak Landing
• Stay in the landmark Lighthouse!

Yes, there are 2 self-catering vacation homes in Great Oak Landing that have hot tubs, swimming pools, & other amenities.

There are more than 2 luxury villas and vacation homes in or near Great Oak Landing. Filter by price to compare find the most expensive places to stay on Sonomavillas.

Yes, there are 2 pet friendly vacation homes and places to stays that are available in or near Great Oak Landing that you may consider.