Vacation rentals in Pooles Island

Cozy, clean & spacious lower level of a new home

This is a spacious lower level of a newly built home. This private guest area has a lounge, dinning, and kitchenette in addition to a bedroom and a bathroom. Guests share only the main entrance of the townhouse with owners who live upstairs. This private decorated space includes a smart TV, comfortable seating, dining for 4, microwave, coffee maker, full refrigerator, toaster/air fryer, queen bed, wardrobe & dresser. Washer/dryer available upon request. Please review house rules before booking

Waterfront Romantic Studio

Unwind at our private studio getaway-featuring an updated kitchen & bathroom, and cozy sleeping area. Separate entrance for complete privacy. Step out onto the shared deck and take in stunning water views, perfect for your morning coffee or a relaxing evening drink enjoy the waterfront vibe. Make memories around the fire pit or explore nearby state parks with scenic hiking trails and beaches. Whether you’re here for a show, a convention, or just some sightseeing, only 20 minutes from Baltimore.

RetroLux Guest Suite 20 min to Downtown Baltimore

Retro-Lux Suite has the feel of a luxurious separate apartment with all the necessities you may need during your stay; from a warm and cozy bedroom, a clean and airy bathroom, to an inviting bright living room/kitchenette combo well stocked for your needs. The icing on the cake is a fantastic zen-like sunroom to enjoy your morning coffee/tea, or a glass of wine in the evening. Best of all, it's on the first floor, easy to get in and out; you can't go wrong staying at this unique guest suite.

Cozy Waterfront Cabin Escape

Want to escape the city for a night or week and spend time sitting by the water reflecting and taking it all in, this is the cabin for you. Two (2) bedroom, 1.5 bath shore cabin (600 sqft) that provides the perfect balance of indoor charm with outdoor access and enjoyment. Bring your kayaks and launch them from the dock and explore beautiful Seneca Creek or just sit and relax in the hot tub. High-speed internet makes this a great working location as well with raise/lower desk and 2nd monitor.

The Waterside Nest

Escape to this serene 3-bedroom, 2-bath waterfront home in Middle River, blending modern coastal design with nature’s tranquility. Enjoy lounging on the deck with stunning beach and water views, fish from the shared pier, or kayak on calm waters. Inside, unwind in the open living area, cook in the chef’s kitchen, and relax in the luxury master suite. With a sandy beach, fire pit, hot tub, and easy access to dining, shopping, and attractions, this retreat is ideal for relaxation and adventure.

Chestertown Private cottage with NFL Sun Ticket

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

Chesapeake Getaway | Marinas | Woodland Views

Escape to our peaceful retreat on Maryland's Eastern Shore, nestled in a quiet, wooded neighborhood near historic Chestertown. The Chesapeake Bay is known for its wildlife and serene landscapes. This cozy haven is perfect for unwinding and reconnecting with nature. After exploring Chestertown's charming streets, local shops, and delightful restaurants, or kayaking at nearby Worton Creek, relax in our comfortable home, where you can read, play games, or enjoy the peaceful surroundings.

Sweet Bay Overlook

Take it easy at this unique home overlooking the Chesapeake Bay. You will enjoy watching the amazing sunsets on the bluff as the eagles, ospreys and boats drift by. Our little house was built in the 1960’s by a brick mason who was very good at his trade. In recent years, the home had fallen into disrepair, but a talented Amish craftsman purchased the house and renovated it from top to bottom. The Sweet Bay that you see today reflects his incredible attention to detail and quality.

Lotus House: spacious, private, expansive views

Relax and spread out in this modern yet perfectly appointed Eastern Shore Home. Neighboring the Chesapeake Bay and situated on a quiet and private road, you will be surrounded by preserved farmland and woods. Peer through the trees for a partial water view and fabulous sunsets. Fresh steamed crabs and other local seafoods are available for pick up just 2 miles away. Or try out the waterfront restaurant, beach bar, or rent a boat slip at Great Oak Landing Marina just a mile away.

The Waterfront Retreat- *With Sauna and Hot Tub!*

Welcome To Paradise! Experience Waterfront luxury at this renovated retreat in a very quiet Chestertown neighborhood. The home features an open layout, spacious living room with sweeping bay views and a private beach. Enjoy the private guest house, In ground pool, and spacious deck for some of the most beautiful sunsets you've ever seen. Just minutes from historic downtown, experience comfort with coastal charm—perfect for relaxing, entertaining, or exploring the Eastern Shore.

Relaxing Waterfront - Golf Course & Sunset Views

Our home away from home in Chestertown is truly an extraordinary property. Water and golf course views from every room. And wildlife! Some of the birds and animals we've seen: - blue herons - bald eagles - ospreys - ducks - turtles - otters Inside, there's room enough for 8, with 3 bedrooms and 3 full bathrooms, including one of each on the main level. Just one mile from downtown Chestertown, and a short walk to Chester River Yacht & Country Club

A unique place on sue creek

Enjoy your private apartment and deck on the water or come sit down by the waterfront and watch the Ospreys, herons, ducks and the occasional eagle. Fishing off the pier and possible small boat docking available. We are close to Rocky Point golf club, Baltimore yacht club, 20 minutes from Camden Yards and M&T stadium. We are 38 minutes from BWI. You will have private parking in a quiet safe neighborhood. Sorry, no pets allowed.