Holiday rentals with a pool in Dorchester County

Chesapeake Bay Retreat! Spectacular Views!

Chesapeake Bay Retreat is a beautiful waterfront property with amazing westerly sunsets, a guest house, pool, and breathtaking ocean liner views of the Chesapeake Bay. This waterfront paradise offers endless space and options for fun: Pool, kayaks, grilling, bonfires, fishing & crabbing. The guesthouse has a TV room and private bathroom that sleeps 6. Far enough away from all the chaos of life, but a short drive to restaurants, museums and shopping. A Public boat launch 1.5 miles away! Paradise!

Spacious and private waterfront, sleeps 10

Are you looking for a family getaway or a peaceful location to telework? This property offers it all. Tastefully remodeled waterfront property with a large private salt water pool, dock for fishing, crabbing and kayaking. One-floor open plan with two large decks. Great for entertainment in privacy and is in proximity to restaurants, vineyards, beautiful beaches and parks of Chesapeake Bay and Patuxent River. Just 1 hour to the south of Washington DC and within minutes to NavAir base and Excelon

The Place in Cambridge-Sailing into Autumn

The pool is open through September 30th Beautifully located, a clean crisp poolhouse cottage with key extras.! Queen bed, full kitchenette, and beautiful bath. Enjoy the lovely in-ground pool & poolside seating. Perfect for couples or small families. A block from the Choptank River, 1/2 mile walk downtown to shops and dining. Experience the Eastern Shore of the Chesapeake from a new perspective-it's your stay! The Place in Cambridge, sometimes, the best experiences come in simple packages.

RELAX, You're on RIVER & POOL time!

Come stay at this centrally-located home with beautiful views of the Choptank River. Enjoy sun filled days by the custom built pool and quiet nights by the gas fire pit. Adults and children will love the pool house/game room where you'll find an open air bar, full bathroom, 70" television, shuffleboard, ping pong and foosball. The house is newly renovated with 3 bedrooms 2 bath (1 in pool house) sunroom, and upstairs kids lounge. We are long term 5 Star Airbnb hosts who live nearby.

Waterfront Property & Pool near Ironman Race

Escape to tranquility on our serene 1-acre property, perfect for birdwatching enthusiasts. Enjoy exclusive access to a private dock, two kayaks, fishing and a refreshing in-ground saltwater pool. Unwind in our spacious 5-bedroom, 2.5-bathroom home, equipped with TVs, streaming services, and high-speed internet throughout, allowing you to stay connected while you relax. Conveniently located 10 min from the Hyatt & 15 min from Historic/ downtown Cambridge. Your peaceful retreat awaits!

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Welcome to our waterfront paradise overlooking the Chesapeake Bay! Experience comfort and tranquility at this extraordinary retreat, where breathtaking views and unforgettable memories await you. This serene beachfront property is little over an hour from DC & Northern Virginia, and about 90 minutes from Baltimore. With private pool, fire pit, kayaks, paddle boards, pingpong, weights & workout equipment, it's a perfect place to recharge and make memories with family and friends.

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Our closest neighbor is across a cove. Our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

Turtle's Nest - Hist. Cambridge

Charming 100 year old home with a pool in the Cambridge Historic District! Perfect location for Ironman/Eagleman!! And just 10 short min to Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina. Come enjoy all that Turtle's Nest has to offer! Plenty of space with 5 bedrooms, a well outfitted kitchen, screened in porch, manicured grounds and of course .... a lovely pool! Walk to town, the races, the yacht club and restaurants or just stay and relax.

The Loft at Sailor's Retreat. Waterfront Apartment

Come spend a few days in our cozy efficiency barn apartment overlooking the water. There is a King bed, a full bathroom with shower, and a country kitchen with everything at your fingertips. Enjoy the views from the balcony or feel free to use our kayaks or paddle boards to explore the creek more closely. Even if it rains, you have a full game room just below your loft apartment. Full use of the swimming pool, yard games and watercraft are included.