Holiday rentals with a pool in Dorchester County

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

"Goose Landing" Waterfront Retreat

Goose Landing! Bring the entire family and the dog! Inground Pool, Kayaks, canoes, fire pit, ping pong all in a country setting! - Bring all your gear - Sitting on over 27 acres and 1000 feet of shoreline, Goose Landing is the perfect private getaway! Catch your own Maryland Blue Crabs right off the pier and cook them up for a feast! This property is the perfect getaway from the hectic life we all live. Dine on the screened porch, Relax by the pool and firepit. Come escape the daily grind!

Family Retreat - Private Pool, 4 Bedroom, Fire Pit

Family fun awaits you at The Oyster House located in the quaint town of Bivalve, MD. This stunning home will welcome you in and wrap you in with warmth! The large open spaces for group gatherings while offering quiet areas to relax and unwind. There are just so many ways to spend the day! Jump in the Pool! Gather together for a family barbeque! Relax by the firepit! Bike to the local tiki bar! Enjoy fishing, crabbing, local beaches, and breathtaking sunsets the Nanticoke River has to offer!

Chesapeake Sunset Retreat

Escape with family or friends to this peaceful, 4-bedroom retreat on the waterfront. With breaktaking views of the river and 7 acres of pristine woods, this is the perfect getway for nature lovers, water enthusiasts, families, and road bikers looking to get away from the hustle and bustle of everyday life. Enjoy coffee or a sublime sunset from a spacious screened porch. Fish, crab, or launch a kayak from the dock. Lounge by the fireplace in the living room or play pool in billiard room.

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.

Big Cozy Loft Overlooking the Farm and River

The Loft is located above the apiary workshop.  It is an expansive king room with bath.  Walk-in shower has a rainforest head. Views of the donkey pasture out your window!   From one side you have a view of the farm & river, the other apiary, gardens & river.  The loft is the perfect place to cozy up.  Each morning you will have a farm fresh breakfast.  The loft has a small refrigerator, tea, coffee with all your necessities. No WiFi/TV or smoking on property. No children in Loft.

Serenity Bay-Priv Pool-ask about 2-night stays!

Now offering 2-night stays!! Send a message to ask about this! Spacious, relaxing, and scenic bay-view house with canoe/kayak access to the Chesapeake Bay. Six bedrooms and 5 full baths provide plenty of space for family and friends to enjoy time together. Plenty to do with an outdoor pool, an abundantly equipped recreation room, and a dock from which to launch your kayak or canoe. Easy access to plenty of activities in the surrounding area makes for a memorable vacation.

The Place in Cambridge-Summer is in the Air!

The pool is open! 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.

Gorgeous, waterfront home - Perfect for Families.

If you were thinking of heading to the Eastern Shore, Casey's Porch is the place to go. Come and see for yourself. Bring your extended Family. Bring your friends. Enjoy the pool. Kayaks and paddle boards and bikes await you at this beautiful home on Hudson Creek. Fish from the dock. Pull crabs from the creek. Walk down quiet country lanes. Sit around the fire pit. So many fun, outdoor things to do. Casey's Porch has it all. First Floor bedroom, also.