Holiday rentals with a pool in Dorchester County

Private Waterfront Cottage on Bolingbroke Creek

Totally Private, quiet water-front cottage with wood-burning fireplace and exclusively private 60' Lap Pool (open mid-April to mid-October), large open Pool House and Pier. The nearest residences in the area are far removed from this cottage for a great feeling of seclusion and privacy for the cottage, pool, lawns, and gardens; all for the exclusive use of the cottage guests. Located between the beautiful villages of Easton and Cambridge -- close to Trappe, Oxford, and St. Michaels. STN-22-17

"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!

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 heated 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.

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

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.

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.

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.