Mga matutuluyang bakasyunang may pool sa Dorchester County

Starboard on McKeil Point, w/heated pool & hot tub

Starboard on McKeil Point is a beautiful 5 bedroom, 3.5 bath private waterfront home on five acres overlooking the wide water of Fishing Creek - the perfect compound for families & groups. The house features water views from every turn. Outdoor amenities include a generous screened-in porch, a private dock, a sandy beach, a heated salt water pool & a hot tub. There is also a one bedroom apartment on the second floor of the carpenter's barn which sleeps 6 and includes a full bath and kitchenette.

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" Chesapeake Bay 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!

Serenity Bay-PrivPool-EVChrgr-AskAbout2NightStays!

Now offering 2-night stays!! Send a msg to ask about this! Just added-EV car charger! 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. Lots to do with an outdoor pool, an nicely 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.

Waterfront Oasis-SaltwaterPool/HotTub/FirePit/Dock

Cattail Cove: Your perfect riverside escape! Nestled on 4 scenic acres along the river, our property offers a peaceful respite for family&friends. Sip your coffee overlooking the river as bald eagles dive for their breakfast, and then relax in the heated saltwater pool before crabbing from our brand-new private pier! Included Amenities: -Saltwater Pool: seasonal -Hot tub open all year! -Stone Fire Pit -Kayak, paddle board, canoe -Private boat launch area Max Guest Count is 13 total people

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.

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.

The Place in Cambridge-Spring is in the Air!

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 ( open May 1st - Sept. 30th) 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 Is Fabulous in Winter!

From January, 2026 through March, 2026 come 3 nights and you get 4th free! 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. T

The Loft at Sailor's Retreat. Waterfront Apartment

Romantic waterfront loft for couples in a charming barn. Relax in a cozy king bed, enjoy a full bath, and prepare meals in the well-equipped country kitchen. Sip wine or morning coffee on your private balcony overlooking the water, or explore the creek together with kayaks and paddleboards. Share the pool (April-October), lawn games, and game room with one other rental unit. Perfect for a peaceful getaway to unwind, reconnect, and savor quiet moments together.