Holiday rentals with a pool in 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.

"Endless Summer" on the Chesapeake!

A private Oasis! This exceptional 4 bedroom, 3 bathroom Rural waterfront Eastern Shore home sits on over 6 acres and boast endless water activities, including an indoor heated pool! Along with kayaking, crabbing or fishing. You can drift off to sleep in the oversized main suite with a perfect waterfront view! Enjoy the Eastern Shore lifestyle in this beautiful backyard, complete with mesmerizing views and a firepit. Crab or fish from the pier for dinner or take in an amazing sunset! Relaxation!

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.

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.

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 cozy loft is located above the apiary workshop. It is a spacious, kind suite with a walk-in bath featuring a rainforest shower. Windows overlook the donkey pasture, river, farm, and gardens. Designed for a true retreat, there is no WiFi, TV, or smoking. For breakfast, travel on over to Sugar Water Restaurant to have a free breakfast with coffee, tea, juice, and more. The Loft includes a small refrigerator plus coffee and tea essentials. Please note: children are not permitted.

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.

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.

Come for Water Fowl, Hunting-Big, Beautiful Home!

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.

Peaceful Waterfront Home with Pool and Pier

Watch the sunset from the deck, enjoy fishing and crabbing off the private pier, or relax at the private pool or in the hot tub just off the deck in this peaceful neighborhood. Inside, a newly renovated, spotless home with all the upgrades including 4 bedrooms and 3 full baths, one with a beautiful walk in shower. Fully stocked kitchen. Upstairs you will find 4th bedroom/LOFT with 6 twins, a large game room/living room and full bath. This is a no smoking property