Holiday rentals with a pool in Dorchester County

Tranquility on Tilghman Island – Wide Water Views

Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shore, or lounging by the pool with a good book. Just minutes from charming St. Michaels, this 4-bedroom retreat blends coastal charm with modern comfort — perfect for families, friends, or a romantic getaway. In the evenings, grill, gather around the firepit under the stars, and let the day fade away in the bubbling hot tub. Guests love the spacious layout, the dreamy screened-in porch for

Location · Family · Wifi

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

Family · Value · Wifi

"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!

Location · Family · Hospitality

Private Waterfront Cottage with Pool and Poolhouse

Totally Private, quiet, deep 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 at cottage, pool, lawns, and gardens; all for the exclusive use of cottage guests. Located between the beautiful villages of Easton and Cambridge -- close to Trappe, Oxford, and St. Michaels. STRN-26-13

Location · Family · Check-in

Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!

Now offering 2-night stays!! Send a msg to ask about this! Just added-Hot Tub! Spacious, relaxing, and scenic bay-view house with canoe/kayak access to the Chesapeake Bay. We've just put in a hot tub!!! Photos will be taken when it stops raining. Six bedrooms and 5 full baths. 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.

Family · Value · Outdoor spaces

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 additional upstairs lounge. We are long term 5 Star Airbnb hosts who live nearby.

Location · Value · Beach

Waterfront Oasis: SaltwaterPool&HotTub&PrivateDock

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

Family · Location · 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.

Value · Family · Laundry

The Place in Cambridge-Summer is here!

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.

Value · Family · Getting around

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.

Family · Location · View

Modern Chesapeake Waterfront - Heated Pool - Dock

Chesapeake Dream is a stunning renovated waterfront farmhouse on 5.6 acres with breathtaking Chesapeake Bay views — perfect for families & friend groups. Boat, fish, crab & hunt at this outdoorsman's paradise. Watch the sunset from the screened porch, gather around the bayside fire pit, or BBQ poolside. With historic landmarks, hiking, golf & charming towns nearby, every day brings a new adventure. Hosted by Wander Home - see "Other Things To Note" in the description below.

Location · Family · Sleep quality

Gorgeous, Waterfront Home Is Perfect for Families!

Looking for a large, beautiful house for a big family get-away? 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.

Value · Location · Condition