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

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!

The Place in Cambridge-Easing into winter

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.

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!

River Lure estate - Waterfront, Pool, Hot Tub

River Lure is a beautifully restored historic waterfront home on the banks of the Choptank River, 3 blocks from downtown Cambridge, MD. The 5 bedroom, 3 full/2 half bath waterfront home features a new salt water pool & hot tub overlooking the river, plus a huge yard & private dock. Perfect for families, the entire 3rd floor is a kid's bunk room paradise. Stroll into town to bars & restaurants, River Lure is steps from the Cambridge Marina and Lighthouse; walk to Ironman & Eagleman start.

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.

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.