Holiday rentals with a hot tub 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.

Waterfront Cottage Near Cambridge w/Hot Tub

Amazing property with fantastic water views, a hot tub and a fire pit surrounded by comfortable Adirondack chairs. This charming Cottage and separate Guesthouse offer a perfect blend of relaxation and adventure. Offering stunning Chesapeake Bay sunsets, beautiful pier for crabbing or fishing and a hot tub for soaking. Ideal for 2-3 couples or families, this pet-friendly fully fenced property sleeps up to 8 guests. A short 15 minute drive to Cambridge. Take day trips to Easton, St. Michaels.

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

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Welcome to The Lake House - our freshly updated 3 bedroom, 3 bath cabin on Lake Vista with views of the Patuxent River/Chesapeake Bay from the private pier. Enjoy everything Southern Maryland has to offer all within a 10 minute drive - Calvert Cliffs, Flag Ponds, Solomons Island - hiking, fishing, boating and beaches. Located just 90 minutes outside DC, The Lake House will become your new go-to retreat from the hustle. Come relax and make memories on the water with your family and friends.

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

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Hoopers Island Retreat

Welcome to Hoopers Island retreat – a newly renovated coastal getaway with stunning waterfront views. This light-filled home features 3 bedrooms, 2.5 bathrooms, a full kitchen, spacious living area, and outdoor spaces made for relaxation—covered porch, hammock swings, sun loungers, dining set, and a private dock perfect for crabbing, kayaking (which are available at the property), or watching the sunset. A peaceful escape for families or friends to unwind by the water.

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Peaceful Waterfront Home with hot tub

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

Private beach retreat in historic St. Mary's City

Nestled next to historic St Mary's City and a lovely state park, your Lucas Cove Beach home awaits you with your own private sandy beach and pier with vast views of the water, new salt water hot tub steps away from the beach, four beautifully furnished bedrooms with Casper mattresses, an upstairs deck with adirondack chairs to take in the water views and amazing sunrises while sipping a beverage or just relaxing, high speed Wi-Fi. Kayaks avail for rent.

Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8

HOT TUB!! WATERFRONT!! Relax with the entire family at this peaceful 3 bedroom fully remodeled private waterfront cottage on a quiet cove off the Choptank River/Chesapeake Bay. Enjoy the incredible views from your bed, from the large screened-in porch, from the oversized deck, from the hammock or double swinging chair out by the water! Launch a kayak right from the property and watch the gorgeous sunrises from the comfort of your bed!

Beachfront Escape with Horizon Views of the Bay

Modern beachfront Panabode log cabin with sweeping Chesapeake Bay views. Relax on the deck, in the hot tub, swing, beach, or by the fire pit. Enjoy kayaks, paddleboards, shallow water, landscaping, and wildlife sightings. Main bedroom has king bed and ensuite bath. No pets, visitors, or street parking. Guests must bring linens, towels, and remove trash. Peaceful beachfront escape with modern, rustic charm, and unforgettable views.