Holiday rentals with a hot tub in Dorchester County

Hot Tub Hideaway by Shark Tooth Shores

With views of the Chesapeake Bay, access to private beaches, a brand new hot tub, air hockey table, kayaks, and being just minutes away from hot spots like Calvert Cliffs and Solomon's Island the Hollow makes for the perfect vacation destination. Enjoy sunrise views through the treetops each morning on the expansive back deck, or use our eco-friendly wood burning stove for autumn and winter nights. Unlike many beach houses, this home is surrounded by trees making it serene. UPDATED PHOTOS SOON

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.

Hambrooks Home with Hottub/Mid Term stays welcomed

Welcome to my 2 bedroom/2 bath, an office(with 2 smaller 72x38 inch floor mattresses) so you can keep your nose to the grindstone if desired, and also a Hot tub! The Home is situated a stones throw outside of the city limits, but close enough to Downtown, The Choptank River, and all the area has to offer. Watch the sun rise on the front porch with a cup of coffee, or enjoy the back deck and Hot tub while the sun sets. Reading material, games, and fun stuff for the kiddo's also obtainable.

Waterfront Cottage & Guesthouse Near Cambridge

Escape to a serene waterfront oasis just 15 minutes from Cambridge on Maryland's picturesque Eastern Shore. This charming Cottage and separate Guesthouse offer a perfect blend of relaxation and adventure, with stunning Chesapeake Bay sunsets, direct water access, and modern amenities for an unforgettable getaway. Ideal for 2-3 couples or families, this pet-friendly property sleeps up to 8 guests across 3 bedrooms and 2 bathrooms, ensuring comfort and space for everyone.

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.

Historic and Spacious Stewart House

This 18th Century Victorian home has been lovingly restored and furnished. It boasts 8 beautifully appointed bedrooms (2 king, 5 queen and 1 double twin rooms) and 5 1/2 baths, formal dining room, eat-in kitchen, den, laundry room, two working fireplaces, upper deck, large, landscaped backyard with a jacuzzi spa, firepit, large outdoor seating area with barbeque and more. Convenient location on High Street just blocks from downtown restaurants, bars and boutiques.

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.