Holiday rentals with a hot tub in Dorchester County

5 out of 5 average rating, 126 reviews

Home in Woolford

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.

4.97 out of 5 average rating, 62 reviews

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse

Quiet waterfront cozy home w/ pvt pier, hot tub, kayaks, grill, massagechair & fire pit. Experience life on the river in a 2bedrm/1 bath-shower/3bed Retreat on a cove off the ChoptankRiver. About 15-20mins toHistoricCambridge/Restaurants/groceries. Easy day trips to St.Michaels/Tighlman/Oxford/Tubman; 75-90min drive to Ocean City/Rehoboth beach. Waterviews from beds. Relax in screened porch w/ waterviews. Watch sunrise/sunset in pvtpier/kayak/hottub. Bring fishing rods/crablines/baits-seasonal.

Superhost

Cottage in Lusby

4.76 out of 5 average rating, 59 reviews

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

4.98 out of 5 average rating, 101 reviews

Cabin in Lusby

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.

4.93 out of 5 average rating, 151 reviews

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.

5 out of 5 average rating, 78 reviews

Cottage in Woolford

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.

4.98 out of 5 average rating, 116 reviews

Home in Dameron

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.

5 out of 5 average rating, 11 reviews

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.

5 out of 5 average rating, 7 reviews

Home in Lusby

Waterfront home on Mill Creek-5BR-Hot tub & Kayaks

Relax with the whole family at this serene, waterfront retreat on Mill Creek — complete with a hot tub, private dock, kayaks, and nearly 360 degrees of beautiful water views! Cozy up inside or grab beach chairs, sand toys, and books offered for your beach days and return home to grill and dine al fresco on the deck overlooking the water. Let the kids burn off energy on the side yard’s play structure while you relax on the patio by the shoreline, drink in hand.

4.96 out of 5 average rating, 169 reviews

Home in Lexington Park

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.

Superhost

4.9 out of 5 average rating, 119 reviews

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!