Holiday rentals with a hot tub in Dorchester County

5 out of 5 average rating, 81 reviews

A hot tub is situated outdoors with a view of the water and nearby pier. The setting sun reflects off the water's surface, creating a serene ambiance. Surrounding the hot tub are trees and space for outdoor seating.

Cottage in Woolford

Amazing Bay Views Cottage W/Guesthouse & 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.

4.95 out of 5 average rating, 38 reviews

A spacious waterfront home is presented with a clear blue sky overhead. A well-maintained lawn surrounds a rectangular pool, with lounge chairs and umbrellas positioned nearby. The exterior features large windows and a covered porch, inviting relaxed outdoor living.

Home in Tilghman Island

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

4.97 out of 5 average rating, 117 reviews

A serene outdoor setting features a hot tub surrounded by trees, overlooking the lake. A wooden pathway leads from the hot tub to the pier, where boats can be launched. A fire pit with seating is nearby, inviting relaxation in nature.

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.

5 out of 5 average rating, 16 reviews

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

A spacious backyard features a circular fire pit surrounded by Adirondack chairs. A picnic table sits to one side, and a hot tub is partially shielded by evergreen trees and a wooden fence, providing a serene outdoor retreat.

4.93 out of 5 average rating, 166 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.

4.9 out of 5 average rating, 10 reviews

The exterior of the coastal retreat features a light blue facade and large covered patio. Comfortable seating areas and hammock swings are positioned on the grassy lawn, while potted plants add a touch of greenery. The evening sky displays soft hues as the home is gently illuminated.

Home in Fishing Creek

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.

4.98 out of 5 average rating, 124 reviews

A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.

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.

An aerial view showcases the expansive property with lush green lawns, dotted by trees and water features. The main house is centrally located, surrounded by a driveway, a guest house, and a parked vehicle. Nearby, a private fishing pond is visible, along with the waterfront.

5 out of 5 average rating, 9 reviews

The Point at Little Choptank

Take it all in and relax at this beatiful Cambridge waterfront getaway on nearly five acres. It boasts a guest house with its own kitchen, 2 bedrooms and bathroom. The main house has 2 fireplaces, 2 large family rooms with a gourmet kitchen. Master suite has a freestanding tub. Sun room, pool, deck, private dock, large playground and stocked fishing pond. Hang out in a hammock, take a swim, go fishing or play in the game room. This place has something for everyone.

4.93 out of 5 average rating, 14 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, 173 reviews

A wooden pier extends over calm water, leading to a two-story home with large windows and a welcoming deck. Brightly colored chairs sit in the yard, alongside a grassy area and trees. Two kayaks are visible on the pier, ready for use.

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

A scenic waterfront view is captured, featuring a spacious green yard with a double swing and a hammock situated under a tall tree. Calm waters reflect the sky, creating a serene atmosphere. Lush greenery lines the shore, enhancing the peaceful setting.