Vacation rentals with a hot tub in Dorchester County

4.96 out of 5 average rating, 46 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

Hot tubOutdoor spacesSleep quality

5.0 out of 5 average rating, 91 reviews

A serene water view is captured as the sun sets, casting warm hues of orange and pink across the sky. The calm surface of the water reflects the colorful clouds, while a pier extends into the scene, inviting leisure and tranquility.

Cottage in Woolford

Bay Cottage w/ Pier-Kayaks near Cambridge

Amazing property with pier for family fun. Try crabbing , fishing or kayaking off this waterfront property. At night, sit around the fire pit or soak in the hot tub. This area is one if the best kept secrets of the Eastern Shore offering stunning Chesapeake Bay sunsets. Ideal for 2-3 couples or families, this pet-friendly fully fenced property sleeps up to 8 guests. There is a main house with 2 bedrooms and the new guesthouse sleeps up to 4 people. 15 minutes to Cambridge. Near Blackwater.

BathroomOutdoor spacesAccess

A large window fills the space with natural light, offering views of the tranquil waterfront and grassy area. A small desk and chair are positioned nearby, while outdoor seating is visible on a stone patio outside.

4.97 out of 5 average rating, 72 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.

Hot tubBathroomNearby

4.85 out of 5 average rating, 100 reviews

An aerial view showcases a lush green landscape surrounding a peaceful shoreline. The sandy beach meets calm waters, framed by dense trees. The varied colors of the water create a serene contrast against the vibrant greenery, presenting a tranquil natural setting.

Cottage in Lusby

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

BathroomOutdoor spacesAccess

5.0 out of 5 average rating, 22 reviews

Home in Lusby

Private Beach, Dock, Hottub @ Solomons Bay A-Frame

Welcome to your A-frame waterfront cottage with private sandy beach & dock, hot tub, firepit, Pac-Man arcade, renovated & re-launched May 2026! 4 BR, 2 full baths, just minutes from Solomons Island, Calvert Cliffs, & an easy 1h 15min drive from DC. Central AC & heat, fast WiFi, full kitchen, ample parking, room for a trailer. Swim, fish, crab, kayak, paddleboard, or unwind from the private dock or sandy beach as the sky glows at sunset—the perfect place to make memories with friends & family.

Outdoor spacesHot tubCondition

4.93 out of 5 average rating, 106 reviews

Home in Lexington Park

Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!

Now offering 2-night stays!! Send a msg to ask about this! Just added-Hot Tub! Spacious, relaxing, and scenic bay-view house with canoe/kayak access to the Chesapeake Bay. We've just put in a hot tub!!! Photos will be taken when it stops raining. Six bedrooms and 5 full baths. Lots to do with an outdoor pool, an nicely 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.

Hot tubOutdoor spacesComfort

5.0 out of 5 average rating, 30 reviews

Waterfront Oasis: SaltwaterPool&HotTub&PrivateDock

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

Outdoor spacesHot tubBackyard

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.

4.94 out of 5 average rating, 187 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.

BathroomOutdoor spacesWalkability

4.96 out of 5 average rating, 189 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 newly renovated 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 available for rent.

Outdoor spacesHot tubLocation

4.99 out of 5 average rating, 142 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.

BathroomHot tubAccess

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.

4.88 out of 5 average rating, 141 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!

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