Holiday rentals with a hot tub in Dorchester County

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Top-rated hot tub accommodation in Dorchester County

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Top Guest favourite

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.

Home in Cambridge

4.97 out of 5 average rating, 66 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.

Guest favourite

An aerial view captures the expansive property, highlighting a well-manicured lawn, a serene pool area, and a private dock extending into the calm water. Surrounding trees provide shade, while the distant shoreline outlines the tranquil setting.

Home in Tilghman Island

4.95 out of 5 average rating, 37 reviews

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

Top Guest favourite

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

4.98 out of 5 average rating, 111 reviews

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.

Guest favourite

A single-story home features a brick facade and a light-colored roof. The entryway is framed by large windows, allowing for ample natural light. A front porch with rocking chairs is visible. Surrounding greenery enhances the welcoming appearance of the property.

Home in Cambridge

4.85 out of 5 average rating, 20 reviews

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.

Top Guest favourite

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.

Home in Cambridge

4.94 out of 5 average rating, 160 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.

Top Guest favourite

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

5 out of 5 average rating, 80 reviews

Waterfront Cottage & Guesthouse w/Hot Tub

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.

Superhost

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

4.88 out of 5 average rating, 8 reviews

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.

Top Guest favourite

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

4.98 out of 5 average rating, 121 reviews

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.

Top Guest favourite

A spacious living area features light wood flooring and soft blue walls. Comfortable seating arrangements include a large sectional sofa and armchairs. A wooden coffee table sits at the center, while a dining area is visible in the background, showcasing a wooden table surrounded by chairs.

Home in Cambridge

4.96 out of 5 average rating, 25 reviews

Peaceful Waterfront Home with Pool and Pier

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

Top Guest favourite

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

4.96 out of 5 average rating, 172 reviews

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.

Home in Cambridge

4.9 out of 5 average rating, 123 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!

Guest favourite

A bright dining area features a round table surrounded by wooden chairs. A colorful table runner adds a vibrant touch. Large sliding glass doors provide an unobstructed view of the water and open to an outdoor deck. A stylish chandelier hangs from the ceiling.

Home in Deal Island Historic District

4.83 out of 5 average rating, 24 reviews

Reel Relaxation-Waterfront

Reel Relaxation – A Waterfront Escape Nestled on Rock Creek in Chance, MD, Reel Relaxation offers stunning water views, a private dock, and a cozy fireplace. Unwind in the hot tub, gather by the fire pit, or enjoy fresh seafood on the screened porch. Kayak through Rock Creek. With three bedrooms, a pull-out couch, and modern amenities, this retreat sleeps up to 9. Whether fishing, grilling, or unwinding, it's the perfect escape.