Holiday rentals with a hot tub in Dorchester County

4.98 out of 5 average rating, 53 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 Scotland

4.85 out of 5 average rating, 20 reviews

Hays Beach House - Hot Tub - Private Beach

Toasty Hot Tub - Free Wifi - Private Beach - Contactless Check-In - Pet Friendly - Tesla Charger - Linens, Soaps and Shampoo Provided. ChesapeakeBayVacations (ig @ChesapeakeBayVacations) for more pics and information... When you arrive at Hays Beach House and step onto the screened porch, the hot tub is just about ready, promising relaxation with its inviting bubbles. Settling into the warm, swirling waters, the view will unfold — a serene panorama of the bay's gentle ripples under the sunse

4.98 out of 5 average rating, 90 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.

Superhost

Home in Tilghman Island

4.94 out of 5 average rating, 33 reviews

Relax by the Water - Summer Dates Available!

STRN-24-62. Wonderful waterfront home. Minutes from St. Michaels offering all you'll need for the perfect vacation experience. Fabulous location with panoramic views of the water everywhere you look. Crab and fish from the dock. Hop on a bike and explore the island by land and then try out kayaks for a water adventure. Cool off with an afternoon dip in the pool. Enjoy starry nights at the waterfront firepit. If the bikes and kayaks wore you out relax your muscles in the hot tub. Perfect!

5 out of 5 average rating, 65 reviews

Cottage in Woolford

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks

Just 15 minutes from Cambridge on the Eastern Shore you get a waterfront Cottage plus a bonus Guesthouse. Total 3 bedrooms 2 baths. Head to Oxford, St. Michaels and Easton for day trips. Watch beautiful sunsets, kayak or paddle board. Relax on the deck, fish and crab directly off the pier. There’s a a hot tub, gas grill and fire pit. The cottage and guest house accommodates up to 8 people. This property is great for 2-3 couples or families that need a place with more than one bathroom.

5 out of 5 average rating, 61 reviews

River Lure estate - Waterfront, Pool, Hot Tub

River Lure is a beautifully restored historic waterfront home on the banks of the Choptank River, 3 blocks from downtown Cambridge, MD. The 5 bedroom, 3 full/2 half bath waterfront home features a new salt water pool & hot tub overlooking the river, plus a huge yard & private dock. Perfect for families, the entire 3rd floor is a kid's bunk room paradise. Stroll into town to bars & restaurants, River Lure is steps from the Cambridge Marina and Lighthouse; walk to Ironman & Eagleman start.

4.84 out of 5 average rating, 19 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.

4.94 out of 5 average rating, 141 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.

Superhost

Cottage in Lusby

4.8 out of 5 average rating, 46 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 Bungalow 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.

5 out of 5 average rating, 110 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, 9 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.

4.96 out of 5 average rating, 165 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.

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Holiday House Rentals with a hot tub

Private room in Cambridge

5 out of 5 average rating, 12 reviews

Luxury Bedroom 3 night min. 2 Guest, adults only

MilindaRating, 5 stars12 months ago

This is the third time my husband and I have stayed with Bill and it was just as amazing as the first time. His home is beautiful and comfortable to stay in. We found it to be very easy to walk to the start of a nearby race. He was a constant but unobtrusive presence during our stay and was full of information about the surrounding area, from wildlife to great restaurants.

5 out of 5 average rating, 13 reviews

Perfect Eastern Shore getaway Private /waterfront

KikiRating, 5 stars9 months ago

We had a great time at Duane's house in Cambridge. The rental was super fun for us and our three kids - waterfront location, hot tub, lots of places to explore, games, outdoor space, etc. We were in Cambridge for the Ironman race and while this was a little outside of downtown, it was still within a reasonable driving distance to go back and forth. We hope to come back next year! Thanks so much, Duane.

Private room in Cambridge

5 out of 5 average rating, 49 reviews

Wye Three Oaks

SaundraRating, 5 stars2 days ago

I was looking for a quiet, peaceful waterfront experience and was totally delighted with Anna’s home. Anna was so welcoming and open, the home is gorgeous and the setting is idyllic. Each morning I woke up early to sit out on the dock and watch the sunrise while osprey were fishing and geese were flying overhead. Can’t recommend this place highly enough if you are wanting a big exhale.

Home in Deal Island Historic District

The Hideaway

WilliamRating, 5 stars3 weeks ago

This is really a beautiful house, with a great location and with lovely views of the water, fully outfitted, comfortable beds, and lots of special spaces to relax. The perfect place for a holiday weekend for us and our friends. Stephen has thought the whole thing through. We had a lovely time and would return any time.

4.96 out of 5 average rating, 47 reviews

Home in Madison

Bayfront Gem w/ Amazing Water Views + Pond!

AnneRating, 5 stars3 weeks ago

The house was exactly as pictured--lovely, spacious, and welcoming. Right on the water with absolutely gorgeous views and a calming, peaceful vibe! The kitchen was fantastic and well-appointed with high-end appliances and all the pots/pans/utensils we needed to cook family meals. Beds were super-comfortable. The whole house is fully stocked for a wonderful stay. We loved it! Thank you for sharing your amazing home with us!

5 out of 5 average rating, 38 reviews

Home in Lusby

ChesapeakeWaterfront - HotTub_FirePit_Kayak_Arcade

LeenyRating, 5 stars1 week ago

We had a wonderful stay! The house was absolutely charming—beautifully decorated, clean, and perfectly situated on a peaceful lake. It offered the best of both worlds: a quiet, relaxing retreat while still being just a short drive from town if we needed anything. Julie was an exceptional host—kind, helpful, and incredibly responsive. We truly couldn’t have asked for a better experience. I highly recommend both the home and Julie as a host—you won’t be disappointed!

Home in Deal Island Historic District

4.83 out of 5 average rating, 6 reviews

Reel Relaxation-Waterfront

CrystalRating, 5 stars2 days ago

The location was very beautiful. It fit our family of 6 comfortably. I appreciate the air conditioning and how cool it felt from the hot temps outside. There was lots of wood already available to make a fire, hot tub was ready to use, lots of available items already in the house for use. Anything you could want or need, she basically had. It’s also accessible to day trips near by - about an hour or so to the beaches. Very secluded and peaceful.