House vacation rentals in Dorchester County

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Top-rated house rentals in Dorchester County

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Guest favorite

Home in Church Creek

4.78 out of 5 average rating, 161 reviews

Waterview cottage on Chesapeake Bay

(The crabs will be running soon, it getting warmer. Great view of the Chesapeake Bay. The Access to the Bay through canal behind the house. Private beach just five minute kayak ride from the house. Bring your own kayaks or rental them from Blackwater Adventures ask for Matt . There floating dock for a kayak launch. Now easy for you to get in and out of your kayak. New picnic table on porch that seat 6 people and two new beds. Two crab traps set for you and also a holding pen on the property.

Nov 22 – 29

R3,239 ZAR per night

Guest favorite

Home in Lusby

4.99 out of 5 average rating, 114 reviews

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Coastal Oasis On The Chesapeake (PARTY & 4•20 FREE zone) is where you come to: RELAX, DECOMPRESS and RE-CHARGE! You'll experience all the tranquility & majestic beauty of PEACEFUL living on the Chesapeake Bay. You'll awaken to breathtaking & alluring sunrises while also being surrounded by nature's wooded bliss of starry nights. Located 4 miles from Solomon's Island. Contact host for pre-approval of pets, pet fee applies. Unregistered: guests/pets & smoking including marijuana will incur fines!

Oct 16 – 23

R10,029 ZAR per night

Guest favorite

Home in Cambridge

4.98 out of 5 average rating, 107 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Come relax at our pristine waterfront home. We offer 4 bedrooms w/7 beds for 10 guests. We are nestled in a small neighborhood on the beautiful Choptank River w/ a new private pier. We provide bikes, kayaks, paddleboards & yard games. Just want to relax? Come bask in the sun in the hammock or on the waterfront w/pier. Try fishing off the pier or simply chill on the back deck or patio. At night hang out by the firepit. Explore downtown Cambridge - it's a short walk or bike ride to town.

Nov 23 – 30

R11,727 ZAR per night

Guest favorite

Home in Cambridge

4.99 out of 5 average rating, 142 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Mar 24 – 31

R8,334 ZAR per night

Guest favorite

Home in Oxford

4.96 out of 5 average rating, 185 reviews

The Oxford House

Enjoy water views from the backyard or visit with friends on the screened in porch. The light and airy, 3bd, 2bath house is a short walk to Oxford’s best restaurants and favorite ice-cream shop. You can find the best beach in oxford only 75 yards from our front door or take the Ferry to the neighboring town of Saint Michaels, Maryland. You will love the scenic views and historical charm of this little town, the Oxford house has a central location allowing you to walk or bike to everything.

Aug 19 – 26

R5,951 ZAR per night

Guest favorite

Home in Lusby

4.94 out of 5 average rating, 157 reviews

Waterfront Home on the Chesapeake Bay-Pvt Beach

A commanding view of the Chesapeake Bay. Enjoy walking the beach to Calvert Cliffs, bike to parks, art and cultural events. Enjoy the private beach with plenty of fine sand and gentle waves, great for teaching little one's water skills, playing with your canine companion or fishing/crabbing off the beach. You’ll love this waterfront hideaway because of the location, views, and the ambiance. My place is suburb for couples, solo adventurers, business travelers, families, and canine friends.

Nov 25 – Dec 2

R7,450 ZAR per night

Guest favorite

Home in Cambridge

4.95 out of 5 average rating, 101 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.

Dec 10 – 17

R4,788 ZAR per night

Guest favorite

Home in Woolford

4.93 out of 5 average rating, 118 reviews

Waterfront Getaway with Dock

Bicyclist's and outdoorsman's dream! Beautiful rancher on two waterfront acres just 4 miles from Blackwater Wildlife Refuge and Harriet Tubman National Park. 10 minute drive from downtown, the Hyatt, and the Ironman starting point as well. Ironman and Eagleman races actually pass right by! Bright, sunny, and newly renovated, it's a great place to hang your hat after a day of hunting, fishing, bicycling, or triatholon-ing! Or just take a weekend to relax on the water!

Oct 21 – 28

R4,275 ZAR per night

Guest favorite

Home in Lexington Park

4.97 out of 5 average rating, 139 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.

Sep 17 – 24

R7,629 ZAR per night

Guest favorite

Home in Lusby

5.0 out of 5 average rating, 135 reviews

Cove Point Beach Home 1 &1/2 blocks to Beach

"Welcome to our Beach House, located in the unique peaceful private beach community of Cove Point. You'll enjoy the tranquility and the beauty of living less than a 2 min walk to the sandy beach and just a few away from Solomon's Island, MD. Our home was just renovated and is ready for your family to enjoy, offering beach necessities (wagon, chairs, umbrella, & toys) and recreational equipment (bikes & kayaks). This will be your home away from home.

Jan 6 – 13

R4,094 ZAR per night

Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 180 reviews

Guest House: Farm homestead

Quiet country guest house with 1 BR/ 1 BA, queen sleeper sofa and fully stocked kitchen. Coffee/creamer/sugar provided. Come relax & enjoy the row boat and paddle boat, fishing in the ponds (C&R, No Pond Access from August 24 thru January 30 annually), grill on the deck, watch the bikers roll by (Ironman course) or finish your day by the fire-pit with s'mores! All this and only 3 miles to town and on the Eagle Man and Iron Man race course.

Oct 10 – 17

R2,360 ZAR per night

Guest favorite

Home in Lusby

4.99 out of 5 average rating, 175 reviews

Cove Point Cottage with Chesapeake Bay views

Cozy beach house just one block from the sandy Cove Point Beach on the Chesapeake Bay. Grab the beach wagon from the shed, load up with beach chairs, towels and your cooler and take a short stroll to enjoy a day at the beach searching for sharks teeth, shells and swimming in the bay. Rinse off in our outdoor shower and enjoy a relaxing evening by the fireplace, reading in the sunroom overlooking the bay or on the outdoor shady patio

Nov 7 – 14

R4,815 ZAR per night