House vacation rentals in Dorchester County

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Top-rated house rentals in Dorchester County

Guests agree: these houses are highly rated for location, cleanliness, and more.

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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 26 – Dec 3

G$36,795 GYD 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 23 – 30

G$110,662 GYD 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 26 – Dec 3

G$129,437 GYD per night

Guest favorite

Home in Cambridge

4.97 out of 5 average rating, 64 reviews

Roslyn Retreat. Center of the Eastern Shore!

Neat, clean and comfortable older home with eastern shore charm and eastern shore décor. More of a home feeling. Great location and safe neighborhood and conveniently located 2 blocks off Rt. 50. Walking distance to local restaurants and the Choptank River. Close to Eastern Shore activities, hunting, fishing, golf, exploring and all Cambridge that has to offer. Relaxed setting. This is not the Hyatt, it's around the corner, but it's not the hotel experience you want or want to pay for is it?

Aug 28 – Sep 4

G$27,525 GYD 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.

Feb 2 – 9

G$88,813 GYD per night

Guest favorite

Home in Cambridge

4.97 out of 5 average rating, 94 reviews

Church Creek Charm (close to Blackwater Refuge)

Charming Eastern Shore home with new kitchen & bathroom. Less than 10-15 mins from Cambridge, Blackwater National Wildlife Refuge & the Harriet Tubman Underground Railroad museum. Ideal spot for cycling, birding, fishing, canoeing, relaxing or exploring the many cute towns of Maryland's Eastern Shore. Just over an hour from Ocean City & Assateague Nat'l Seashore. Pet friendly with fenced backyard. The Eastern Shore is famous for its seafood, history, nature and fresh produce! Come Visit!

Aug 21 – 28

G$30,822 GYD 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 12 – 19

G$82,195 GYD 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.

Mar 17 – 24

G$49,987 GYD 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

G$47,221 GYD per night

Guest favorite

Home in Lexington Park

4.96 out of 5 average rating, 140 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.

Jun 13 – 20

G$104,886 GYD 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.

Oct 12 – 19

G$44,918 GYD per night

Superhost

Home in Cambridge

4.89 out of 5 average rating, 111 reviews

Dorothy's Chesapeake Delight

810 Seabreeze Rd is a quiet cozy retreat located on Brooks Creek off the little Choptank river directly across from the ragged point county boat ramp and dock. Guests are welcome to bring their boat. The house's private dock is just a quarter mile from the public marina. This house is the perfect place for boating, kayaking, paddle boarding, fishing, swimming, crabbing or just relaxing watching the sunset over the historic little Choptank river.

Oct 19 – 26

G$30,948 GYD per night