
Waterfront holiday rentals in Dorchester County
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Dorchester County
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
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Popular amenities for waterfront rentals in Dorchester County
Waterfront apartment rentals
Top guest favourite

Private room in Cambridge
5 out of 5 average rating, 22 reviewsWaterfront Room at Happy Campers
RichardRating, 5 stars2 weeks ago
If you want to get away from everything this is the place. There are things to do if you don’t mind driving.
Top guest favourite

Flat in Cambridge
4.96 out of 5 average rating, 27 reviewsHappy Campers Waterfront Suite
ZackRating, 5 stars1 week ago
We were on the eastern shore for a quick weekend trip to do some hiking in the area. We spotted Brad’s place and the location looked quite appealing. It was even more than we expected - quiet, serene, and right on the water. The space was clean and cozy, exactly enough space for the two of us, and we had ample room to enjoy the outdoors. If only the weather had been a little more cooperative - the wind off the bay can be quite something! We enjoyed sitting in the cozy warmth and watching out the windows - we even ventured onto the deck for a bit, despite the wind. The fresh-baked cookies were an extra plus. This is also a great spot for birdwatching!
Guest favourite

Private room in Cambridge
5 out of 5 average rating, 20 reviewsFarm View Room at Happy Campers
AnnaRating, 5 stars3 weeks ago
Cute and clean place, with comfy beds , nice shower and lots of little thoughtful touches that make one feel welcomed. The location is very peaceful and beautiful. The hosts are most kind and accommodating. We only stayed one night but hope to be back for a few days when the weather is warmer to spend time on the water.
Waterfront house rentals
Guest favourite

Home in Woolford
4.93 out of 5 average rating, 145 reviewsWaterfront Getaway with Dock
CassandraRating, 5 stars1 week ago
Perfect for a weekend getaway! Sitting on the dock listening to the birds in the evening, and again in the morning with my coffee was so relaxing. Peaceful, private, and comfortable. The house had everything I needed. Chickens were a fun bonus. Can’t wait to come back again!
Guest favourite

Home in Ridge
4.89 out of 5 average rating, 56 reviewsWaterfront Paradise with a Private Pool
KathyRating, 5 stars4 months ago
It was absolutely wonderful staying at Joanne's home. It was very comfortable and loved the outdoor firepit. Very peaceful and lovely home. We would love to come back again for another visit.
Guest favourite

Home in Lusby
4.96 out of 5 average rating, 142 reviewsCoastal Oasis On The Chesapeake, King Bd sleeps 12
MarceloRating, 5 stars2 weeks ago
This beautiful Lusby home was everything we hoped for and more. The views of the Chesapeake Bay are absolutely stunning—sunrises and sunsets were unforgettable. The house is spotless, stylish, and super comfortable, with thoughtful touches throughout. We loved relaxing on the deck, watching the water and wildlife, and enjoying peaceful evenings by the fire pit. It’s the perfect escape—private, serene, and just a short drive from charming local spots. Can’t wait to return!
Guest favourite

Home in Cambridge
4.96 out of 5 average rating, 112 reviewsGorgeous, waterfront home - Perfect for Families.
Leslie RogersRating, 5 stars5 months ago
We had the most beautiful Thanksgiving gathering at Casey’s Porch on the bay for an extended family reunion. The house is lovely - spacious, gorgeous and cozy at the same time. The views on the water were amazing. There were plenty of beds and ‘hang out’ spots for our tweens and teens, and 3 private baths for the adult couples were much appreciated. And our hosts could not have been more helpful and friendly. Thank you for giving us this opportunity to make more happy memories together!
Guest favourite

Home in Lusby
4.92 out of 5 average rating, 79 reviewsSpacious and private waterfront, sleeps 10
MichaelRating, 5 stars1 month ago
The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.
Top guest favourite

Home in Cambridge
5 out of 5 average rating, 34 reviewsSerene getaway with great waterfront views!
EugeniaRating, 5 stars7 months ago
We recently had a wonderful stay at Travis's place, and we couldn't have felt more at home. The house is not only beautiful but also comfortable, making it the perfect retreat. It’s one of the best-stocked homes I’ve encountered on Airbnb, which made our stay even more enjoyable. Travis was a wonderful host, always responsive and ready to assist with any questions. I truly hope to return in the future. Thank you, Travis, for hosting us in your lovely home!
Top guest favourite

Home in Cambridge
4.98 out of 5 average rating, 48 reviewsWaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse
KatieRating, 5 stars1 week ago
We were so impressed with the property, amenities and host communications. The house was spotless, comfortable and packed with everything you could think of and MORE! Kitchen and bathroom were fully stocked, sunscreen, bug spray, books, games, even a karaoke machine!! The hot tub was amazing, with a stunning waterfront background. I wish we had stayed longer to enjoy the fire pit, paddle boards, kayaks and private pier. definitely adding this to our list of favorite homes. fabulous host was the cherry on top! We mentioned we were celebrating birthdays and were surprised with wine, chocolate and a note wishing happy birthday.
Guest favourite

Home in Lusby
4.92 out of 5 average rating, 13 reviewsRiverview Retreat
JonRating, 5 stars4 months ago
The house was perfect for our family get-away. There is enough room for everyone and yet the large public space made it easy to congregate. The kitchen is amazing for the cooking a meal and there was a great selection of movies when we came back tired and wanted to unwind. It was quite cold out but the house was warm and cosy and we enjoyed our time hanging out there.
Destinations to explore
- Rentals with pools Dorchester County
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- Sandy Point State Park
- Six Flags America
- Heritage Shores
- Maryland Renaissance Festival
- Gerry Boyle Park
- Idlewilde Restoration Project
- Quiet Waters Park
- Guard Shore
- Ragged Point Beach
- Quiet Waters Dog Beach
- Sparrows Beach
- Matapeake Clubhouse and Beach
- Saint Jerome Beach
- Plantation Lakes Golf and Country Club
- Langford Sand
- Severn Beach
- Flounder Pavilion Beach Front - Sandy Point State Park
- Lake Presidential Golf Club
- Piney Point Beach
- Lane Beach
- Brownies Beach
- Chesapeake Beach Water Park
- Rose Haven Memorial Park
- Triton Beach