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House vacation rentals in Dorchester County

Find and book unique houses on Airbnb

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Popular amenities for Dorchester County house rentals

House rentals with a pool

Top guest favorite
A sparkling pool is surrounded by a paved deck and wooden fence. Comfortable loungers are positioned at the poolside, and colorful umbrellas provide shade. Lush trees form a natural backdrop, enhancing the serene environment.
Home in Bivalve
5 out of 5 average rating, 21 reviews

Family Retreat - Private Pool, 4 Bedroom, Fire Pit

AshleyRating, 5 stars1 week ago
Where do I start? My boyfriend and I randomly chose Ann’s place for a quick weekend getaway knowing nothing about the town or Bivalve. It was such a great trip! Very quiet little town with the nicest locals! Ann and Eddie came by and took us in the golf cart and sharing a little about the town. Ann’s space was PERFECT and CLEAN! So peaceful and relaxing. Having the pool was great for the few hot days we had. Absolutely loved and recommend visiting this quaint little town and staying at Ann’s if you get the chance!
Guest favorite
Aerial view of a home with a fenced swimming pool, surrounded by lush green grass. The pool features a clear blue water, and several lounge chairs are positioned around its edge. Steps lead from the house to the outdoor area, enhancing accessibility to the pool.
Home in Ridge
4.9 out of 5 average rating, 58 reviews

Waterfront Paradise with a Private Pool

BrittanyRating, 5 stars2 weeks ago
Such an amazing place! Joanne was super responsive and flexible. The views were unmatched! Perfect Mommy and Daddy getaway and we will certainly be back with the kids!
Guest favorite
A private salt-water pool is featured, surrounded by lush greenery. The pool's shimmering blue water reflects the sunlight, while a smooth entry step leads into the inviting space. A safety fence encloses the area, ensuring guest privacy.
Home in Lusby
4.91 out of 5 average rating, 81 reviews

Spacious and private waterfront, sleeps 10

MichaelRating, 5 stars2 months 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 favorite
A tranquil view of the private pool framed by potted plants featuring colorful flowers. The pool area extends towards a serene body of water, surrounded by trees. The distant shore is visible, enhancing the natural beauty of the setting.
Home in Lusby
5 out of 5 average rating, 19 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

AlanRating, 5 stars5 days ago
Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!
Top guest favorite
The exterior of a stately, refined home displays a combination of light-toned shingles and brick accents. Landscaping includes vibrant flowering plants and manicured greenery, while a brick pathway leads to the welcoming front porch sheltered by a gable roof.
Home in Cambridge
5 out of 5 average rating, 16 reviews

Turtle's Nest - Hist. Cambridge

CoreyRating, 5 stars2 weeks ago
David and Wendy’s home was the perfect place for our family participating in and supporting the Cambridge Ironman with an easy walk to the course and to the Main Street. They went above and beyond accommodating our requests, since we were traveling with a two month old and a two year old. We were very comfortable and loved our evenings in the screened in porch and pool. We would love to stay at David and Wendy’s again.
Top guest favorite
An aerial view of a spacious home surrounded by a green lawn, featuring a fenced pool area with multiple lounge chairs arranged around the pool. The home’s modern exterior is complemented by sliding glass doors that invite outdoor access.
Home in Cambridge
4.94 out of 5 average rating, 17 reviews

Peaceful Waterfront Home with Pool and Pier

KarenRating, 5 stars2 days ago
Our favorite Airbnb stay! Every aspect of this house was well executed & thoughtful. Fantastic layout of the house allowed our family to be as connected as we wanted yet had private places to retreat. The pool was perfect and the dock had everything you could ask for with fishing and crabbing. The kitchen was stocked with anything you would possibly need. Very quiet and calm location, yet near to grocery and restaurants. We couldn’t have asked for a better vacation spot. Mindy was awesome and available for any questions that we had. We are so grateful for this great family vacation spot!
Guest favorite
An inground pool is visible, featuring clear blue water gently reflecting sunlight. Lounge chairs are positioned along the pool's edge, with a tree-lined backdrop providing shade. A person swims in the deep end, while another relaxes on the side, enjoying the environment.
Home in Lexington Park
4.93 out of 5 average rating, 86 reviews

Serenity Bay-Priv Pool-ask about 2-night stays!

JosephRating, 5 stars2 weeks ago
A really great place! Beautiful, peaceful surroundings. House was perfect for a family getaway. Kitchen was well stocked. Room layout allowed for togetherness and privacy. The fire pit was super nice and the lake was great for the kids. Highly recommend!
Guest favorite
An inground pool is surrounded by a concrete deck, with a bright blue surface reflecting sunlight. Lounge chairs are positioned nearby, and a covered porch is visible in the background, providing a space for relaxation. Lush green lawns frame the pool area.
Home in Cambridge
5 out of 5 average rating, 12 reviews

"Goose Landing" Waterfront Retreat

AlexandraRating, 5 stars5 days ago
It is NOT possible to find something negative to say about this property. Absolutely wonderful! Hubby and I went for a week to celebrate his retirement and Father’s Day. I really just wanted some peace and quiet from the chaos of the renovation influencers who recently moved in next to our home. Lol. This property has PEACE in spades! You’ll feel like the only people on earth. Yet nice restaurants and shopping are just down the road. The setting is beautiful. We spent much of our time on the screened in porch watching the abundant wildlife. We swam, canoed, explored and just relaxed. The house itself is amazing. So comfortable with tons of seating for everyone. The gorgeous kitchen has everything you’d need, and there’s an appliance closet filled with goodies. You have TWO Keurigs, Doug! Lol. Super comfy beds, awesome showers. You will not be disappointed. We hated leaving and will be back! Doug is super responsive, and couldn’t be nicer. You will not regret choosing this home ❤️

Weekly house rentals

Guest favorite
A welcoming front porch showcases a hanging chair and an American flag, with neatly trimmed landscaping featuring dark mulch and green plants. The blue exterior of the house complements the inviting atmosphere, and a pathway leads to the front door.
Home in Cambridge
5 out of 5 average rating, 22 reviews

Aurora Blue - A stylish experience

JanetRating, 5 stars4 weeks ago
Aurora Blue is stunning, no detail was left out of the planning. The space is well planned to allow privacy and quiet when resting. Each room has a en suite bathroom and the master suite is beyond 5 star. The home was immaculate, having coffee and paper products available was an extra bonus. Great patio for sitting outside and quiet at night without any disturbances. We locked ourselves out and the host came onsite quickly to address the problem we created. Excited to go back one day.
Guest favorite
Two dark grey Adirondack chairs are positioned on a sandy beach, set against a backdrop of tall grasses and distant beachfront houses. The scene conveys a calm coastal atmosphere, inviting relaxation and beachside conversation.
Home in Lusby
4.89 out of 5 average rating, 65 reviews

Beachfront Oasis with Amazing Views

NguyetRating, 5 stars1 month ago
We had such a wonderful stay! The kitchen was incredibly well stocked—honestly better than my own at home—with 5-6 large pots, an Instant Pot, every spice you could think of,peelers (which saved me!), and both a NutriBullet and a regular blender. It made cooking for the family a breeze. The kid had a blast on the trampoline, and we all loved the easy beach access with calm waters perfect for swimming all day and kayaking. The beach was also perfect for a peaceful morning run, and at night we could see the lighthouse light on the water. The porch quickly became our favorite spot—we gathered there to watch a rainstorm and were treated to a stunning double rainbow. The sky was full of stars at night, creating such a peaceful atmosphere. The grill on the porch made cooking super convenient. We enjoyed being close to a large park where we played pickleball. The beds were large and comfortable—everyone slept really well. Michael was a fantastic host—very attentive and accommodating.
Guest favorite
The exterior showcases a three-story home with a gabled roof, surrounded by large trees providing shade. A welcoming front porch is situated under the expansive porch roof, while a white picket fence encloses the grassy yard. A path leads from the sidewalk to the porch steps.
Home in Cambridge
4.98 out of 5 average rating, 53 reviews

You'll enjoy the The Great Escape in Cambridge!

IngridRating, 5 stars3 weeks ago
Clare was super responsive, and got right back to me with recommendations for restaurants and answering any questions. The home was great for our party and we were able to walk downtown to restaurants and shops. Beds and pillows were very comfortable. Overall a great stay!
Guest favorite
A spacious front porch features wicker furniture arranged for relaxation. Ceiling fans are mounted above, and sunlight filters through the open space, casting light on a green lawn visible beyond the railing.
Home in Cambridge
4.95 out of 5 average rating, 44 reviews

Hambrooks House - Porched Sanctuary near Choptank

NakeyaRating, 5 stars2 months ago
Loved my stay beautiful home with serene surroundings and lots of local historic attractions. Highly recommend James’ place!
Top guest favorite
A wooden pier extends over gentle waters, surrounded by rocks. The scene is illuminated by a soft pink and orange sky at sunset, reflecting on the water's surface. Additional pilings can be seen in the distance, enhancing the tranquil setting.
Home in Cambridge
5 out of 5 average rating, 34 reviews

• Peaceful Point • A relaxing waterfront retreat

KacieRating, 5 stars2 weeks ago
Peaceful point was stunningly beautiful! A perfect place for adults and kids to unwind and enjoy the scenic views and beautiful nature. Joanna was the best host and surprised us with a little welcome package with a kind welcome card and some of our favorite treats from Trader Joe’s! She was so helpful and responsive via text. Can’t thank her enough!
Top guest favorite
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
4.98 out of 5 average rating, 53 reviews

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse

AnilRating, 5 stars2 days ago
Our stay was wonderful. The house was clean, had beautiful views from the bedrooms, and was the perfect place to relax. The kitchen was fully stocked (e.g. ketchup, mustard, coffee pods), and a lot of appliances. The air fryer came in very handy. The outdoor space was truly amazing. The screened porch was great for reading, evening meals, and relaxing. Being on the bay meant lots of water fun on kayaks and paddle boards. Our hosts were very thoughtful in the way they prepared the house for guests. Anytime we had a question, they were very quick to respond. I would highly recommend this place to anyone who enjoys nature and quiet peacefulness.
Top guest favorite
A spacious two-tiered deck is visible, featuring a round table surrounded by two chairs and additional lounge seating. Lush greenery and tranquil water views are present in the background, creating a serene outdoor space for relaxation.
Home in Lusby
4.93 out of 5 average rating, 15 reviews

Riverview Retreat

Helena LightRating, 5 stars4 weeks ago
This served as a low key weekend retreat for us. We unplugged and enjoyed being in each other’s company. Being on the river, surrounded by trees and birdwatching was exactly what we needed. The kitchen was well appointed so we were able to enjoy family favorite activities (cooking together and playing board games).
Top guest favorite
A scenic view of a spacious green lawn bordering a tranquil waterway. A white house is positioned near the water's edge, surrounded by trees and a clear blue sky. The peaceful setting is enhanced by the gentle reflection of the landscape in the water.
Home in Oxford
5 out of 5 average rating, 57 reviews

Stunning Chesapeake waterfront home

AlanoudRating, 5 stars3 weeks ago
We had a truly wonderful stay at this beautiful home! The place was spotless and very well maintained, and we felt comfortable from the moment we arrived. There were plenty of activities to enjoy as a family, and we created some unforgettable memories here. The host was incredibly friendly and responded quickly to any questions we had, which made everything even more enjoyable. The surroundings are absolutely stunning, and the sunset views were nothing short of magical. We would love to come back again!

Private house rentals

Guest favorite
The exterior of a historic home is highlighted, featuring a two-story structure with blue siding and a dark front door. Flanking the entrance are two Maryland flags. Lush greenery and flowering trees surround the property, creating a welcoming atmosphere.
Home in Cambridge
4.97 out of 5 average rating, 35 reviews

Water views, w/BBQ, patio, near downtown& beach!

Maria AlyssaRating, 5 stars1 month ago
Perfect for our group for the weekend. Owners are very responsive and accommodating! Cozy and well kept house. Would book again!
Top guest favorite
A firepit surrounded by two black chairs is set on gravel, offering a cozy outdoor space. A wooden pathway leads to the water’s edge, where colorful kayaks are visible along the serene lakeshore, with lush greenery framing the scene.
Home in Lusby
5 out of 5 average rating, 38 reviews

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!
Superhost
The image captures a vibrant sunset over the water, featuring colorful clouds and a serene horizon. Tall grasses border the foreground, enhancing the natural beauty of the waterfront location. Soft rays of light emerge from the clouds, creating a peaceful atmosphere.
Home in Westover
4.94 out of 5 average rating, 82 reviews

Beachfront Chesapeake Bay Retreat

MarvinRating, 5 stars3 weeks ago
I loved it, very comfortable, nice beach and organized, I recommend it
Guest favorite
A private pier extends into the calm waters, framed by silhouetted posts. The sun sets on the horizon, casting soft oranges and yellows across the sky. Outdoor seating is visible in the foreground, providing a perfect spot to enjoy the serene view.
Home in Cambridge
4.88 out of 5 average rating, 52 reviews

Waterfront, amazing views, pier, fishing/crabbing

SandyRating, 5 stars9 months ago
The house are clean, bright with a great view. We had a wonderful time and were lucky to have wonderful weather during our stay! We also had a lot of fun playing Mad Gab and other games in the games chest. We were successful in catching some fish and plenty of crabs. It was a great vacation. We enjoyed it very much.
Guest favorite
Four black Adirondack chairs are arranged on a lush green lawn, facing the calm waters of Chesapeake Bay. Gentle waves reflect the bright blue sky, offering a serene view. Small bushes line the edge of the property, providing a natural border.
Home in Lusby
4.99 out of 5 average rating, 89 reviews

Waterfront with sweeping bay view & private beach

RahinRating, 5 stars4 weeks ago
We recently stayed at Colin’s Airbnb in Lusby, MD, and it was an absolute gem. Nestled right by the ocean, the home was quaint, peaceful, and filled with charm. The views and the serenity of the surroundings made our getaway feel truly special. Colin was a wonderful host—quick to respond, kind, and genuinely pleasant to chat with. When we reached out for local bakery recommendations for our daughter’s birthday cake, he gladly shared a few. We ended up choosing one and couldn’t have been happier—the cake was perfect! The home itself was cozy and comfortable. The IKEA bedding added a clean, modern touch and made for a restful night’s sleep. There was just the right amount of space for the three of us to relax and enjoy our time together. Thank you, Colin, for making our stay memorable—we’d love to return someday!
Superhost
A cozy den showcases a warm seating arrangement featuring a light-colored sectional and an accent chair. A bookshelf filled with books lines one wall, while a television is mounted on another. A coffee table sits in the center on a patterned area rug, illuminated by natural light from nearby windows.
Home in Tilghman Island
4.83 out of 5 average rating, 12 reviews

Charming Summer Cottage – Relax and Unwind Here!

HilaryRating, 5 stars5 months ago
This was the perfect place to stay for a few days of peace and tranquility! The house was beautiful and everything was fresh and clean! The host was incredibly helpful and responsive. Everything was as described in the listing. We loved the quiet of the neighborhood and took a lot of walks. Highly recommend staying here if you are considering a visit to this area!!
Guest favorite
A two-story gray house is depicted with large arched windows and a welcoming front porch. The structure sits on stilts above the water, while a wooden dock extends towards it, surrounded by quiet water and greenery. The sky displays soft evening light.
Home in Scotland
5 out of 5 average rating, 33 reviews

Bay Front Beach House

JenRating, 5 stars3 weeks ago
We booked this place for a weekend getaway with our little ones. It was absolutely the perfect place for what we were planning! The private beach was PERfECT for young children! the kids loved being able to ride their scooters under the house. We got some fishing in, daughter was a spot master! The hammock was lost in a storm before we arrived, but our superhost made sure we could enjoy a hammock!! upon hearing that it was the top of the list of kids wish list, she took time out of her day and drove all the way and installed a new hammock for us!! Was even so considerate to offer to pick up any needed items. I believe more than the kids, my dog had the time of his life!! They even had doggy bowls ready!! We will definitely be back!! This place is awesome!! Thank you Dana for you gracious hospitality!!
Guest favorite
An aerial view captures a serene waterfront retreat surrounded by dense trees and a winding creek. The house is nestled within the lush greenery, providing a sense of seclusion and harmony with nature.
Home in Ridge
4.93 out of 5 average rating, 54 reviews

Private Waterfront Retreat | Chesapeake Sunrise

CatherineRating, 5 stars4 weeks ago
We had a wonderful stay! The location was absolutely beautiful, and my family especially enjoyed having access to the private dock. We used the stand-up paddle boards, kayaks, and canoes every day after giving them a quick clean. The paddle boat didn’t work quite as expected, but we made it work with some oars and still had a great time on the water. The house itself was clean, comfortable, and well-stocked with everything we needed to prepare our own meals. The host also provided excellent local recommendations, which helped us make the most of our trip. Overall, it was a fantastic getaway, and I would definitely recommend this Airbnb to others!

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