House vacation rentals in Dorchester County

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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 stars4 days 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 stars1 week 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, 16 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

DeniseRating, 5 stars7 months ago
The area and view are beautiful and the home's decor is welcoming. The home was very comfortable for our family group and had a VERY well-stocked kitchen. The master bed was VERY comfortable as were the rest of the beds. My husband and I slept well. We all felt at home. MJ was very responsive when I had questions and communicated about the property in clear, concise language. The host provided many outdoor recreation opportunities, which included paddleboards, kayaks, and life jackets. There was a nice sized pool but we were visiting out of season so we did not use it. The exercise room downstairs has a lot of equipment. We all enjoyed our time together. Our family is asking to come back again next year. Thanks for a great stay!
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, 16 reviews

Peaceful Waterfront Home with Pool and Pier

TaylorRating, 5 stars1 week ago
The location looked exactly like the photos and the home was kept in great shape! The neighborhood was very quiet and peaceful with friendly neighbors! Overall, all amenities that were included with the stay were amazing. Mindy was also super responsive making our travel arrangements less stressful!
Guest favorite
Home in Fishing Creek
4.95 out of 5 average rating, 41 reviews

Bay Front Villa on Chesapeake

PatrickRating, 5 stars2 weeks ago
Great host who was very responsive. Very nice house, clean, with beautiful views. Lots of space and things to do on sight. Perfect for a peacful private get away
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 stars2 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 stars3 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
A spacious living area features a comfortable brown sofa and plush chairs arranged around a coffee table. A modern electric fireplace is mounted on a white-paneled wall, while large windows provide natural light and views of the outdoor landscape.
Home in Scotland
4.89 out of 5 average rating, 19 reviews

Secluded River Front Cottage

MattRating, 5 stars1 week ago
Everything was great. Our family had a wonderful time at this spectacular location!
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 stars5 days 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!
Guest favorite
A serene river view showcases a vibrant sunset, with hues of orange and purple reflected on the water's surface. The calm landscape is framed by gentle grasses and shrubs, providing a tranquil backdrop to the distant shoreline.
Home in Lexington Park
5 out of 5 average rating, 9 reviews

Stunning Views, Remodeled Family-Friendly Home

TammiRating, 5 stars1 day ago
This was a truly lovely and clean home. Staying there was so wonderful - sitting on the screened porch listening to the water, walking the waterfront, lovely. It was so peaceful and calming of a location. Also, walking or biking distance to the St. Marys college and historical park. I recommend anyone stay there - I would again. We felt so comfortable and welcomed into this gorgeous waterfront property. You cannot beat the views and location. Communicative hosts. Thanks for a great stay!
Guest favorite
The exterior of a multi-level home features a stone facade with large rectangular windows, allowing natural light to enter. A garage door is prominently displayed, and a front entryway is equipped with a glass door. Small landscaping is visible along the pathway.
Home in Cambridge
4.91 out of 5 average rating, 22 reviews

Casa Maria heart of downtown.

Aaron JRating, 5 stars1 week ago
I had a great stay! The place was clean, comfortable, and had everything I needed. I was in town for the Eagaman 70.3 Triathlon, and it was the perfect spot to relax before and after the race. Super easy check-in and a nice, quiet area. Would definitely stay here again.
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 stars2 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 stars1 week 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!

Private house rentals

Top guest favorite
The house exterior features light-colored siding with dark green shutters framing the windows. A clean walkway leads to the entrance, surrounded by freshly mulched flower beds. Tall trees and shrubs enhance the quiet neighborhood setting.
Home in Cambridge
4.99 out of 5 average rating, 91 reviews

Tranquility on Talbot

JessicaRating, 5 stars1 month ago
Mary Beth was an amazing host. She made this vacation extremely stress free! The house was gorgeous, and the location is so peaceful! Mary made wonderful suggestions on places to eat and things to do! She was so accommodating and made this so easy! We will definitely be back to tranquility on talbot! ☺️
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.
Top guest favorite
A bright dining area is located near a staircase, featuring a large table surrounded by black chairs. Natural light enters through nearby windows, illuminating the hardwood floors. An art piece hangs on the wall, complementing the space's neutral tones and inviting atmosphere.
Home in Cambridge
4.96 out of 5 average rating, 26 reviews

Spacious Historic Craftsman only 3 blocks to water

KennedyRating, 5 stars1 week ago
This was great for our stay in town for the Ironman 70.3! Walkable to the race venue and a great neighborhood.
Superhost
An aerial view captures the farmhouse nestled among lush greenery beside a winding waterway, with the bay visible in the background. The property is bordered by open spaces and pathways, enhancing its serene natural setting.
Home in Madison
4.91 out of 5 average rating, 32 reviews

Farmhouse by the bay! Beach and pier access.

ErinRating, 5 stars8 months ago
We had a lovely stay at Patrick’s place! It had everything we needed for a long weekend on the shore. A very comfortable home. Patrick was extremely responsive and helpful, with easy check in and check out. The kitchen was particularly lovely and well appointed! The house number is a little small so keep an eye out. And the mosquitos were fierce - don’t forget bug spray! Thanks, Patrick!
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!!
Superhost
A spacious living area showcases high ceilings with exposed wooden beams. Large windows allow natural light to fill the room, highlighting a cozy seating area with a sofa and armchairs. A dining table is surrounded by black leather chairs, enhancing the inviting atmosphere.
Home in Church Creek
4.75 out of 5 average rating, 8 reviews

Blackwater Refuge Lodge

NathanRating, 5 stars1 week ago
Glen's place was a perfect retreat for our large group. Access to the water for kayaks and paddle boards, close enough to the small town of Cambridge to easily get there, great wildlife refuge within minutes with great walking and bike trails. Couldn't beat the location. We already want to make plans to come back if they will have us. We encountered a small problem when we checked in, but Julia and Glen addressed it immediately and went out of their way to provide a solution for our group. Julia was a great host and always responsive. We would definitely stay here again. Highly recommended!
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 stars3 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!
Guest favorite
A welcoming living area features a brown leather sofa centered on a wooden coffee table, adorned with flowers. A green front door is visible on the left, leading to an entryway. Adjacent dining space can be seen through an archway, with a chandelier above a dining table.
Home in Cambridge
4.86 out of 5 average rating, 50 reviews

Talbot Corner: Dog-Friendly 3-Bedroom Home

JacquelineRating, 5 stars2 weeks ago
The home is beautiful and well kept. l really enjoyed my visit there.

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