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, 18 reviews

Family Retreat - Private Pool, 4 Bedroom, Fire Pit

Justin DRating, 5 stars8 months ago
Wow. The pictures don't do this place justice -- at all. What an extraordinary layout, especially for larger groups who all enjoy a bit of personal space and quiet. There are nooks and spots for everyone and everything, from the awesome pool area to the endless spots to sit and read a book or enjoy some coffee. And Ann! What a gem. She bent over backwards to answer questions and make us feel at home, even providing us with special coffee and food recommendations. I've been using Airbnb for a while now -- and Ann is the #1 host I've ever come across. I mean...she's a joy. Her place, of course, is amazing and you'd be a fool not to stay! 10 Stars!
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
4.89 out of 5 average rating, 56 reviews

Waterfront 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 favorite
A spacious dining area features a wooden table surrounded by white chairs, with sunlight streaming through sliding glass doors that open to a deck. A cozy seating area can be seen in the background, together with views of the surrounding nature.
Home in Cambridge
4.96 out of 5 average rating, 112 reviews

Gorgeous, 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!
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, 15 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

DeniseRating, 5 stars6 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!
Guest favorite
The image captures a serene waterfront scene featuring a wooden dock with rounded posts. A small boat is anchored nearby, surrounded by calm water reflecting a clear blue sky. Red umbrellas provide shade to seating areas on the deck.
Home in Lusby
4.92 out of 5 average rating, 79 reviews

Spacious 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.
Guest favorite
A spacious living area features soft carpeting and light blue walls. A large sectional couch is complemented by a glass coffee table and a small dining table with metal chairs. Natural light enters through multiple windows, enhancing the inviting atmosphere.
Home in Cambridge
4.91 out of 5 average rating, 11 reviews

Luxury Waterfront Home with Private Pool and Pier

KiraRating, 5 stars8 months ago
We had the best time at this house!! Gorgeous view and the pool was perfect. The house had everything we needed and it was very comfortable for our family. We cannot wait to come back next summer!
Guest favorite
Large glass doors offer scenic views of the waterfront and outdoor dining area. A grand piano is positioned beside a cozy seating area, featuring a sectional sofa and a decorative tray. Natural light fills the space, creating a bright and inviting environment.
Home in Tilghman Island
4.97 out of 5 average rating, 30 reviews

Relax by the Water - Summer Dates Available!

RonnieRating, 5 stars3 months ago
Absolutely beautiful home! highly recommend!
Guest favorite
The living room features multiple large windows filling the space with natural light. Comfortable seating includes two patterned armchairs and a gray sofa adorned with orange pillows. A coffee table with decorative items and a side table with a lamp contribute to the cozy ambiance.
Home in Lexington Park
4.93 out of 5 average rating, 83 reviews

Serenity Bay-Relaxing, Spacious House-Private Pool

TaniaRating, 5 stars1 month ago
We thoroughly enjoyed our stay at Serenity Bay! Our host was extremely responsive before and during our visit. This was our third year staying in this home for the Maryland State Swimming Championships. The swimmers and parents enjoyed the comfortable and roomy home.

Weekly house rentals

Superhost
Home in Lusby
4.85 out of 5 average rating, 46 reviews

Spacious Lakefront Cottage w/ Private Pier

KyleRating, 5 stars2 weeks ago
Awesome place and looked like the pictures. Crabbing was easy and kayaks were a lot of fun. Don’t use the elevator
Guest favorite
A serene waterfront view shows multiple boats docked along a structured marina. Calm waters reflect the clear blue sky with scattered clouds. A mix of boats of various sizes is visible, together with piers extending over the water, inviting exploration and relaxation.
Home in Westover
5 out of 5 average rating, 16 reviews

Rumbley Retreat

ChadRating, 5 stars3 months ago
Came down for a duck hunting trip! The place was perfect! Very clean and cozy! Hope the owner was very attentive and quick to respond with any questions! If in the area again I will definitely book again!
Guest favorite
A tranquil outdoor seating area is visible with white patio furniture and striped cushions facing the bay. An umbrella provides shade, while a palm plant adds greenery. The calm water reflects the blue sky and fluffy clouds, creating a serene atmosphere.
Home in Lusby
4.99 out of 5 average rating, 86 reviews

Waterfront with sweeping bay view & private beach

Jose PedroRating, 5 stars1 week ago
Perfect place to rest and unwind for couple days. Lovely house with its very own private beach. Great for family fun. I enjoyed the stunning bay view. Being in front of the ocean and the sea breeze. House was clean and comfy. 2 rooms with ocean view. Ample garden space kiddo played around. The upper part of the house is off limits for private use . Only 1 bathroom but okay we were only 3. Loved walking around and exploring Salomon island parks and restaurants. Highly recommend the ruddy duck great food and friendly atmosphere and the island hideaway at Solomon’s. The house water had a sulphur smell making it unpleasant to shower / brush our teeth. Colin was great and communicative the whole time. Loved using one of the kayaks to paddle around the bay. Overall great stay and would come back easily loved the view.
Top guest favorite
A modern kitchen features a granite countertop and stainless steel appliances, including a microwave and refrigerator. Bar stools are positioned at the counter, complemented by decorative golden accents. Natural light illuminates the space, enhancing the sleek cabinetry and stylish backsplash.
Home in Lusby
4.95 out of 5 average rating, 43 reviews

Our Bay House-Your Home Away from Home!

AdamRating, 5 stars2 months ago
I had a great stay at Edna's! It was a wonderful place to rest after long work days. Edna asked what temperature we wanted the place and we chose 70 degrees. One of the bedrooms got much warmer than that, and one of the bedrooms was much colder than the target temperature. I know the thermostat was new to them, but that is my only small complaint. Everything else was excellent!
Superhost
A spacious living area is featured, showcasing a floral-patterned sofa and a glass coffee table. Decorative elements such as potted plants and an ornate display cabinet with collectibles create a homey environment. Natural light fills the space from large windows, enhancing the warm tones of the decor.
Home in Lusby
4.89 out of 5 average rating, 37 reviews

Waterfront home with three bedrooms,3 full baths

JoyceRating, 5 stars2 weeks ago
Perfect weekend away! The home backed up to the Chesapeake Bay. The home was very relaxing. Would definitely stay again!
Top guest favorite
Home in Cambridge
4.95 out of 5 average rating, 231 reviews

Great Historic Cambridge Home With Parking!

AshleyRating, 5 stars1 month ago
What a gem! My daughters and I loved our week spent here. The home is a true beauty with all the charm of a seaside getaway. All of the amenities truly made it feel like home, and the kitchen is amazing! Everything was streamlined and easy, the host was wonderfully responsive, and the home had such a friendly, warm, relaxing feel to it. It was such a terrific experience through and through, I would highly recommend taking full advantage of this beaut!
Top guest favorite
A two-story, gray wooden house features a welcoming front porch with white railings and two hanging plants. Stairs lead up to the entrance, while a green lawn and a white picket fence are visible in the front yard. The quaint architecture reflects the area’s historic charm.
Home in Oxford
5 out of 5 average rating, 41 reviews

Stewart Ave Retreat

AbbieRating, 5 stars3 weeks ago
Our stay was wonderful. Nanette, was an amazing host and extremely accommodating. The house is beautiful and great for dogs. The town of Oxford is stunning and the locals are very friendly. We definitely would stay here again!
Top guest favorite
A spacious game room showcases a sleek pool table, inviting friendly competition. A comfortable seating area is available, complemented by decorative elements that highlight the 'Bliss on the Bay' theme. Natural light fills the room through large windows, creating an inviting atmosphere.
Home in Scotland
5 out of 5 average rating, 20 reviews

20% off for Upgraded Bay Oasis in Scotland, MD!

MichelleRating, 5 stars3 months ago
Tricia is amazing and was very helpful during our stay.

Private house rentals

Guest favorite
Natural light fills a cozy corner featuring a light blue armchair. Floor-to-ceiling windows offer views of the outdoors, framed by soft gray curtains. A wooden deck is visible beyond the glass, surrounded by green trees and a calming water view.
Home in Scotland
4.88 out of 5 average rating, 17 reviews

Secluded River Front Cottage

LindsayRating, 5 stars4 months ago
We very much enjoyed the views of the river from nearly every room in the house! The furnishings (and linens) are like-new and were perfectly spacious for 4 adults & a baby. We’ll be back for our next remote getaway, we love the peacefulness of the area.
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, 89 reviews

Tranquility on Talbot

ChristopherRating, 5 stars7 months ago
This is my second time staying with Mary Beth at this rental. Both times have been wonderful! She is a great host. Friendly, responsive, knowledgeable with local recommendations for things to do and places to eat. Looking forward to stay again in the future!
Superhost
A colorful house is situated on the waterfront, surrounded by tall grasses. A wooden walkway leads towards the entrance, while clear blue skies and green trees frame the serene setting.
Home in Westover
4.95 out of 5 average rating, 76 reviews

Beachfront Chesapeake Bay Retreat

AngieRating, 5 stars7 months ago
We enjoyed our stay in Maggie & James’s quaint and cozy home. The area was quiet and like something out of a book with all the locals and marina and restaurant. Our teens enjoyed playing board games from their childhood even though there were games there for their age group. We were gifted a beautiful loaf of sourdough bread from our hosts. So very thoughtful! If you plan to stay there be sure to check the weather and high tide schedule due to coastal flooding. You’re between the sound and the marshes and low roads can get covered with water. If you’re arriving at night it can be difficult to see where the road ends and the marshy area begins. We enjoyed our stay and our teens want to return when we can have more time sitting out on the beach by the water which is just a few steps from their home.
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, 49 reviews

You'll enjoy the The Great Escape in Cambridge!

StaceyRating, 5 stars1 month ago
Beautiful home. Great location. I have enjoyed getting to know Cambridge better. Highly recommend.
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, 29 reviews

• Peaceful Point • A relaxing waterfront retreat

DarleneRating, 5 stars4 days ago
This property was wonderful. We were there with another couple. The home was well appointed including a lovely coffee area. Well designed, nicely decorated that was up to date and clean. The view was wonderful. We enjoyed the towns of Cambridge, St Micheals and the Blackwater Preserve.I would definitely come back again!
Guest favorite
A dock extends over calm waters, framed by a vibrant sunset showcasing hues of orange and purple. A picnic table is positioned on the dock, and a flag gently flutters nearby, enhancing the peaceful scene.
Home in Deal Island Historic District
4.93 out of 5 average rating, 29 reviews

House of the Setting Sun/Deal Island Bayfront Home

DianaRating, 5 stars5 months ago
perfect family-friendly retreat. love the secluded area. it was so peaceful and Serene. the layout of the house was such that,even with nine people, there was a secluded place for everyone if needed and a place to gather as well.
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
4.94 out of 5 average rating, 51 reviews

18-Acre Waterfront Sanctuary: Peace & Privacy

JessicaRating, 5 stars2 weeks ago
We wanted a quiet and peaceful getaway, and this place was exactly what we needed. The home was spotless and stocked with everything we needed—and more. One of the highlights for us was taking the kayak out and exploring the cove, which we did multiple times. Chain grocery stores and restaurants are about 25–30 minutes away, but the drive is easy and pleasant, so it feels much shorter. We chose to cook most of our meals at home, and the kitchen had everything we needed. Fred and Gette are some of the best hosts we’ve come across on Airbnb—friendly, responsive, and genuinely helpful. We had a couple of minor issues during our stay, and they resolved them quickly and thoughtfully. They also offered us a late checkout on our last day, which was a huge bonus after a couple rainy days early in the trip. We really appreciated the extra time to enjoy the property. Highly recommend this stay—and any property Fred and Gette host in the future.
Top guest favorite
A spacious, charming Victorian house stands surrounded by lush green grass and trees. The exterior showcases light blue shutters on white siding, with a welcoming porch featuring hanging plants and rocking chairs. The landscape is well-maintained, enhancing the home's inviting presence.
Home in Fishing Creek
5 out of 5 average rating, 14 reviews

Hoopers Island Victorian with 360 Water Views

JanaRating, 5 stars8 months ago
We had a great stay at Kristin’s place! Everything was exactly as described and she left us a nice welcome note and a bottle of wine. Absolutely loved how the living room opened up to the screened in porch. We enjoyed the area and did some fishing, ate at Old Salty’s and got some local crab meat from Rippons. The backyard was perfect for playing cornhole by the fire pit, and we loved watching the hummingbirds on the front porch. Great house and great host. Thanks Kristin!

Destinations to explore