
House vacation rentals in Dorchester County
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Top-rated house rentals in Dorchester County
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Popular amenities for Dorchester County house rentals
House rentals with a pool

Family Retreat - Private Pool, 4 Bedroom, Fire Pit
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!

Waterfront Paradise with a Private Pool
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.

Gorgeous, waterfront home - Perfect for Families.
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!

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
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!

Spacious and private waterfront, sleeps 10
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.

Luxury Waterfront Home with Private Pool and Pier
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!

Relax by the Water - Summer Dates Available!
Absolutely beautiful home! highly recommend!

Serenity Bay-Relaxing, Spacious House-Private Pool
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

Spacious Lakefront Cottage w/ Private Pier
Awesome place and looked like the pictures. Crabbing was easy and kayaks were a lot of fun. Don’t use the elevator

Rumbley Retreat
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!

Waterfront with sweeping bay view & private beach
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.

Our Bay House-Your Home Away from Home!
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!

Waterfront home with three bedrooms,3 full baths
Perfect weekend away! The home backed up to the Chesapeake Bay. The home was very relaxing. Would definitely stay again!

Great Historic Cambridge Home With Parking!
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!

Stewart Ave Retreat
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!

20% off for Upgraded Bay Oasis in Scotland, MD!
Tricia is amazing and was very helpful during our stay.
Private house rentals

Secluded River Front Cottage
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.

Tranquility on Talbot
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!

Beachfront Chesapeake Bay Retreat
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.

You'll enjoy the The Great Escape in Cambridge!
Beautiful home. Great location. I have enjoyed getting to know Cambridge better. Highly recommend.

• Peaceful Point • A relaxing waterfront retreat
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!

House of the Setting Sun/Deal Island Bayfront Home
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.

18-Acre Waterfront Sanctuary: Peace & Privacy
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.

Hoopers Island Victorian with 360 Water Views
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
- Rentals with a kayak Dorchester County
- Rentals with breakfast Dorchester County
- Kid-friendly rentals Dorchester County
- Rentals with pools Dorchester County
- Pet-friendly rentals Dorchester County
- Rentals with a hot tub Dorchester County
- Rentals with a patio Dorchester County
- Rentals with a fireplace Dorchester County
- Rentals with beach access Dorchester County
- Waterfront rentals Dorchester County
- Rentals with outdoor seating Dorchester County
- Rentals with a fire pit Dorchester County
- Apartment rentals 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
- Ragged Point Beach
- Quiet Waters Dog Beach
- Severn Beach
- Sparrows Beach
- Guard Shore
- Langford Sand
- Saint Jerome Beach
- Plantation Lakes Golf and Country Club
- Matapeake Clubhouse and Beach
- Flounder Pavilion Beach Front - Sandy Point State Park
- Lane Beach
- Piney Point Beach
- Brownies Beach
- Chesapeake Beach Water Park
- Lake Presidential Golf Club
- Rose Haven Memorial Park
- Triton Beach