Pet-friendly vacation rentals in Southern Maryland

We loved the experience from booking to check-out. The setting exceeded our expectations. Peaceful and beautiful landscape. Easy to launch kayaks. Chickens were an added bonus. Appreciated the close proximity of Blackwater. Would love to return.

We had a lovely stay! The home is in a beautifully updated old house that still maintains its historic charm. Everything felt clean and thoughtfully cared for. It was peaceful and quiet, with pretty, farm-like views out the windows—great for relaxing. I also appreciated that it was just a quick 10-minute drive to grocery stores, restaurants, and even a 24-hour gym. One big plus for me: there were plenty of towels and pillows, which I always find makes a huge difference in comfort. Would absolutely stay again!

My mom, sisters, friends and I enjoyed a relaxing fun filled time at the Coastal Oasis at the Chesapeake for our Mother's Day Retreat. The view is amazing and truly can be seen from every room in the house! Being able to see the beauty and calmness of the water helped each of us kick back and let the stress melt away. The big dinning room table allowed all of us all to enjoy breakfasts, dinners and touching conversations together. My guests loved the décor and raved about every detail. The beds and furniture were comfortable and house clean. I would definitely come back!

This was our second time staying at Kimberly’s home, and it was just as magical as we remembered. The views of the water are absolutely stunning—whether you’re enjoying your morning coffee or winding down in the evening, it’s hard to look away. The location is perfect: peaceful but just a short walk to shops and restaurants. We also really appreciated the Peloton and treadmill—such a bonus for staying active during our trip. Everything was spotless and thoughtfully prepared. Honestly, we didn’t want to leave. Already looking forward to our next visit!

We had a great stay! The yard was perfect for our dog and playing with our grandson. There was plenty of water and the house met all our needs. The neighborhood was fantastic and we loved taking walks and seeing everyone else out walking their kids and dogs! Definitely will come back!!

Very nice house in a great walkable neighborhood. Host were very helpful and responsive.

Both Dan and Scott could not have been better hosts. This is our 2nd year in a row staying at the Sunnyside Up cottage and we couldn’t have picked a better place. The cottage is quaint and clean. It is fully stocked and has everything you could need for a few nights stay. The communication was excellent and the instructions were very clear for checking in and out. We will definitely return for another stay in the future. The best part about the Sunnyside Up cottage are the views of the river! They are gorgeous!!

Kirk and Diana have a beautiful place! My wife and I enjoyed our stay - it was exactly what we wanted.

It was amazing.The pool is so fun.We had bad weather but we were still a little inside.The location is quiet and beautiful. We will come back for sure. Thank you

Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.

We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.

Cute & spacious boho apartment. My family of 5 was very comfortable inside. Metro & restaurants were close by (5 min or less walk). Free parking pass was great. Currently there is a lot of construction happening in the parking garage and on the street but it wasn’t too loud and once you got used to the few streets that were closed it was easy to drive and walk around the neighborhood.

Thank you Kenny for the hospitality and the coffee! The place was perfect and we had no issues with our stay. We both enjoyed the area and will be back again when Kenny is available of course. Appreciate it!

Immaculate Airbnb, phenomenal location, great value for what it offers. Walkable to so much, 20 min drive to DC, we loved this Airbnb. Thanks to Jomeka for flawless communication. I would recommend this stay.

We had a wonderful time at The Hive! The 70s vibe was like stepping into a time machine. We played records and loved the polaroid camera!

Modern airbnb in a great location. Very walkable and close to restaurants and grocery stores.

It was peaceful and serene. I wanted a place to relax and let the issues of the world fade away. That's exactly what I experienced at Skip-A-Way Landing. The house is not only beautiful but it has a warm and welcoming feel to it. Like coming home after a long time away. Overall the house is lovely however the subtle touches throughout are also much appreciated. It's the small details that let you know that the owners put a lot of thought into it and care about its' guests. I did not want to leave. I'm already looking forward to going back. Highly recommended!

Mari was so responsive and helpful. The house has everything you could possibly need and the beds were so comfortable! Thank you Mari!

We loved out time at this Bayside home. My boys spent outside upon hours at the little private beach, where the water doesn't really get deep for quite a ways and the waves were never very rough. it was perfect for them. we all enjoyed the hot tub, kayaks, comfortable beds. My personal favorite was the hammock right by the water, listening to nothing but the waves and the calls of the ospreys that made the area their home. Forget the overly built up touristy areas and give this place a try. You will not regret it.

Great quiet and secluded place. Very clean and roomy. Nice pond that was good finish with the kids. Definitely going back at some point

Loved the cottage! Quiet, peaceful, and homelike, just what we were looking for. We particularly enjoyed the fishing and crabbing- would definitely return!

Kelly and Thomas were amazing host. Very responsive and accommodating The home was very clean and the location was great.. 10/10. Definitely would book again!

We had a wonderful vacation here. Although it rained during our stay, we found the treehouse to be a great place just for listening the rain drops and having some inner peace.

This place was amazing! Me, my friend and my dog really enjoyed it. It was only a short walk to the beach, the neighborhood was nice and quiet with friendly neighbors and the townhouse was over all great. It was extremely clean, well decorated and had everything you could possibly need. My dog also really loved the back patio area. As well as the place being amazing, the hosts were super friendly and very responsive!