Pet-friendly holiday rentals in Southern Maryland

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!

We stayed at Trevor’s Air B&B to support my boyfriend in an Ironman 70.3 and couldn’t have been more happy with the proximity to the event. We greatly appreciate Trevor’s kindness, responsiveness and accommodations. Would absolutely recommend this place!

This was a great place to stay for a girl's weekend. We each had plenty of space, beds and bathrooms. The pictures don't quite do this place justice. The views of the water are so peaceful. We enjoyed the screened porch for coffee and happy hour. The kitchen is fully stocked and the decor and furnishings are just so cute! Leonardtown is a short drive for boutique shopping and cute cafes. There wasn't really a great place to swim and lounge by the water, but we still really enjoyed our stay. Would highly recommend!!

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

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!

Great stay! No issues and excellent communication. Close to downtown. Very responsive and had all kinds of amenities. I would stay 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.

Quiet location at the end of the street. The fenced-in yard is great for pets. The house has an interesting layout making the primary bedroom feel separate and private from the rest of the house.

It was a great and very calm place to stay!

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 LOVED the space! We’ve been working on downsizing and the layout and hidden storage areas were exactly what we want in our future home. It was so, so comfortable. So much so that we never did use the hot tub that we really wanted to use 😂 We enjoyed the space and just vegged. We were doing Safety Patrol for the Bay Bridge Swim and there was plenty of room for our jet skis & double trailer. Wonderful hosts. Even joined us on the pool deck (upon invitation) for some friendly conversation. Cinnamon the golden was a sweetie too. Wonderful experience. Don’t hesitate to book. You won’t be sorry.

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, relaxing stay at Annie’s place. She was very attentive and friendly! The space was cute and had a pretty view of the marina - where the tiki bar and pool are located. Everyone was so friendly in town and made us feel welcome. Check out the little museum and walk around the neighborhood- it’s delightful!!

Had a great time at The Hive! The 70s, Retro feel was spot on (including period LPs and a record player), but with the modern amenities you'd expect. While we didn't take advantage of the community center pool, it was close by and looked well-kept. The local beach areas on the lower Potomac are a quick drive/bike ride away and had just enough beach space and swimming areas (though no amenities, so keep that in mind). A great hideaway that we'd love to visit again and stay longer at!

Enjoyable stay! Wonderful bed! Excellent communication throughout. Thank you.

Enhanced up-to-date old school Chesapeake Bay waterfront vacation. Serene beautiful surroundings, fishing, crabbing, lounging, birding, napping on large screened in porch. Coffee on porch in morning watching crabbers work their lines. Osprey, Mallards, Brown Thrashers, Blue Birds, Bald eagles, Mocking birds, and a Whip-poor-will. Great for walking my dog, friendly neighbors. Fantastic sunsets, nearby wedding venues, comfortable beds, good air-conditioning. Everything worked and was clean. Good for families, girlfriend get aways, and a welcome break from the hustle and bustle of a busy life. Loved the fenced in yard, wished we had time to use the firepit, picnic table, TV/Mancave/Movie room and Tiki Bar! Hope to come back again. Thank you Matt and Jenn

We returned to this gorgeous home for a second time this summer for a full week’s stay. Not only is the home, landscaping and views beautiful, the house is well equipped with everything we needed for a very comfortable stay, especially the kitchen. We enjoyed finding shark teeth on the private beach, relaxing in the hammock and taking drives into town which is just a short trip away. Nicholas was a super helpful and responsive host. Thank you for your hospitality and sharing your beautiful home! We’ll be back next year!

We had such a nice visit! Ryan was very responsive to questions and requests. The house is very cute and perfect for a family with kids. Lots of toys and games and outdoor equipment - and a fun tree swing! The little sandy area was just right for our three kids (ages 1, 4 and 7). We ate all our meals outside on the deck overlooking the water. The neighbors were very friendly. Everything was great!

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

Beautiful Home which provided for a great week of relaxing for me and my family. Access to water was amazing.

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

it was an amazing place to say the least. Very elegant and homey at the same time. lots to do without ever leaving the house, but not far from the beach so there was so much to do. Highly recommend these folks.

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!