Family-friendly vacation rentals in Shady Side

This was a very great find. Affordable for the part of the city we were in. Lots of energy and activity around the area, with plenty of places to eat/drink within a few block radius. Close to everything you need to be close to downtown. Easy check-in process. Beautiful, clean apartment. All in all, a wonderful spot to stay.

Overall a great place. It's only a short 10-15 minute walk on sidewalks to the rest of Eastport and the Annapolis harbor area, but in a quiet neighborhood that isn't busy with vehicle or foot traffic so it was easy to enjoy the lovely garden and patio outside with minimal city noise. It is accurate as described and from the photos. Did not experience any problems in the neighborhood or feel unsafe.

This home was the perfect place to celebrate my daughter’s graduation! We had family travel in from several states, and everyone felt comfortable and truly enjoyed the spacious layout. It was a bit too chilly to use the pool, but I’m already looking forward to booking this home again. I’ll definitely be a repeat renter!

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

Super nice place. Probably the most well stocked place we’ve stayed at. Walkable to everything and still in a quiet location. Bathroom was spacious and clean! Hot tub in the courtyard was a nice touch. Parking was a little short to come by but we always found a spot on Baltimore St right next to Patterson Park. Charmed Coffee was a great place for coffee and breakfast…dog friendly! 10/10.

Beautiful home and a beautiful location. It was a relaxing environment with very accommodating host. Felt comfortable and would stay again.

Very nice place to stay near Gaylord convention center. Super clean condo. All the essentials are there. Lots to do at the resort as well as nearby walking distance. Having a baby in the group we did quite a bit of laundry. A laundry room was on our floor with two washers and four dryers and free of charge. We barely passed anyone on the seventh floor. We would def stay here again.

This place is awesome!!! Very quiet and nice neighborhood. This was the place that I chose for our 11 th wedding anniversary and could not ask for a better experience. The kitchen is what I loved the most . Many places to eat near by and the Chesapeake bay is right there.

Great place in a cute area!

Perfect location if you’re in Annapolis for a game or just to visit the city. Christopher’s house was the perfect location and distance from everything in the city. Also, very spacious and nice house perfect for me and my 4 other friends.

It was a very nice place. We had a great time.

Rick's place was perfect -- convenient, clean, cozy, and comfortable. We will rent it again!

We can’t say enough good things about Megan’s place. Our favorite part was how well-appointed the kitchen is, but it’s all great. Very walkable/bikeable city, so you can leave your car behind.

awesome place im looking to return in a few weeks hopefully I could book again. amazing spot.

Everything was great. Love the fact that it was only a 10min drive to the pool where my water polo tournament was held. I got lucky almost every night with parking, which was in front. One day I had to park around the corner but it wasn’t a far walk at all. They gave me places to eat and drink which worked out when I met an HS friend. Communication was great. Every other day or so they would check on me to see if I needed something, not in person but through messages. Which was great. Tv was loaded with apps, all you needed was you sign in info. Will totally rent from them again.

Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.

Absolutely loved this space. The location is great and allows for exploration of the city. The space itself was clean and spacious. My favorite piece was having access to the gym within the Fairmount hotel (if im not mistaken). Lastly, host(s) are extremely responsiveness. I had questions about the property prior to booking as i was booking extremely last minute and I received a quick response.

Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

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.

Nathan has a lovely home—it feels like stepping back in time into one of old Washington’s charming houses. Everything was spotless and well-maintained, and communication with Nathan was excellent. The location is convenient, about a 25-minute walk to Capitol Hill. While the surrounding area could be better—the streets were a bit dirty—it wasn’t a big deal and didn’t affect our overall experience. We had a wonderful time in Washington, and staying at this house was definitely part of it. Thank you, Nathan!

Martha's place is a lovely retreat. There is enough privacy between the main house and the guest house. The guest house is spacious and comfortable with a great screened in porch and access to the pool. It's in a quiet and peaceful area. I look forward to coming back again.

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!

Always love staying there. now that my daughter will be moving, they have set the bar high for anything we find in Alabama!

I recently hosted my wedding at Rousby Hall, and it was truly the most unforgettable experience. The grounds are absolutely stunning — from the waterfront views to the beautifully maintained gardens, every corner felt like a dream. The historic home itself is full of charm and elegance, offering the perfect backdrop for both our ceremony and celebration. Polly, the host, went above and beyond throughout the entire process. She was incredibly helpful, kind, and responsive, which made planning feel effortless. Her knowledge of the property and attention to detail ensured everything went smoothly. I can’t imagine a more perfect venue or a better person to work with. Rousby Hall gave us memories that will last a lifetime, and we’re already talking about returning for future celebrations. If you’re considering this venue — do it! You will not regret it.