Holiday rentals with outdoor seating in Shady Side

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

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!

This property was very well listed, it was very clean and exceeded expectations. Easy parking and the place feels safe and clean. The hosts are amazing and we are very thankful for their hospitality. 15/10 recommend.

We loved the home. It was everything advertised and more!

Can’t say enough good things about our stay! Beautiful place with everything we could possibly need. The kitchen was well stocked and our host had thought of everything! Clear instructions, great recommendations for local spots etc. And the huge backyard and deck was perfect for us and our pups. Very comfortable beds and pillows too! Finally, host communicated so well and was incredibly accommodating.

The Wise Quack 2 is a cozy, clean Airbnb steps from the Chesapeake Bay, perfect for a relaxing getaway. Sidco’s warm hospitality, comfy beds, and thoughtful touches like the deep tub and hammock make it a gem. The quiet Shady Side location and quick host responses ensure a delightful stay.

Our stay at Justin’s Hot Tub Haven in Annapolis, was exactly that…a haven with a much enjoyed hot tub! Justin was exceedingly responsive, proactive, and flexible. The home is very well appointed with all the necessities, plus all the thoughtful touches like umbrellas, a doggie waste station, and bath robes to name a few. Our children loved the downstairs space (and secretly the adults were thrilled they had it too), and it felt to them like they had their own little apartment. The backyard felt like a small resort. We loved the quick walk to shops and the our boys loved the nearby basketball courts and baseball fields. We highly recommend this home and will stay here again!

This was a great place. It exceeded my expectations. She even had the snacks I like. I could swear it was like she read my mind. Lol. Overall, I enjoyed my stay and would come back.

Peter and Co-hosts were awesome. The place was easy to access, and Peter was proactive in sharing details and was awesome to let us park nearby after check out. Would definitely recommend, and would stay here again when and if returning to DC. The location was tucked away enough to be away from traffic but close enough to access the big sites if you have a car. 10/10 recommend. And he’s right. The most affordable place you’ll find!!

Very responsive host. The side yard is very nice for people with dogs that travel. Location is very nice but DC traffic during rush hour can be rough but this can be planned for. Would stay again.

This space is absolutely stunning. The natural light, the calm atmosphere, and the beautiful design all made it feel like a peaceful retreat. The gas fireplace was my favorite feature. It brought so much warmth and comfort to the space. What really impressed me was how well it is set up for longer stays. Everything was thoughtfully included, from the efficient washer and dryer to the kitchen area, steamer, and other essentials that made my business trip easy. The hosts were kind, attentive, and made everything feel smooth. I felt right at home and definitely recommend this place.

This place was so peaceful. I really felt comfortable and relaxed. It’s a very beautiful area.

Cute and cozy! I felt right at home. Jordan and Danny are very nice folks, the apartment is very well appointed. There is a dock on the property that I should have spent more time on. The bed was a dream to sleep in and I literally overslept my alarm the first day. You will definitely need a car to get around but the apartment is a 3min drive to Safeway, Walgreens, Starbucks, etc. The neighborhood has a homey feel and the apartment has a homey feel which was my jam. My dog had a little accident but I got some carpet cleaner and let Jordan know and she was very understanding. I would definitely stay here again if I am visiting Kent Island.

Driving back from the funeral of a favorite Uncle and dealing with family drama my soul was craving peace, comfort and a respite from everything for a bit. I found that respite in this Air BnB. The river view was blissful and everything was as described, no hassle and no surprises. Here are some things that I hope the reader finds helpful. 1) You can get the keys from the back porch entrance but bring your luggage up thru the carport door or the front don't try to bring your luggage up that spiral staircase. 2) Bring any silverware you may need and a coffee stirrer 3) The device to the side of the bed IS NOT THE AC CONTROL, lol it is the sleep number bed remote. Check that both sides are set to the same setting before getting into bed. Fun fact: Another guest must have thought it would be funny to switch one side on high and the other side on low. The bed sags on one side if you do that. It was so peaceful, I loved it. She couldn't have been more sweet and delightful.

Lynn’s place is fabulously located and well taken care of! I would definitely recommend this place to anyone visiting Bowie, or DC/Baltimore. It’s cost- effective, comfortable and centrally located. We will be back for sure!

We had a wonderful stay at Lauren’s place and would highly recommend to anyone traveling to DC!

Perfect location for exploring Annapolis attractions via walking including Naval Academy and downtown. A bonus for me, all areas were wheelchair accessible (except balcony). Very clean and well maintained! Bed was super comfy!

Chris was a great host making check in and out so easy and flexible! The location of the place was perfect for walking to the market and to get coffee! The space was exactly like the pictures and perfect for a quick getaway with my fiance! Recommend this place!

This was a beautiful condo with plenty of room for everyone to spread out. It was so well stocked with everything you might need- more like staying with a thoughtful friend than at an Airbnb. The area was convenient to the metro yet really quiet for sleeping (even with kiddos who go to bed around eight). The pocket park just a block away was a perfect space for our kids to play. We would definitely stay here again!

very nice place and very well situated. It is clean, decorated with taste (lovely plants) and has everything you need! beds are also very comfortable. I definitely recommend!

Great apartment! Sean’s apartment is very comfortable and tastefully decorated. It is completely quiet at night and the bed is good. There is a good vibe in the neighbourhood and the apartment is less than five minutes from a Green Line metro station that will take you directly to the best art museums in the city. Sean and his co-hosts are very helpful and responsive. I hope to come back to Washington one day and if that happens, I will definitely try to book Sean’s apartment again. Thank you Sean, Megan and Loren for all your helpfulness and a lovely stay!

Israel’s place is a must stay while in DC. I wish I could gate keep it for myself lol. It’s exactly as described in photos. Perfect location in the Navy Yard and walkable to so many places. Each day I was able to walk to Orangetheory and SolidCore to workout and found a cute coffee shop along the way. I think the only thing I disliked was the firmness of the mattress but this will differ for everyone. As a solo female traveler, I felt very safe. Responsiveness, location, cleanliness, check-in, were all on point. Additionally really appreciated Israel’s flexibility as a host. I was supposed to stay in December but due to a last minute emergency I needed to change my reservation literally hours before. Last minute travel changes with flight, accommodation, etc can be hectic but Israel helped make this part easy for me. Overall, great experience and will definitely be staying here again!

Had a wonderful stay! Everything went smoothly and the space was beautiful. Would definitely recommend!