Holiday rentals with outdoor seating in Shady Side

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!

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.

Laurie’s place was just liked it is described. It’s located in a beautiful area and walkable to all the attractions in Annapolis Maryland. I would recommend it and I would stay there again if ever back in Annapolis! Thanks for wonderful stay!

Scott and Melinda's place was perfect for a peaceful getaway for our family of 5. The water was so nice to wake up to and fall asleep hearing the water move by! The thought of all the basic needs and had everything easily accessible from fresh eggs from their chickens, a great variety of coffee pods and creamer, and all the other small needs that come up while staying in an airbnb. This was great since it is off the beaten path. If you are looking for some peaceful family time or a secluded retreat with friends, this is a perfect place!

The place was wonderful. It was wonderful timely responsive My Children enjoyed themselves. My wife didn’t complain and she loves to complain so she didn’t have one complaint which made everything absolutely perfect and I would definitely book there again in the next time I visit Maryland. It was wonderful experience.

Fabulous house in a terrific location. The house was very clean and Rick was a great host.

Nicole was a great host. Her place was nice — uncluttered, kitchen had everything you need, it was nice sitting on the sofa and looking out at the water. The beds we very comfortable.

only stayed for one night but i was very comfortable. the toiletries and snacks were an appreciated added bonus.

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 home was wonderful and quaint. The bed was comfortable, the kitchen and living area were perfect, and my stay was enjoyable. I'll stay again when I visit the Annapolis/DC area in the future! Thank you Lynn!

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!

Love this clean calm space-the balcony was wonderful. Mark was super responsive, checked in on us and we had everything we needed-especially in the kitchen. Great location for walking to restaurants and stores. Will definitely stay again!

We absolutely loved our stay in this beautiful condo. Pristinely clean and spacious with everything we needed to be comfortable. We loved the modern decor and appreciated the extra thoughtful amenities. A wonderful place to return to after a long day of walking in DC. We would definitely stay here again and would highly recommend it to others.

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!

We had a peaceful stay. It was quiet, clean and all house instructions were detailed and easy to follow. Communication was good and efficient! So much nicer than any local hotel 😊

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!