House holiday rentals in Shady Side

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

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 were very relaxed at our stay. It was quiet and the ocean was just down the street. We would go and sit on the bench and just listen to the waves.

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!

This place is fantastic for a stay. Daniel is super communicative and quick to respond. Plus, the pool is impeccably clean.

This place is an absolute gem. We’ve stayed in everything from sleek modern homes to charming older properties, and this one truly stands out. Although built in the early ’90s, it has a unique colonial charm that feels timeless. The bedrooms and bathrooms were spotless and comfortable, with plenty of drawer and closet space for everyone. While it’s listed as a four-bedroom, there’s an additional upstairs room perfect for an air mattress, making it easy to accommodate up to 10 guests. What really drew us here was the peaceful setting—and it didn’t disappoint. The pool sits in front of the house, while the back opens to serene water views. Both areas offer spacious, covered and open seating to relax, rain or shine. In fact, we spent our first rainy evening on the covered back porch, just soaking in the view. We also brought our dogs, who absolutely loved having so much room to explore. The fully fenced yard gave us peace of mind, which made the stay even more relaxing. The hosts were

We had a wonderful stay! Virginia was incredibly responsive and made the entire process smooth from start to finish. The house itself was great—clean, comfortable, and well-equipped—but the real standout was the amazing view and the outdoor space. Our family especially loved spending time outside; it quickly became a favorite hangout spot. This home was absolutely perfect for hosting my son's graduation celebration, and it helped make the occasion even more special. Highly recommend!

A great place to enjoy a long weekend at the Eastern shore in Maryland.

The house is easy to find and has a great outdoor seating area. The house and linens were very clean and Sekai even provided fresh fruit upon arrival! The stocked Kurig pods were very handy and appreciated in the morning as well. From this location you have easy access to downtown Annapolis and all of its history. If you go the other way out of the neighborhood, you can browse the mall and TownCentre for all your other shopping needs. This is a pet friendly house that you would not know there had ever been a dog in there. Fortunately, ours was well behaved so you still won't know a pet was ever there! He enjoyed walking the large private yard.

Heather’s directions were clear, and checking in was seamless. The place had everything we needed for our overnight stay while in town for a wedding. Thank you!

It was a great stay and a perfect location for our quick family back east. It was very comfortable, clean and a the right size for our family of 4. It was nice to have our own place to stay and not to far from our family. We didn’t spend much time in the town but it looked cute with shops, cafes and restaurants. We had great communication with Maria, she was very quick to respond. Thanks for a great and comfortable stay!!

My husband and I stayed here for a month while we had work done on our boat at a local marina. The location is perfect for access to the local marina as well as all the restaurants in Deale. Yen was super responsive as was John. They responded to all our questions in a timely manner, and were always very kind. The home is well laid out, and worked perfectly to use as a homebase. Good wifi, comfy couch, comfy bed with good pillows. The master suite is gorgeous and well lit. Kitchen is well appointed and had all the appliances/utensils we needed. Had several work spaces that were great for zoom calls and other "office" type work. The tap water didn't have any odors. Enjoyed having coffee on the front porch with a lovely view of the Chesapeake and the screened in porch in the back was great as the evening bugs came out. Highly recommend this home!

Andrew is a great host. We really enjoyed our stay! The property was very clean and felt like home. We enjoyed our walks to the water with our dog. I enjoyed the sunroom for reading. Neighbors were also extremely friendly(offered us bbq often)! Great place to stay overall!

We had a very enjoyable stay at this perfect River House. The place was warm and comforting, with some of the most amazing views you can find. We arrived shortly after check in time, and easily let ourselves in with the lock box code & key. Everything inside looked just like the pictures, and we weren't disappointed! If you're looking for some beautiful river views, right on the water, with your own private water access and dock, this is the place for you. We were in town for a wedding a few houses down, and this place couldn't have been any better for us. We were able to walk to & from, which was a huge bonus for after the reception...Cheers :) We enjoyed eating out a couple times in town, and really liked Brick Wood Fired Bistro & Traders Seafood Steak & Ale. We would highly recommend this property for anyone looking for a peaceful river stay, and will surely return someday in the future! Thanks for your hospitality!

We stayed in this house for our son's Naval Academy graduation/commissioning. It was absolutely perfect for our group. The drive across the bay bridge took anywhere from 35-45 minutes depending on the traffic. At no time was the traffic as bad as we've experienced it on the DC side of Annapolis. We crossed the bridge 1-2 times a day during our 7 day stay. As soon as you get to the island and head south there is no traffic and it's a beautiful, peaceful drive. The house is perfect for entertaining with two large rooms inside on the main floor. There is a large island in the kitchen room which makes for a great serving area. It rained during about half of our visit so we made good use of the space indoors. Our children used the fishing poles, kayak, soccer nets, ping pong and fooseball table. Negin was very responsive in answering our questions and even worked it out so we could check in early. We would definitely stay there again if we had the chance.

This was a fantastic house for our family vacation. It has beautiful views of the bay, a large backyard, plenty of room in the house, and is clean and well maintained. The house is also a short walk from beaches and a nature preserve with excellent hiking trails. The home is a short drive to D.C., state parks, Watkins Regional Park, and Mount Vernon. Teresa is a fantastic host that goes the extra mile. She allowed me to borrow a computer keyboard as I forgot mine at home. Teresa also contacted me to ensure we had everything for a great stay. We will definitely stay here again the next time we visit the area.

The place was everything I wanted for my vacation. I will come back for another relaxing weekend. Many thanks to the kind and helpful hosts.

Gwen’s peaceful waterfront retreat was truly just that—peaceful and relaxing! From the moment we arrived, we felt welcomed and at home. Gwen was a gracious and responsive host, making sure everything was perfect for our stay. The property was filled with thoughtful touches and amenities that made our visit incredibly comfortable: a charming gazebo dining area, outdoor kitchen, a coffee bar, fresh flowers (such a lovely touch!), and more. The beds and bedding were comfortable, ensuring a great night’s sleep. The neighborhood is beautiful and quiet, with access to a private beach area that made the whole experience feel extra special. The highlight of our stay was undoubtedly the incredible dock experience—sitting right on the water, surrounded by nature, with comfortable chairs perfectly placed to enjoy morning coffee, afternoon sun, or stunning sunsets. Highly recommend for anyone looking to unwind in a serene waterfront setting!

I stayed here the week of my wedding and it was absolutely perfect! From waking up each morning to have coffee on the dock with my pups and husband, to the beautiful views from each room in the house, we truly had a lovely time and chose the right Airbnb for such a special week in our lives.

The place was wonderful. The house was clean. The beds were comfortable. The kitchen was more than well equipped. The setting was beautiful. The outdoors was perfect. Great outdoor furniture. The Bayview was unbelievable. The house in relationship to recreation is spot on. I can’t say enough great things about the place. I will definitely be booking again and again.

The place was spotless and had all the amenities we needed for a 4 day stay. We enjoyed the water view and had a crab feast on the deck overlooking the water. It was a perfect Memorial Day weekend.

The description of Joel's Annapolis home is an accurate description of his wonderful home. The most outstanding features of this property are: the waterfront location --> unobstructed panoramic views; serene setting on a quiet street and there are lots of other pluses. The house was super comfortable. Everything was in working order. I appreciated the workout equipment --> not lots of stuff but enough to get some indoor exercise that I like to do each day. Walking up and down the street --> neighbors were all very friendly. The kitchen is fabulous. It only took about 15 to 20 minutes to get to the center of things to do and see in Annapolis. While we did not use much of the outside furniture, the outside furniture is plentiful and looks comfortable. A big thing for us is cleanliness --> the house is immaculate. We will probably make a return trip in the future and would appreciate the opportunity to stay here again.

Jon is a fastidious and generous host. Unlike many Airbnbs, this is the home that Jon lives in, and he's clearly someone with tremendous pride and joy. Every detail from the landscaping to the furnishings to the little details of making our stay feel cozy were perfect. As other reviewers have noted, the location is fantastically convenient. We also brought our binoculars, which came in handy for the variety of birds attracted to the old, large backyard trees. If you are into birding, only 7 minutes away is the amazing Smithsonian Environmental Center, which has great walking trails through the woods and some pretty spectacular waterfront views! We would most definitely stay here again!!

Staying at Alena’s place in Annapolis was truly a wonderful experience. From the moment I arrived, Alena’s warmth and friendliness made me feel completely at home. She’s an incredibly gracious host who goes above and beyond to make sure her guests are comfortable. The home itself was immaculate. I especially appreciated that it was an organically cleaned home. Rare find. Knowing that non-toxic products were used and that the environment was being considered added such peace of mind during my stay. The overall feel of the home was incredibly cozy and inviting. Every space felt thoughtfully curated to promote comfort and relaxation. It truly felt like a home away from home. Alena’s care for her guests and the environment shines through in every aspect of the stay. I would absolutely stay here again without hesitation. Highly recommend!