House vacation 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.

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.

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

Keith was so super sweet! Always texted back if I had a question. He was welcoming since our first contact. The house was amazing. It felt like home and we treated like home. Definitely will be back again. Absolutely stunning!!

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

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

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.

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!

Comfortable property on the water, with new deck. Great views. Maria is very responsive. Would stay here again.

Above & beyond! The home was in a great spot with an excellent price. Tim was extremely accommodating with our requests and communication was perfect. The refrigerator was stocked with eggs and butter. The cupboards were stocked with staples and all the supplies we needed - toilet soap, shampoo, Kleenex, paper towels, bath towels, snacks, granola bars, etc. We would highly recommend this Airbnb to anyone and would use again. Thank you!

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!

I have stayed at dozens of Airbnb’s and this is in my top 3! The home is perfectly appointed, super clean, well stocked, cozy, and beautifully decorated! The master bathroom is magazine worthy. Jeff was very easy to communicate with and let us check in early. My family plans to make it an annual trip.

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!!

Danielle’s place was the perfect spot for a short getaway. While it’s on the smaller side, it was comfortable and worked out great for two people and our two dogs. We didn’t spend a ton of time indoors, but we loved relaxing by the outdoor fireplace in the evenings, such a nice touch! It’s about a 20-minute drive to downtown Annapolis, offering the best of both worlds: close to the city, but a peaceful escape from the hustle and bustle.

We had the best time at this Airbnb. I booked this house MONTHS ahead of my sister's bachelorette, and the host was very responsive to all of my messages from the very beginning. I did ask for an early check-in (whatever that may have been) and they allowed us to check in a full four hours early, for a small fee. The house is on a quiet street in a nice neighborhood, which was perfect for our lowkey weekend. We did drive into downtown Annapolis for a boat day, brunch, and shopping, all which was very easy to do. The house itself is beautiful and clean. There was plenty of space for our entire party (8 girls) and tons of extra towels for everyone. The kitchen was nicely stocked with every cooking tool we needed, including ice and water bottles in the fridge. They even provided the firewood for the amazing backyard, which for some reason I thought we'd have to find for ourselves. All this to say, book this spot, and pack light, you won't regret it!

This house was in a beautiful location. Everything was clean and comfortable, thoroughly enjoyed our stay. You cannot beat the views from the main level. Katie was communicative and we were even able to get an early check in!

Tara and Theresa were great! The place was just what was needed in every way! The host always made sure that the house was up to our needs and anything was immediately addressed. A top tier host without a doubt! Don't hesitate to book :)

The perfect mom and teen boy getaway! The house is on the water with gorgeous sunsets and super clean! My boys attempted fishing daily even without any luck. Altho we didn't kayak because of the choppy water, its great location (there's a ladder at the private pier or a public launch a few yards away) We cooked and ate in a few nights and also enjoyed a local spot on the water (The Narrows). The neighborhood was quiet, relaxing and peaceful. We enjoyed a visit to the Chesapeake Environmental center (abt a 12 min drive) which was a hidden treasure. The Chesapeake Outdoors (recommended by our host Jeremiah) was a great find for bait and info from the locals. Morning coffee on the patio and evening sunsets on the pier were some of my favorites, along with the spacious open floor plan (yet privacy with bedrooms). Jeremiah was super responsive and kind! We'll be back to kayak, fish more, enjoy the hot tub coming soon, the serenity and gorgeous sunsets! (maybe we'll even bring dad -LOL)

Cannot put into words how wonderful our time was at Away at the Bay! Just left my soon-to-be SILs bachelorette trip and the entire weekend was nothing short of incredible. Thank you so much to Ryan and Eric for creating such a wonderful experience in a place that truly feels like home but BETTER! Memories we will cherish forever.

Great spot! The beautiful home looks just like the photos. My family had a great, relaxing weekend!!

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.