Waterfront vacation rentals in Annapolis

It was an extremely lovely apartment overlooking the beautiful Chester River! The apt was spotless, warm, inviting & had lots of amenities. Walter was beyond helpful: he rescued me when my rental car broke down out of town on the highway in the rain. You can’t ask for more than that!! Thank you for a wonderful stay!!

Perfect locarion for walking to everything in Annapolis! The space is small but comfortable and in a very cool historic neighborhood. Host was very communicative. Would definitely stay here again next time I'm in the area.

WOW! My family and I cannot say enough great things about Jeanne's Airbnb already planning our next trip! First off the property is an oasis in itself with a massive deck overlooking the inlets of Chesapeake Bay we woke up every morning to a beautiful blue heron eating breakfast right on the dock, having access to kayaks to explore the waterways was a huge bonus too, not to mention the gazebo with a fire pit we enjoyed roasting marshmallows and talking about the days adventures as a family. The inside of the Airbnb is extremely well thought out with every amenitie that anyone could ever ask for, from a well stocked and equiped kitchen, to the king size master bed with luxurious soft linenes, to the heated fan that greets you after a perfect water pressure shower. Seriously, this place is perfect a hidden gem for sure with easy access to so many wonderful Maryland attractions. Can't say enough great things about this experience and Airbnb can't wait to return!

I can't say enough good things about this property and Dana. The apartment was pristine and adorably decorated with coastal decor. The bedding was beautiful and comfortable. The property itself is just stunning and beautiful, and Dana was incredibly responsive. She provided coffee, bottled water and local treats as well. Chef's kiss. I only wish we could have stayed longer! I hope we have a reason to come back in the future.

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

We had a wonderful stay at Brenda’s place! The pool is amazing and the whole outdoor area is great. With the grill, chairs and tables, outdoor fire (two of them!) we had such a great weekend escape. Very quiet area, we didn’t see the hosts the whole time which made it feel private. They were so responsive and helpful all weekend. Wonderful stay and we will definitely be back!

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.

Michaels place was amazing enjoy every minute of it wish I could had stayed longer but I know for a fact when I come back I will be staying here.

I would definitely come back here. If you want to unwind, decompress, or just slow-living for a couple of days, you won’t find a better place. The sounds of small waves all day and the birds chirping in the morning were almost as good as the break-taking ocean view. Better than advertised. I could sit in the cabana and read all day.

We loved our stay! This is probably my favorite AirBnB that I’ve ever stayed in! The house is absolutely gorgeous - so historic with a lot of charming and antique touches. Beautiful chef’s kitchen with all the equipment you could need! The bedrooms and bathrooms were more than enough space for our family vacation. We loved having two sitting rooms to spread out, and mostly hung out in the open concept kitchen-living space. Very walkable to downtown, we never ended up needing to drive or uber during our whole long weekend (but bring comfortable shoes because it’s hilly). Nearby garage for parking is $25/night, but there is 2-hr parking on the street along the house where you can load and unload your car.

I stayed at this Airbnb over the past weekend and had such a wonderful time! The house was clean, welcoming, and had everything we needed to feel right at home. My favorite part was definitely the dock and the little beach area behind the house. I spent hours lounging on the beach chairs, soaking up the sun, and listening to the waves — so relaxing. It was a bit early in the season to really go crabbing, but I had a blast learning how to set the traps. We even caught one little crab and let him go — a fun little adventure! The house manual and guides were super helpful, with clear instructions that made everything easy to figure out. Overall, it was a peaceful, fun, and memorable stay. I’d absolutely come back again. Highly recommend!

The house was a perfect for our stay to attend our daughter’s wedding. It was peaceful and quiet but still close to the venue and amenities. The open living, dining, and kitchen area made it easy to host the bride’s six friends for a wedding morning get together. It was lovely to sit on the dock and enjoy the water in the evening. Leandros was responsive to emails and he provided everything that you could possibly need while there. Thank you!

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.

We had the best time enjoying Jody and Gail's beautiful home! The views were incredible, it was so peaceful, and the house had every amenity we could have wanted. A highlight was kayaking and swimming in the cove right to the side of the home. We cant wait to come back!

The location was unbeatable. sipping tea by the water in the morning and watching kayakers and boats sail by, the peaceful sound of the waves and view made every moment magical. The home was spotless, beautifully decorated, and well stocked. Our host was responsive and kind. Whether you are looking for romantic getaway, family vacation or place to unplug and recharge, this waterfront home is perfection.

Natalie’s place was just like the pictures. Everything was clean and well stocked for our stay of 6 adults. The sunsets were beautiful from the dock and the kayaks were a definite bonus! We enjoyed time outside on the dock, deck, and in the hot tub! The beds were very comfortable and our stay was great!

My family of 4 had a great stay at Ricky's place. The location couldn't be beat for going to the National Aquarium and Oriole Park. The place was really comfortable and clean. The steep stairs we read about in other reviews were not a problem for us.

All I can say is AMAZING! The view’s looking over the water, the building was like a 5 star hotel, concierge etc…. This is a perfect spot to relax and take a breather ❤️❤️❤️❤️❤️

We stayed at Gerald's wonderful Airbnb for our daughter's surgery at JH Hospital and it was perfect in every way. It is one of THE best Airbnb's we've stayed in, and we've stayed in many all over the world. His place is clean, stylish yet comfortable (including the mattresses), and well stocked, with lots of appreciated amenities. As a host, Gerald is very helpful, communicative, accomodating, and friendly. It is clear he values and prioritizes his guests' comfort and experience. It is conveniently located - walking distance to everything the Inner Harbor offers, Camden Yards, and much more. We definitely plan on returning to Gerald's place (under better circumstances)!

Great host, great location. Walkable to great restaurants as right over the bridge from Main Street Annapolis. The pool is literally right in front of the apartment overlooking the water and the boats going by. The place is not huge but location, location, location.

My family & I booked for three nights. Thought it was a beautiful and private little area, and just a couple steps away from the beach and a pool. Very quiet and away from noise which was a plus. The house itself was lovely and mostly clean. There were board games available and my kids had a fun time playing with them. We enjoyed barbecuing using the grill provided on the balcony which was nice as well. A plenty of towels and anything you need in the kitchen! Other than a full trash bag left over in the kitchen, finding some clothing items from other guests (I’m assuming) in drawers, and the keurig having what looked like mold inside. Pretty small things when looking at the big picture though. Will most likely come again & we enjoyed our stay!

Sean’s unit is an amazing option for those who love a great place to relax with an amazing view. Sean is a great host and very communicative.

Wonderful location in the heart of Georgetown. The place lacked a living room but this was very clear in the description of the place so all good! Walk out and enjoy Georgetown and DC!

What a perfect weekend get away. The place was perfect. Extremely comfortable beds, lots of pillows and two deck areas outside. We cooked outside 2 nights - and loved seeing the bay from the deck. We used the nearby tennis and basketball courts, and spent the days visiting wineries and neighboring towns, and driving through the countryside. Groceries and restaurants require some planning and some driving. Loved our stay!