Waterfront holiday 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!

This was unanimously our family's favorite AirBnB! Dana and Mike are the dream hosts! Our accommodations prior to our scheduled arrival were cancelled last minute and they immediately jumped in to help. They were extremely considerate of our privacy whilst being right next door but also quick to respond when we reached out to them. We could not of asked for a better mini-vacay in the middle of our travels. The beautiful surroundings, welcoming accommodations and hosts, attention to detail throughout amenities and decor, and impeccable cleanliness were top-notch. We really enjoyed the heated pool too. The kitchen and grill were easy to navigate and stocked with all essential items needed to prepare meals. The Monocle Meat Company and Lovepoint Deli & Wine are great local shopping options. If cooking is not in your plans, Avanti has amazing pizza. Thank you Dana and Mike for going above and beyond to make us feel at home! Heron Roost is now our must stay place when visiting MD.

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

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

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.

Our Airbnb stay was absolutely fantastic! My family and I really loved all the amenities. The waterfront view was stunning, and we had a great time grilling and just hanging out together with friends and family. It was truly a memorable experience! I would definitely recommend this Airbnb for a family getaway and to have a peaceful time enjoying the water and the beach. I definitely will come back again!

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 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!

Adam’s place was exactly what we needed for our wedding at Chesapeake Bay Beach Club, so spacious and within a 7 min drive of the venue! He was also very helpful and flexible about our check-in and check out needs! Fantastic stay, would absolutely return!

Our stay here was great. Clean space with awesome views. The sleeping situation was funky but perfect for our friend's wedding weekend. We hope to come back!

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!

We had a wonderful time during our visit. The peaceful environment on the water was just what our group needed. Thank you!

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!

I was impressed by how clean and uncluttered Ricky’s place was. It was definitely a benefit that parking was included, though it was a little awkward loading and unloading and getting to and from the parking garage. Garage was a block away and secure with lots of cars nicer than mine haha.

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!