Waterfront holiday rentals in Deale

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!!

Amy and her place were lovely for our family of 4. With two littles it worked very well and Amy even had toys for us- we also used her provided pack n play and some baby essentials. King Bed was extremely comfy, moderately firm. Shower was very nice. Cozy, comfy, had everything we needed. Amy was very responsive and helpful. We would gladly come back! Thanks Amy!!

Lisa’s place was amazing! My daughter and I had a great visit. The location is perfect for going into Annapolis. We will definitely be back. Thank you for a great few days!

What a calm and peaceful private retreat! My fiancée and I spent a couple of days enjoying the brisk bay breezes and beautiful sunsets at Vickie’s. Everything was exactly as advertised and Vickie (and Scott) are true treasures—extremely responsive and thoughtful hosts who want you to have everything you need. Plus, their knowledge of the area gave us a great introduction to Leonardtown. So much more to the area than we thought! Whether birdwatching from “the best view on the block” or reflecting on the glider by the bay, we loved every moment of quiet and can’t wait to visit again. Thank you!

Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.

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.

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.

My mom, sisters, friends and I enjoyed a relaxing fun filled time at the Coastal Oasis at the Chesapeake for our Mother's Day Retreat. The view is amazing and truly can be seen from every room in the house! Being able to see the beauty and calmness of the water helped each of us kick back and let the stress melt away. The big dinning room table allowed all of us all to enjoy breakfasts, dinners and touching conversations together. My guests loved the décor and raved about every detail. The beds and furniture were comfortable and house clean. I would definitely come back!

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!

A wonderful stay at Stephen's place for our son's USNA commissioning. Although he lives in the 2nd floor, he was very respectful of our space - we hardly knew that he was there. He was very responsive when you needed him and helped us to host a gathering of friends and family to celebrate at his beautiful home on the water. Highly recommend.

We truly enjoyed our stay at the Colonial Beach Airbnb. The house is very cozy, well stocked, clean, updated and Carmen is a thoughtful host. The deck is a great area to relax overlooking the water and a few tried their luck fishing off the dock. Very nice!

We had a truly wonderful stay at this beautiful home! The place was spotless and very well maintained, and we felt comfortable from the moment we arrived. There were plenty of activities to enjoy as a family, and we created some unforgettable memories here. The host was incredibly friendly and responded quickly to any questions we had, which made everything even more enjoyable. The surroundings are absolutely stunning, and the sunset views were nothing short of magical. We would love to come back again!

this is a really beautiful place to stay at, thank you 🙏

This house was perfect for our large family. It had everything we needed and was very comfortable. The place was very clean and nicely decorated. The kitchen is well stocked with plenty of dishes and cookware for a large group.

I recently hosted my wedding at Rousby Hall, and it was truly the most unforgettable experience. The grounds are absolutely stunning — from the waterfront views to the beautifully maintained gardens, every corner felt like a dream. The historic home itself is full of charm and elegance, offering the perfect backdrop for both our ceremony and celebration. Polly, the host, went above and beyond throughout the entire process. She was incredibly helpful, kind, and responsive, which made planning feel effortless. Her knowledge of the property and attention to detail ensured everything went smoothly. I can’t imagine a more perfect venue or a better person to work with. Rousby Hall gave us memories that will last a lifetime, and we’re already talking about returning for future celebrations. If you’re considering this venue — do it! You will not regret it.

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.

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.

Nadia was fantastic to work with as we were dealing with a stressful situation that required a quick exit from our home. She made every effort to get us in early even with a same-day guest departure. The apartment is absolutely perfectly stocked! So many thoughtful items made our stay very comfortable and easy. I wish we’re could have stayed longer to enjoy it all! The pond and geese/ducks outside the master bedroom were lovely (and made good sleeping white noise). Highly recommend if you’re in need of a convenient place in the area!

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!