House holiday rentals in Annapolis

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.

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!

Beautiful house! Clean, well maintained, and exactly as described. The host was easy to communicate with and very responsive throughout our stay. The space felt comfortable and welcoming, and everything we needed was thoughtfully provided. We had a great experience and would definitely love to come back!

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 home was spotlessly clean and looks just like the photos. The beds were comfortable and there was plenty of room and seating for watching movies. The showers and bathrooms were great, and it was nice to be able to do laundry. We used the pool towels provided. The kitchen was stocked with basic items - there is a keurig coffee pot only and they provide pods which was nice. A few things we didn’t realize: the driveway is very steep and we scraped our van trying to go down the first time - you need to go in at a certain angle. The noise alarms are very sensitive and it went off when we were watching a family movie, and we had to answer a text from Tanya. This was honestly a bit annoying. We enjoyed the pool and hot tub! When the jets were turned on, the hot tub become filled with much foam from all the chlorine so we didn’t turn the jets on anymore. We hiked from the house into the state park and did a 5 mile loop, which was very convenient.

Daniel’s Home was beautiful and he made this special event for me and my family able to celebrate my sons 26th Heavenly Birthday a success We were very comfortable and it really felt like home the pool was very clean and the Home was very spacious and squeaky clean I would love to Book Daniel again He was a very nice and friendly Host that responded to any questions we had he made communication easy me and my family really enjoyed our self and yes he’s reasonable and you definitely get what you paid for and more Thank you again Daniel

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

My family and I had a great time staying at Jennifer's! it was a great home for a mixed generation vacation. We loved the open concept main floor, it made it easy to all spend time together. We will definitely consider her place again when we visit Annapolis!

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.

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 had a great stay here - it was super clean and had lots of charm! I loved the extra goodies around the house in case we forgot anything. Matt was great and we'd definitely stay here again in a heartbeat if needed!

We were in town for night. Place was super clean and convenient. Walkable to restaurants but may want to opt for the car. Super convenient if you are attending a football game. Exactly as advertised and what we needed. Hosts were super responsive.

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.

The house was perfect for us. We were retiring from the Navy and did our ceremony at the Naval Academy. We had guests stay at the Westin which was immediately across the roundabout. This made the home a very convenient 2 minute walk from where our guests were staying. The backyard is wonderful and worked perfectly for our get together with friends after the ceremony. Our kids had an entire finished basement to themselves to play with their friends. It really could not have worked out better for us. The house was perfectly clean and smelled wonderful with great furnishings throughout. You can tell Laura makes a lot of intentional choices to make guests feel right at home.

Our family had a great stay! The amount of space worked well for us and we enjoyed coming back to the house in the evenings to relax after being out and about in town all day. The location can’t be beat, being centrally located and walkable to everything. Jared was very flexible and accommodating regarding a check-in request, making our trip much smoother! I would absolutely recommend his place in the Annapolis Historic District!

Can’t say enough about the location! Perfect walking distance to everything and the pier. We will definitely return!

Excellent hostess, responsive and helpful.

I was having some contractor work done at my own home and I was having trouble focusing in my office, so I sought an escape on AirBnB. I spotted Tammys property, she was accommodating, let me check in right away, the home was fantastic. The best part was the very large, securely fenced backyard, which my dog adored. Thank you for a wonderful stay, I will return.

Wonderful host, great communication , very accommodating was able to check in early , had everything needed plus extras , water , snacks , milk, juice ect… my guests and I where very pleased, great backyard. Patio table and grill was a nice touch .. can’t wait to stay again and use the fire pit. 5 stars !!!

I recently had the pleasure of staying at Caitlin's Airbnb in Annapolis, Maryland, and it was an experience to remember. From the moment I arrived, Caitlin's warm hospitality was evident. She went above and beyond to ensure that I felt welcomed and comfortable, making the entire stay feel like a home away from home. Her responsiveness was outstanding—any questions I had were promptly answered, and she was always available to provide helpful recommendations about the local area. This level of attentiveness truly set the experience apart. The property itself was charming, clean, and thoughtfully arranged, adding to the enjoyable memories I made during my stay. Whether it was relaxing in the cozy living area or exploring the beautiful surroundings, every moment was delightful. Caitlin’s dedication to her guests’ comfort and satisfaction made my visit exceptional, and I would wholeheartedly recommend her Airbnb to anyone looking to create wonderful memories in Annapolis.

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.

Our ideal Airbnb includes comfortable beds, peaceful surroundings, fresh and clean linens, a well-equipped kitchen, and we found all of these in this property! The view from the master bedroom is one we will miss waking up to each morning. Great to be able to walk to the small, private beach, as well. Hope to return!

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.