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!

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 house was perfect for our stay in MD. Our family of six was very comfortable here and our kids loved the pool and spa. The house is clean, cute and very cozy. Tanya was very quick to respond and great to work with!

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

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

We had an amazing stay at Cathleen’s home in Edgewater, Maryland! Cathleen was the single most attentive and thoughtful host we've ever had on Airbnb. The home was beautiful and had everything we needed for a comfortable stay. The kitchen was fully stocked with all the essentials, making it easy to prepare meals. There were plenty of extra towels, and we loved the added bonus of having Hulu and Netflix preloaded on the TVs. Everything was perfect, and we can't recommend this place enough. Five stars all the way!

Very quiet location but not far from amenities. The home had an attention to detail that not all air bnbs do (for example enough towel hooks for everyone staying!) as well as basic cooking amenities

Gwen’s peaceful waterfront retreat was truly just that—peaceful and relaxing! From the moment we arrived, we felt welcomed and at home. Gwen was a gracious and responsive host, making sure everything was perfect for our stay. The property was filled with thoughtful touches and amenities that made our visit incredibly comfortable: a charming gazebo dining area, outdoor kitchen, a coffee bar, fresh flowers (such a lovely touch!), and more. The beds and bedding were comfortable, ensuring a great night’s sleep. The neighborhood is beautiful and quiet, with access to a private beach area that made the whole experience feel extra special. The highlight of our stay was undoubtedly the incredible dock experience—sitting right on the water, surrounded by nature, with comfortable chairs perfectly placed to enjoy morning coffee, afternoon sun, or stunning sunsets. Highly recommend for anyone looking to unwind in a serene waterfront setting!

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!

We booked Laura’s property 2 years in advance for Commissioning Week. Throughout the 2 years she answered our questions quickly and effectively. The house had room for 2 parents, 2 grandparents, and 1 sibling. Basement area is nice and private. The house looked just like the pictures. The driveway is hard to get out of during busy times, as it is on a roundabout. However, it was easily walkable to the stadium in less than 13 mins (perfect for graduation/commissioning week, as you have to pay for parking if you want to take the shuttle from the stadium to the yard). It is also walkable along West St, where all the shops and restaurants are. The furthest restaurant is 1 mile away, but there are many spots that are closer. It’s about 1.2 miles from Gate 1. You can take the free downtown shuttle that goes along West St if you don’t want to walk all the way. Overall a great place to stay when visiting a Midshipman or celebrating graduation!

This home is right in downtown Annapolis. You can walk to many historic sites, restaurants, and bars. There is no parking, so you must park in one of the garages and walk to the house - but it isn't far. Street parking is limited to 2 hours for non-permit holders. This was one of my favorite airbnbs in Annapolis (and I've stayed in many). It was exactly as pictured/described. It was bigger than expected with lots of space for a larger group. The living room was nice with lots of seating and a large tv. We used the pullout sofa in the second living area and it was super comfortable. The bedrooms and bathrooms were very nice - great showers and deep soaker tub in the en suite. I slept in the king bed in the back bedroom and it was wonderful. The kitchen and dining area were very nice and we gathered there much of the time. We enjoyed the front porch for morning coffee and evening drinks. The back patio was also another nice space to sit and relax.

Very peaceful surroundings, you are out on a point overlooking the bay, with lots of outside space to relax in the mornings to enjoy your morning tea/coffee. I loved having the real fireplace and enjoyed an evening fire on the more chillier evenings. Felt at home and comfy.

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.

We had a fantastic experience. The home is full of charm and character. It was spotless upon arrival and had everything we needed for a relaxing stay. The location is unbeatable — just a short walk to the waterfront, and plenty of great restaurants and shops. We especially loved how quiet the neighborhood felt despite being so close to downtown. Communication with the host was seamless, check-in was easy, and every detail felt well thought-out. We would absolutely stay here again and highly recommend it to anyone visiting Annapolis.

Lovely place to stay , very close to downtown Annapolis! Beautiful home, super clean , well stocked kitchen to cook, have dinner , or just relax ! Extremely comfortable bedrooms with 3 king size beds ! Bathrooms lovely well stocked with comfortable towels ! Would and will easily stay here again when we visit Annapolis as my daughter and family live there ! Thank you Jenn

Sarah was a fantastic host and the home was perfect for us. Very convenient location, clean and with a number of unexpected conveniences that really made it feel like home. The little things really added up here (the decks of cards my family played games with, the expansive coffee setup, the extra super soft pillows on each bed). Thank you for the stay, Sarah!

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.

Matt’s place was excellent.He had anything under the sun you would need to stay there. The place was perfect for four people. Very clean and comfortable.

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!

Wow, what a place!!!!! Everyone could be so lucky to not only stay here but have such a wonderful host as Beth was for us! The home is a little slice of paradise for anyone wanting to just decompress, relax and also enjoy the water and abundance of nature surrounding this home. From the inside being spotless, comfy to the amazing yard and views, this property is better in person in every way. Thank you for hosting us Beth, we loved it!!!

Jessica was so sweet and thoughtful. She provided muffins from her favorite bakery in town and stocked the fridge with drinks my family could enjoy. She was so accommodating and flexible to our travel plans as well! Our family had a blast playing Clue and watching movies at night. Our mornings and afternoons were spent on the porch in rocking chairs or on the back patio enjoying the quiet. We loved it so much and we will definitely be back!

Cannot recommend Tamara’s home enough. It is in a perfect location close to downtown Annapolis but in a quiet neighborhood. We especially loved the outdoor space. Her home is spacious and comfortable with no detail missed. The coolers and towels came in handy for our electric boat rental. Next time we will have to try the kayaks! We were in the area to visit our daughter and celebrate my husband’s 60th birthday with the family. We walked everywhere with so many wonderful restaurants only a short walk away. Thank you for an amazing stay!