Holiday rentals with a fire pit in Annapolis

Perfect find - beautiful apartment, exceptionally quiet considering it is on the lower level, awesome view from the patio, all amenities that one could need - in addition, Michelle is awfully considerate and easy to communicate with. Looking forward to my next stay.

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!

This air b&b is in a beautiful setting with plenty to do (kayaking, hot tub, fire pits, bird watching, etc). It's also very centrally located so we could easily get to more populated areas in no time. The most stunning part of the house is the master suite in my opinion which is on the upper level (the upper level is shared with another apartment, but you don't really hear the air b&b tenants of this suite and it's completely separate with a separate entrance). Stunning views from both the master bedroom and the bath tub in the master suite! The downstairs is also quite lovely with two regular bedrooms, one small bedroom, and a sun room that has a pull out couch (we didn't use it). It's a lovely house to entertain in. It has personal photographs to the owner downstairs that speak to the family's history. The owner is communicative. The overall experience was quite lovely. We'd be happy to return.

Catherine’s house was perfect for our attendance of my nephew’s Naval Academy graduation. The house was stocked with everything you needed and then some. Catherine made a special point to get mosquito spray, candles, etc. but we were so busy and didn’t have an opportunity to relax outside. As mentioned by others - parking is the main downfall. If you don’t have an issue walking, the parking garage wasn’t far away. It was much faster to walk to/from downtown with all the traffic so we left the car parked most of our trip. Catherine was fabulous to work with and I would definitely book this house again should I need to return to Annapolis.

Jared was timely with every response and very accommodating!

We had a great stay! The yard was perfect for our dog and playing with our grandson. There was plenty of water and the house met all our needs. The neighborhood was fantastic and we loved taking walks and seeing everyone else out walking their kids and dogs! Definitely will come back!!

We had a great weekend at this cottage. Comfortable layout, great dock, and a beautiful view. We hope to return.

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.

Absolutely wonderful accommodations in an amazing location . Marshall and Eva were so friendly and helpful. Cozy, clean, perfect !! Thank you so much !

This is a great place to stay and tour the DC Metro area - provided you have a car. Most days it would take us 30 minutes to get to and from DC though if we hit rush-hour, it was as long as an hour. The space is tidy and great. My kids love the pool, though it was a little cold for me-they swam there every night. Jennifer is great to communicate if you have any needs she gets stuff done right away. Note that there is only one bathroom, which can be a pain if you have a full house of six people. The washer and dryer are small so it will take you longer if you’re used to a full size. She had all the cooking methods and appliances available. The theater room has Netflix and Amazon prime ready for you to watch a show. There is even a popcorn maker. We did not use the gym, but it was nice - comparable to a small hotel gym. Property is in the owner’s basement, so there is some sound from upstairs as identified in the listing. Host stays out of your way but is there if you need anything.

Penny is an incredible host who really goes above and beyond! I greatly enjoyed my stay.

Mark was a great host and I enjoyed my short respite at his location. Everything felt clean and new and was designed with thought and care. The outward facing garden was lovely to look at in the morning and while heading to bed. Thank you so much Mark for such a comfortable stay.

Had an amazing stay here! Bob and Beth were extremely responsive hosts and provided a lot of clear instructions on how to find the carriage house. It was very clean and spacious and had a great coffee set up. The surrounding gardens are so lovely! Was quiet and walkable to the local downtown area

Highly recommend Ann’s place! We traveled with our toddler, and it was perfect for him. They supplied a pack and play and tons of board books. My only thing to note is that the walkway to the space is not paved so be aware with small children and suitcases.

John and Adam were excellent hosts. There were very responsive to my questions and issues. I loved the grounds and very well stocked kitchen. I would gladly stay there again.

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 could not be more perfect for our trip to DC. It was the perfect distance to the metro. Our group of 8 had so much space of our own, yet plenty of room to be together in the common spaces and not be on top of each other! We went in the coldest month of the year, so unfortunately we didn’t get to experience the best of what the outdoor areas had to offer but the views were breathtaking regardless. Melanie’s place was extremely clean and everything was provided and then some! Everyone in our group would like to go back in warmer months to spend more time outside. Before we got there, Melanie explained that there was an issue with one of the sinks in the cabins and said she would credit us accordingly. I thought that was great! It did not hinder or create a problem whatsoever! I hope we get to make it back sometime!

WOW. This was one of the most wonderful homes we’ve ever stayed in. Everything was clean, comfortable and accessible. Marissa was so helpful with recommendations, flexible check-in times so we could get my little one down for a nap, my three-year-old love the pool, dedicated playroom, toys, swing set and s’mores that were such a perfect gift from Marissa. My son asked if we could move there! My husband and I loved the kayaks and pond. We saw bunnies in the morning - it’s truly magical. It’s so private and just 2 mins away from town. We made so many memories and I can’t recommend staying at this property enough.

Staying at Shawna and Keith's cabin was a wonderful experience. Peaceful and serene, it was relaxing just to wake up in this private oasis. Shawna and Keith were very friendly and easy to get in touch with if we had any questions. They even provided items for some of the activities we decided to try while staying there. The cabin was clean, quaint, quiet, well-equipped; and looked exactly as described. We would definitely return for another weekend getaway! Thanks again!

What a gem! This cabin hidden in the woods is a perfect getaway location! The cabin itself has great heat and A/C (I got to experience both over 3+ weeks!), excellent hot water pressure in the shower, and the most comfortable bed! In addition, it's fully equipped with everything you could possibly need! Beyond the cabin, the woods are so peaceful, with deer, foxes, squirrels, and badgers! The dogs and I loved our multiple walks per day with not a person in sight. To top it off, Ted is the nicest host I've ever had! So wonderfully friendly and responsive. I hope to stay here again soon!

I recently had the pleasure of staying at Alexander and his wife's charming cottage, and we couldn't be happier with the experience. From the moment we arrived, Alex and his wife were incredibly accommodating and helpful, ensuring we had everything needed for a comfortable stay. The cottage itself was cozy and well-maintained, offering everything we required for a relaxing getaway. One of the highlights of our stay was the breathtaking sunset views. Watching the sun dip below the horizon from the dock was simply mesmerizing. The location is also ideal—just a short 10-minute drive to downtown St. Michaels, where we enjoyed exploring the local shops and restaurants. The hosts truly go above and beyond to make their guests feel welcome, and it shows in every aspect of their hospitality. I highly recommend this place for anyone looking for a peaceful and memorable retreat.

What a joy of a stay. The host is so incredibly welcoming to their beautiful property. It was exactly what you need for time in St. Michael’s. We would absolutely stay here again.

The house was beautiful and made us feel right at home. Having a washer and drying was also game changing and allowed us to be pack lighter than usual. Overall it was a wonderful stay and I will definitely be coming back!

We loved being in the woods and right by the river. Access to kayaks was a big draw. The home was comfortable and had everything we needed. We also loved being just a quick drive to Chestertown.