House holiday rentals in Annapolis

Leisa’s home suited our needs to a T!! We were in town to attend a wedding at the London Town and Gardens, which was just a half mile away. The rehearsal dinner in downtown Annapolis was also a short distance away. Everything was fresh and clean, the beds were comfortable, and the showers were really great. The lack of seating in the main room wasn’t a problem for us as we didn’t spend much time there during the day. The area around the pool looked really comfortable and inviting for guests staying during the summer season! Would stay there again.

Beautiful house and property, great location, and the host was super responsive. Hope to return sometime soon.

We had the most beautiful Thanksgiving gathering at Casey’s Porch on the bay for an extended family reunion. The house is lovely - spacious, gorgeous and cozy at the same time. The views on the water were amazing. There were plenty of beds and ‘hang out’ spots for our tweens and teens, and 3 private baths for the adult couples were much appreciated. And our hosts could not have been more helpful and friendly. Thank you for giving us this opportunity to make more happy memories together!

We had a great stay at this clean, comfortable, convenient and cozy house. We were impressed by the attention to detail. Every time we needed something, it was there. The kitchen was fully stocked and had everything we needed to cook our Thanksgiving meal. We were close to Annapolis And had an easy drive to the museums of DC. We took several walks to the nearby beach, and enjoyed both sunrises and sunsets. We would definitely come back! Thank you, Peggy!

The house/pool was gorgeous and had plenty of space for our large family! My only regret was not booking it for few more days!

It was simply amazing. Daniel was a fantastic host. The house was incredible. Spacious, beautiful and peaceful felt just like home. The family and I enjoyed every inch of it. Family vacation home for every trip we take to DC.

I stayed at Will’s property for four nights in March 2025 with a group totaling nine people. Upon arrival, we found the property clean and free of clutter. The property was conveniently located within walking distance to Union Market and the metro, allowing for easy exploration of the greater DC area. Will was an exceptional host, demonstrating prompt, friendly, and professional communication throughout our stay. Will graciously accommodated an early check-in and late check-out, which gave my party extra time to explore the DC area before our departure. I would highly recommend this property for groups of 5-9 people and would gladly return if visiting the area again.

The place was perfect, clean, homey, comfortable and really unique. Loved the pool, cold plunge, sauna, screen porch. We had everything we needed from fresh flowers and cookies to convenient multiple charging stations by the beds. Loved the outdoor lighting and overall coziness of this place. Quiet and peaceful, sounds of the water lapping the shore, beautiful place to drink morning coffee and watch the sunrise. Also found some great sea glass on the beach!! Love, love, loved staying here :)

Maggie’s house was perfect for our family getaway! You can’t beat this location. It was a quick walk to Eastern Market metro and tons of local shopping/dining options, yet the street was peaceful and quiet. We were able to spread out and relax as a family of three with two dogs. The house was comfortable and had everything we needed. Maggie was responsive and helpful from booking and through our stay. 10/10, would book again.

Robert's place is comfortable and clean. The mattresses are comfortable - firm with a soft top. He is friendly, responsive, and full of information about the area. We felt completely at home. It is the perfect distance from the mall. We took an Uber into the city each day and this was an easy, quick, and inexpensive ride.

We had a fantastic stay at Evan’s place. The cottage is beautiful and we really appreciated the lovely touches (fresh eggs, butter, dog biscuits). The property is beautiful and we enjoyed the calm waters of the bay and watching the ospreys. Highly recommend for a lovely and relaxing get away!

Nice place, had an issue with the ac but they had issues resolved quickly.

Such a lovely, comfortable home. Everything we needed. Loved the location. The neighborhood was extremely quiet and neighbors were friendly. There's a park with walking trails and lake half a mile walk away. The house was perfect. Relaxing. Comfortable beds and bedding. The record player was an added bonus, as were the puzzles and board games for the rainy days. Communication was excellent. Answered any questions quickly and was very helpful. Would definitely stay here again.

Our family had a great time - the property was spacious and clean, location was beautiful, and we loved playing outdoors in the open space and getting out on the water. Hosts were very responsive and everything we might need/want was provided!

Felt like home. Quiet neighborhood with walking distance grocery store. Extra amenities. Very clean and I’m a clean freak.

⭐️⭐️⭐️⭐️⭐️ Absolutely Perfect Stay! Our stay at Suitlamd Manor, was nothing short of amazing! From the moment we arrived, everything was spotless, well-organized, and exactly as described. The attention to detail—from the cozy decor to the thoughtful amenities—made us feel right at home. The location was perfect, close to everything we needed. yet still peaceful and quiet for a restful stay. Meka was an exceptional host, always responsive and helpful with local recommendations. We truly appreciated the little extras, like complimentary coffee and wine. The bed was incredibly comfortable, and we had everything we needed for a relaxing getaway. I highly recommend this place to anyone

Patti was an amazing host. She made sure that we had everything we need and she went the extra mile providing toys for our toddler. The house was beautiful. Very peaceful neighbourhood and you can just walk to the beach where you can find nice restaurants and a playground. Perfect getaway for families. And the heated pool is the icing on the cake

Several adult family members and I were in town for a wedding. Though we don’t live this way any longer, we grew up about 10min away from this house so are very familiar with the neighborhood. The house itself is tucked back into a residential area, but is on a main secondary road so be prepared for a little bit of fun getting in and out. Place was clean, spacious, and the host was very responsive to the one small issue we had. Keeping this place on the short list for future hometown visits.

- I wanted to have a nice getaway with my partner and couple friends since it was her birthday, this was everything I wanted and more and loved how comfortable and nice the home was. Will definitely be coming back in the future! Thank you Adam!

Tyler's place was perfect for our stay with our extended family. It's spacious and comfortable, with plenty of room to relax indoors and out. It has a very nice large porch and deck, great for some solitude or for kids to play. The beds were comfy and the linens ample, there are gorgeous large bathrooms and luxurious showers, the kitchen was well-stocked and included an amazing high-end stove, and the living spaces are nicely decorated and furnished with art and tons of books. One bedroom had lots of toys and kids' books, a very nice touch. Tyler was helpful, accommodating, and responsive. The location is very convenient to Arlington National Cemetery and within walking distance to a Metro stop. Everything about this rental was fantastic--we highly recommend it if you need a lovely space for a large group. Thanks, Tyler!

We really enjoyed staying here. It was a spacious home and we love the community. We were in town visiting family and It was so convenient being so close to family and friends. Very comfortable

The cottage /house was peaceful on the edge of an inlet from the Bay. The patio was lovely. It was chilly so we couldn’t use the kayaks. The kitchen was very well equipped. The dishes, utensils, cookware were quality. The extra cozy blankets were nice. He responded to a request very timely. We enjoyed the stay very much.

Schannette is a great and responsive host. A very homey-feel like accommodation which has everything you need, all kinds of amenities, (my kids love the super soft toilet roll😆) especially the kitchen. All you need is just pack your own clothes. Regarding the parking, backyard can bearly fit in 2 small cars only. But big enough for us to park a mini-van.

my family and I had an amazing time at Julia's place. She is an amazing host and the house was well furnished and we really enjoyed our 11 day stay there. look forward to coming back again.