House vacation 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!

Great place, nice atmosphere and big with a lot of rooms. Clean and lovely surroundings. I just wish with how big it is, there’s more bath rooms. Hope to come back when its not cold so pool is not cold. 👍🏼

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.

The property is everything as described and more! We immediately felt at peace and appreciated the wonderful amenities (fully stocked kitchen, sauna, comfortable beds, window views). Duane was a ray of sunshine and incredible host. He stopped by to give us a history of the property and suggestions for enjoying nature. Our walks were relaxing and we enjoyed all the wildlife: birds playing in the morning, a groundhog running about, and busy squirrels. We would certainly stay again when in the area!

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 :)

Attention to detail both architecture and a fully equipped kitchen with spices etc Visually unmatched sunrise to sunset

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.

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

Quiet neighborhood, beautiful area. It's in a community, not close to restaurant's or activities. It's a great place to relax at night. Beds were comfy, great shower and kitchen area. Very spacious. Truly appreciated the accommodations on our late check in Can hear the family upstairs as mentioned but Hashim and family were quick to quiet down the kids in the morning, so not a problem. Would happily stay here again.

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.

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.

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!

Claudia's place was well-suited for a long-term stay, and the interior was both clean and friendly. We had a couple of minor issues come up, which Claudia quickly responded to. The Lake Ridge area is also very nice, including its proximity to walks around the lake. Overall it was a great stay and very grateful to Claudia for offering such a lovely place.

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!

Absolutely amazing house and location!! Our family had an incredible week spent enjoying the property & views, spending time watching the sunsets by the fire, and kayaking around the bay. It's a great spot to teach kids to paddle and our 7 and 9-year old both enjoyed learning on the still waters near the sandy beach. The property and house are both thoughtfully designed and have so many spots to relax, read, watch the birds, and take in the views - made it feel like there was never a reason to leave. We had an incredibly peaceful week and would love to visit again!!

What a gem! My daughters and I loved our week spent here. The home is a true beauty with all the charm of a seaside getaway. All of the amenities truly made it feel like home, and the kitchen is amazing! Everything was streamlined and easy, the host was wonderfully responsive, and the home had such a friendly, warm, relaxing feel to it. It was such a terrific experience through and through, I would highly recommend taking full advantage of this beaut!

Thank you for the amazing girls trip! We had an absolute blast. The house was just as described and matched all photos! We always felt at home and it was beyond perfect. Will stay again if we come back this way!

The house was comfortable, clean and quiet. It was exactly what I was looking for to participate in a nearby competition. There were minor issues that the host addressed quickly and we got back to our vacation. Would stay here again.