Cottage holiday rentals in Annapolis

This is a great location. We found this in hopes that we could get all our fishing boats in and accommodate everyone. Very nicely decorated and appointed with deck table seating for 14 a nice fire ring and jacuzzi. Host was fantastic great communication and can’t wait to see what they do with the other building on the property.

Overall a great place. It's only a short 10-15 minute walk on sidewalks to the rest of Eastport and the Annapolis harbor area, but in a quiet neighborhood that isn't busy with vehicle or foot traffic so it was easy to enjoy the lovely garden and patio outside with minimal city noise. It is accurate as described and from the photos. Did not experience any problems in the neighborhood or feel unsafe.

He was a great host and the neighborhood was perfect for us with little kids ! We had a wonderful weekend away!

I book this place for my bday I just wanted to have fun & have a break from routine but at the same time feel comfortable like home, and that’s how it was and better we all had a great time. Really nice property, fabulous decoration, great surroundings to visit, and nice backyard to relax and enjoy. The jacuzzi and fire pit unforgettable part of the trip, really nice atmosphere. If there was an issue super easy and efficient way to respond to the situation. Made my bday really special for me and my family <3

Great home in a beautiful area. Spacious rooms and the whole house is equipped with everything you need. I love Airbnbs that feel homey and not ‘commercial’. The area is BEAUTIFUL and walkable with great restaurants near by (checkout limonchello and get the pizza!). Perfect for a weekend.

Great place in a cute area!

This cottage was a gorgeous place to relax with my wife for her birthday. The proximity to the bay cannot be beat - especially since she made kayaks available for our stay. I would happily re-book next time I am in the area.

Beautiful waterfront setting. Two kitchens (one in each cottage). This property lacks privacy on one side, with an open view into the neighboring yard. While there's no fence or natural barrier separating the two spaces, the neighbors appeared friendly and unconcerned about the presence of visitors. Would recommend or stay again.

We stayed at Richard's house for 3 nights in late Spring. Its an amazing place, with great views from the rooms. There were lots of great places to see nearby.

The cottage looks just like the photos. Very quiet and peaceful location. They provided a binder that catalogs anything you may need during your stay. EXCELLENT communication. Easiest Check out EVER. Would certainly book again if we return to the area.

Absolutely wonderful stay! Josh and Judy were excellent hosts—friendly, responsive, and made everything so easy from check-in to check-out. The cottage itself was the perfect amount of space for our visit and had everything we needed for a comfortable stay in the DC area. The location couldn’t be better! The neighborhood is incredibly safe, and we loved being able to walk to so many phenomenal restaurants nearby. Having access to the garage was a huge bonus and made our trip so much more convenient and enjoyable. We love Alexandria and can’t wait to stay at Josh and Judy’s cottage again during our next visit. Highly recommend!

Beautiful setting. Very cozy house that was well appointed with everything that we needed for a longer stay. I was able to cook full meals in the kitchen with ease and my husband grilled one night. Other than that, there are local restaurants to enjoy as well. During the day my boys had fun fishing and being out on the water and the sunsets over the lake was definitely worth sticking around for. Unfortunately I had to work during the majority of our stay but I was able to do that seamlessly with the desk and reliable internet connection. Overall we had a great time at Miss Kitty’s Place and would love to stay there again someday.

Easy communication, accommodating, overall good experience. Very nice and quiet area.

We recently stayed at this beautiful Airbnb tucked away on a secluded property in Oxford, and it was exactly the reset our family needed. The house was spotless, cozy, and surrounded by nature—offering the kind of quiet you don’t realize you’ve been craving until you hear it. What truly made this stay exceptional were the hosts. We arrived by boat at a nearby marina, and due to our boat’s deep draft, they picked us up to bring us to the house. That extra effort made all the difference, especially with a group that included kids and family coming in from different ends. The home felt like a retreat—private, peaceful, and welcoming. It gave us a much-needed chance to reconnect, recharge, and create some lasting memories. We’d absolutely stay again and recommend this home to anyone looking for an escape from the hustle without sacrificing comfort or kindness.

Susan’s place was perfect for my parents’ extended stay with beautiful views of the Chesapeake out the windows and access from a lovely beach. My dad felt right at home going for his daily walks and meeting all the dogs in the neighborhood. The location is super convenient to a grocery store and selection of restaurants as well as getting into downtown Annapolis. The kitchen is well equipped and beds are great. Susan was incredibly communicative and very accommodating in extending the stay beyond their original booking.

This place was conveniently located near the central North Beach area! About a 2 minute drive or a 10 minute walk. The place was very quiet and peaceful. It had all the basic amenities and needs for our stay with baby daughter.

Our stay at Tiffany’s was just what we needed! A small cottage with just the right amount of room for our family, with a walkable neighborhood filled with charm and steps away from the bay! The screened in porch was heavily used for lunches and afternoon naps! Everything you could need for a family with small kids (mine were 4 and 19 months) was included too! While nothing in terms of food within walking distance, everything you needed was 5-10 mins driving and was not bad - good selection of restaurants too. Was very happy with location for a quiet secluded getaway, which now leaves me dreaming of a future retirement home in this area! Thanks for sharing your family home with us Tiffany!!

What an absolute treat to stay at the Cottage at Whitehall. We had such a lovely time, we stayed an extra day! Ty & Susie are gracious hosts and we were so excited to get a tour of the mansion and explore the grounds. The private beach at the back of the cottage is phenomenal, please take the canoe out - or even go for a swim. The sand is silky and soft, it was like a giant swimming pool nearly all to yourself. My husband enjoyed the canoe immensely (the waves scare me, so it wasn’t too much for me / but if you canoe out on the Meredith River it’s much calmer). If you fish - bring your fishing gear!! (Check local laws first, of course) Absolutely do not hesitate to book here if you have the chance, highly recommended 😍

Wonderful location. Excellent accommodations. Been there a few times and each visit has been most pleasant.

We visited Rock Hall for the triathlon this past weekend. Bob's place was perfect being within a couple miles of the starting point. The host was fantastic to communicate with. Would stay there again.