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.

Nice house, very secluded, lots of entertaining space, hot tub was great, back patio, fire pit, everything was great. Isaac was very communicative with all aspects of our stay. An excellent getaway.

This is our second time visiting and a perfect spot with everything we needed. Could provide more dish towels, paper towels, and trash bags but supplies were provided quickly upon request.

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.

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 place in a cute area!

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.

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.

Perfect stay for our little family! It was an easy walk to the metro where you could easily ride to all of the major attractions. The hosts were very responsive!

We loved the location! Perfect for a trip with our dogs. Loved waking up to the beautiful view!

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!

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.

We absolutely love Loon Cottage! It was our second Memorial Day trip to the cottage and it’s so special. We love the decor and they had wonderful toys and games for our 5 and 2 year olds to play with. The outdoor area is also so magical for golden hour bbqs and our city kids loved running around. Location is close to lovely Easton and all that the Eastern Shore has to offer. Thank you for a great stay, we’ll be back!

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 😍

This house is so relaxing and beautifully decorated. We were here in the end of May/beginning of June when all the plants were full and green. The outside gardens are so peaceful with bird feeders and bird baths. We sat and watched all the birds come by. The screened back porch with gas fireplace was our favorite place to hang out. We were so busy that I only used the sauna once but what a wonderful amenity. Very clean and very well stocked with everything you need in the kitchen. We loved this place!

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.

Absolutely incredible stay! This place exceeded all expectations. The view was absolutely breathtaking — one of those rare spots where photos just don’t do it justice. Super peaceful and perfect for relaxing or disconnecting from the chaos. Everything was spotless, thoughtfully set up, and cozy. I left feeling totally recharged. 100% recommend to anyone looking for a quiet escape with unforgettable scenery. I’d come back in a heartbeat!