Holiday rentals with a patio in Chestertown

Clean, tidy, enough space to cook, lounge, and sleep on comfy bed. Coffee and creamer with french press, Yay! Extra bedding. It was great - everything it should be. Light sleepers will want to sleep in the bedroom with the door shut. Pull-out bed sleepers should expect to hear every single word spoken by pedestrians as they walk past the window (bring earplugs). The Egyptian restaurant a few blocks away has a "dips" platter for around $10 (a GREAT value) that will serve at least 4 people and comes with 6 pita's.

This is our second stay in Megan’s place and I wouldn’t stay anywhere else in Annapolis! She’s the perfect hostess, fully stocked, having everything you can possibly need! She always responded quickly with any questions and follows thru on any needs! Thanks Megan! See you down the road! ☘️💚

Sophia and her family made us feel comfortable,safe and always a pleasure to talk with. Accommodations were just what we needed. A bright and multipurpose kitchen made it easy to make family meals after a long outing. An amazing Washer and Dryer Her spacious cozy bedrooms helped us to finish the day off with contentment. I highly recommend making the choice to stay at Sophia’s and her family’s place. ⭐️⭐️⭐️⭐️⭐️ Right next to John Hopkins Hospital. 🏥

This place is great, the nicest Airbnb we’ve ever stayed at. Location was fantastic, nice restaurants are nearby in the neighborhood(recommend Timber Pizza Co). Easy walk to the Naval Academy , DTA, and St Johns for the croquet cup. Kitchen has everything you need to cook. Appliances are high end and the TVs are nice. Highly recommend.

Exquisite. Right in the heart of town. Across the street from the backyards of captains row at naval academy. Amongst many historic properties open to visitors. The bed was like a super high end hotel. We LOVED this house and Annapolis. Thank you!

A great location for coming in to see a baseball game. We appreciated the parking pass (though did alot of walking since everything is so close). Surprisingly peaceful neighborhood yet in the heart of the city.

Beautiful place just steps away from all the best shops, restaurants and things to do in Annapolis! Hosts were communicative and responsive and the home was very well stocked.

I have stayed at this property before and it is always a great experience. Katie is a wonderful, responsive, host. The welcome basket and handwritten note are thoughtful details. I very much look forward to my next opportunity to stay in Katie’s house again.

This retro house was perfect for our friends weekend get away! Loved the quirky, interesting decor and cool layout! The beds ( the sheets in particular) were very comfortable ! Our favorite part was sitting on the porch, chatting before and after dinner. . Sarah was a great host making sure everything was good via messaging. Would be happy to stay here again the next we visit Annapolis..

This home is really nice! We stayed there because our daughter was getting married at a venue about 5 minutes away from the home. It was perfect! Plenty of space for our family and was great for the bridal party to get ready! Nice open floor plan. The beds a bedrooms were very large with comfortable beds. The home was well equipped. The outdoor area was nice and I’m sure the pool is nice in the summertime. Thank you for sharing your home with us on this very special occasion.

We had a great stay at Christopher's this past weekend! Christopher's home looks exactly as pictured, and is located in a fantastic spot to use as a home base to explore the rest of the city - easily walkable to a grocery store, pharmacy, and restaurants (including a delicious food hall!). We were very comfortable and greatly appreciated Christopher's hospitality. He even let us check-out late so that our baby was able to get a long nap in before our travel. We would happily stay here again if we return to Baltimore. Highly recommend!

We really enjoyed our stay at Kwan’s place. It was very clean and the beds, sheets, and pillows were so comfortable. It was super rainy during our trip, which was a bummer, but made us super glad that the house we were in was so awesome. Our daughter loved the swing set and slide outside and had a blast running around the house. Kwan was also very friendly and responsive via the app. Would definitely recommend this place to someone looking to stay near Annapolis!

Beautiful home with amazing hosts! always responded promptly when a question arose and was ready to help if we needed.

We were staying at another AirBNB which was not as advertised… I contacted Amoni about possibly staying at hers and she helped make sure we were able to! Her home was 4 bedrooms and three bathrooms! Everything was incredibly clean. She thought about everything! All of the small items you normally forget going away for a weekend is already there. As soon as you enter the home, you can smell how clean it is and how well taken care of. I would LOVE to stay there again!

Excellent time staying here. Courtney was courteous and very responsive to our needs. Definitely a must use if ever in the area! Thank you Courtney!

Had a really great stay for three nights at this lovely home in Edgewater. The house sits on a corner lot with wonderful views of the bay. The neighborhood is safe and cozy. Lots of friendly people out walking and enjoying the surroundings. Felt right at home. The house was clean and very functional. Eddie was great to work with and I would recommend this to anyone wanting a home base for the Annapolis and surrounding areas.

We had a great stay in Annapolis and the place was very instrumental in making sure it was that way. The place is well located, clean and consistent with the description in every way.

The host, Scott was very proactive in supplying instructions and very helpful. The place was immaculate and has many modern updates. Location was spot on for all things Annapolis. We would definitely stay again.

A great sunset view from the balcony, such a nice quiet river/bay beach, peaceful community to walk around. Would stay in again! Would note there’s 1 flight of stairs up as it’s a 2nd floor condo of sorts; and a big hill/stairs down to the beach. However, also a parking lot if needed to drive to the beach. Beach chairs were nice to have. There was no cooking oil but I think we left some :) I would only ask they replace the dining room chair with the hole in the seat. The pool was closed and that was not expected! Adam was very responsive when we messaged.

We enjoyed our long weekend stay in Chestertown. The Park Row AirBnB was exactly like the photos. It was clean, comfortable and was perfectly located in town and there was ample parking directly in front of the AirBnb building. We walked to everything the town had to offer. If you plan to book a stay, the town has a lot to offer in terms of art galleries and outdoor sculptures. And there is a wonderful craft/farmers market every Saturday morning that runs along the main street of town. It was fabulous! We had a very enjoyable stay!

We thoroughly enjoyed our stay with Kelly in her lovely, spotlessly clean Condo. Everything you need to make your stay a memorable one is on hand. Check in was a breeze, Kelly is supper friendly and very knowledgeable of the area. Great location for easy downtown access and lots of shops an restaurants close by. We hope to return.

Beautiful condo that felt like a home away from home. Easy check in and relaxing environment. Highly recommend 10/10.

We would definitely stay at Kimberly's place again. Super decor, very comfortable bed. Loved everything about the place and Kimberly was very responsive and helpful in every way. Great Place!

Nice place. I’ll be coming back for sure.