Vacation rentals with outdoor seating in Chestertown

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..

The interior of the house was spacious and very clean. The kids enjoyed the 3rd floor game room/movie room.

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.

Easy check-in, great location, bedroom each had a bathroom and a half bath downstairs. Very pleasant stay- we would definitely come back again.

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!

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.

From the first time we communicated to the final day of our stay at Pirate's Perch, John was a fantastic host. Very kind and helpful, even recommending local restaurants for us to visit. Thank you, John!

We had our girls weekend here and loved the location. Close to all the downtown shops and cute coffee shops! Loved this location and are looking at booking again in the future.

Great place to get away, cozy historic home with a beautiful rooftop patio. Lovely location to go out and explore, grab some food and drinks, or stay in with your favorite people and enjoy some fun in the sun. It would be nice to have on site parking, but a public park isn’t too far away to walk.

It's a much better place than what you see in the photos- I don't regret staying long-term-

Anne’s space is absolutely it. We went for a 2-day stay while in Baltimore & it helped me fall in love with the city all over again. She is SUPER communicational and even had light snacks available when we arrived. (banana,apple,yogurt,granola) this is the perfect place in between the city and urban-local Baltimore.

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.

The space was beautiful! The rooftop was my favorite, being able to read a book in the quiet. They always responded quickly and were so nice! They also saved a parking spot for us in the back which we didn’t end up using because parking was not an issue at all up front.

We really enjoyed our stay at Paul and Erma's place. It had all that we needed for a weekend get away. It was close to our destination and was perfect for just relaxing when we got back. We would definitely stay here again.

We stayed with Wayne and Kathleen for three nights and loved our stay. Its a cozy cottage that sits above a beautiful, whimsical garden. We actually bumped into Wayne a couple times - great guy who made us feel right at home if we needed something but didnt hover - the perfect balance! This couple has loaded this place with all the amenities you could ask for. We felt like we were staying at a upstate new england B&B. Highly recommended, we hope to stay again!

Wonderful host—I felt right at home. Had conversation prior to arrival and felt like I knew her very well before arriving. The view was spectacular I could have just sat on the patio and watched the woods and water all day. Was there for a school reunion so I had other activities that I had scheduled. This was by far, the best Air B&B experience I have had. Fantastic host, comfortable, and stunning scenery. I am going to try and revisit soon.

Lovely, especially the patio.

We thoroughly enjoyed our stay at Mandi's place in Chestertown. The location is perfect for walking to stores and restaurants in downtown Chestertown and to the Farmer's Market on Saturday morning. Furnishings inside and cleanliness were great--we were all comfortable and happy. Although we did not use it, the kitchen seemed to be well-stocked for cooking meals. The outdoor patio was great too. Mandi was a very responsive and helpful host. We would definitely stay there again.

Jordan’s place was absolutely wonderful and made our weekend family trip to Baltimore extra special. The kids had a blast with the arcade games and loved the TV setup! The location couldn’t have been better—super convenient for visiting the Inner Harbor and catching an Orioles game. We also enjoyed having some great coffee shops and restaurants just a short walk away. Jordan was incredibly accommodating and easy to communicate with. We did have one small issue, but Jordan handled it quickly and efficiently. Highly recommend!

Cherrys place was beautiful. It felt just like we were at home and is definitely somewhere we would visit again . Thank you for such a great experience . Happy holidays !

Loved our stay at Marie’s condo. The place was clean, well-stocked and cute. Comfortable beds. Unbelievable view of the water and State House. A 10!

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

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.

A beautiful location with plenty of room for two couples. Nice balcony and panoramic view of the historical Annapolis waterfront and state capital. Fantastic restaurants and attractions within easy walking distance. Super parking too!!!