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 accommodation was perfect for our family event. The host even saw that we had an infant and provided a pack & play to help us out. Spaciousness, cleanliness, amenities and attention to detail are a few of the pluses for this rental.

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 home with lots of amenities in a lovely area of downtown. Walkable to shops, galleries, restaurants and historical locations. Private backyard to enjoy with morning coffee or evening wine. We’d definitely return!

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!

Really well appointed, beautiful peaceful waterfront location, everything well thought out, yard games, swing and kayaking super fun for kids.

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!

Dawn was so friendly and easy to communicate with! The apartment was great, 3 floors with a nice communal area, perfect for a weekend trip with friends! 2 great spacious bathrooms, and great light in the bedrooms. Desk on the 3rd floor was helpful for getting some work done. The deck was amazing for the brief time it was sunny!! Thanks so much Dawn, my group and I were so impressed with this place!

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.

This was our second visit to Paul & Erma’s. It’s in a perfect location for us to visit our son and family in Dover. It’s also very quiet with very little traffic. We especially love the swing, we sit out there in the morning enjoying our coffee and the company of their friendly little gray cat “Smoky.” We couldn’t ask for a better place to stay, it has everything we need. We look forward to go back in the future!

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.

We loved our stay here! The place was super walkable and area surrounded it was so cute. The place itself was really nice and clean, we especially loved the balcony! Will definitely be coming back!

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!

Jordan was really great from beginning to end.

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.

The apartment was spacious and had everything I needed to feel comfortable. However, the apartment has a lot of smart features but they all weren't usable. For example, I tried to raise some window shades but some wouldn't budge (like the family room shade and the master bedroom middle shade panel). The TVs were hard to control as well. Oh, and if you can't sleep with noise... the master bedroom windows are not soundproof or even near it. I was okay with the noise but my partner was not and had to sleep in the living room. Despite all that, I liked my stay. The location is in a great area & Raphael let me bring my cats (super grateful about that)! I'd recommend his place to anyone.

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!!!