Vacation rentals with outdoor seating in Chestertown

As I let MATT know this definitely would be my dream home. I will be back many times in the years to come as long as I’m out here.

Our second stay, and we can't imagine staying anywhere else when we are visiting family in Greensboro. The house and surroundings are beautiful and Cindy provides everything you could need.

This was the second time we stayed at Hannah’s in Chestertown. Simply put, it was wonderful. The house is charming and historic. Built in the 1700s but the kitchen is completely up-to-date and wonderful. The bathrooms are perfect and the linens are luxurious. It is spacious and welcoming with lots of little notes scattered throughout encouraging us to settle-in and enjoy everything. It is a great location for walking around all of Chestertown including the long river walk. We enjoyed breakfast around the generously sized kitchen island, afternoon tea outside in beautiful sitting area in the front yard and evening wine around the fireplace (gas logs) in the living room. We’ll definitely return again as Hannah’s truly feels like home away from home.

We loved the house and the location. We had such a great time and appreciated Liz allowing us to check in and check out at our convenience. We definitely recommend for a friend’s get away weekend. The house is so comfortable and well equipped. Location is fantastic, everything is walkable from this house. We lucked out for sure as the weather was also beautiful. Thank you Liz

Rob and Libby’s place was perfect! They are fabulous hosts who responded to our questions promptly to ensure we had a wonderful stay. We were extremely happy with the home; it was very bright and cheerful, along with having every amenity you could want. It is obvious Rob and Libby are proud of the home, from the quality and comfort of the furnishings to how it was immaculately clean. We were very comfortable in our “home” for the weekend. It was the perfect spot to sit and relax before going back out to explore Annapolis. The location can’t be beat – only 2 blocks from USNA visitor’s gate and the wonderful shops, restaurants, and pubs on Main Street and in the marina area. We would definitely stay at Rob and Libby’s again! Thank you for a great weekend getaway!

Carrie’s house was beautiful, peaceful and everything we were looking for!!! We will definitely stay there again.

We were very comfy at Tim's place. Back sunroom was nice for adults to chat after the youngest of us had gone to bed. Nice selection of coffee and spices, and kitchen was well-equipped. I was comfortable in the front bedroom even through the mattress was sort of firm (reminded me of hotel mattresses overseas.) Note that one bedroom lacks a closet but the adjacent bedroom has a large enough closet to share.

Really enjoyed the stay. Great location. Quiet neighborhood and short walk to everything you need. Grocery store, coffee shop, pickleball courts, ice cream and so much more.

Clean, quiet and welcoming. Ellie’s homemade banana bread was outstanding!

My wife and I have been going to Annapolis for years, usually several time a year, and staying downtown. Never again. We love Eastport and there is no better location to enjoy the local fare. Everything you could want is a nice, short walk away. As for the Bird's Nest, we couldn't have asked for a better space. Very cool decor, neat little patio in the trees, and the lighted yard and walkway added a little something special. We hope to return soon!

Dana’s place is just as described! Perfect location, beautiful views and well appointed. Dana was very responsive and accommodating. Highly recommend and would stay here again.

I would give this place 10 stars if I could! Charles and Ginny were fantastic hosts and incredibly helpful and accommodating. The room is perfect, very clean, well stocked, well maintained, and just an overall great place to stay. The stair chair was also perfect for my elderly mom. I highly recommend staying here and I look forward to visiting again. Thank you so much for everything, Ginny and Charles!

Convenient location in a quiet neighborhood. Walkable to waterfront, restaurants, and shops. Well-stocked kitchen. Bathroom is quite small. Kelly is a thoughtful and generous host, and knows how to make his guests feel welcomed.

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

We enjoyed our stay. Very comfortable bed and host was very responsive. We highly recommend staying here.

We enjoyed our stay. Loved the Church Bells. The location is perfect, walkable to everything you need. Deborah’s attention to detail and thoughtfulness was appreciated. She even had beds, bowls, & treats for the dogs.

We had a wonderful stay at Ellen’s condo. The location was ideal in downtown. Annapolis. The unit was very well appointed and filled with every supply needed. Spotlessly clean, comfortable, and a safe and secure location. The included onsite parking was a big plus. Highly recommend!

The place was perfect for me and my son. It was by far the nice place that we stayed at in Chestertown. We will be back again.

Fantastic studio and a good size. Location is perfect and on a quaint street close to everything. Place was spotless and well equipped. Highly recommend.

Very convenient and perfect for USNA events. Parking was easy. Recommend you stay if you have 4-5 people.

Jared's place is well positioned at a 10mins walk to the harbour but close to restaurants on Eastport too. Great location on the water near boats and view of wonderful spa creek. A cool appartment too. Jared is extremely responsive to any questions and communicates very well. A 5 star stay for sure, coming back!

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 beautiful views of Spa Creek through the huge windows in the newly updated condo. Fantastic location with parking onsite (you do not need to worry about street parking). The building is older, but the rooftop pool was a plus for our family (there was also a lifeguard on duty). Professionally designed space with thoughtful touches throughout. The king sized bed is very comfortable and there are blackout shades in the bedrooms. The second bedroom has two trundle beds that are a little squeaky, but our daughter enjoyed having her own space. Already looking for the future availability of this AirBnB! Highly recommend 😀

Our Annapolis trip was wonderful. My daughter lives in DC and my wife is from Baltimore. Annapolis was a great stay because it provided us easy access to both places while also having a lot to do in town. David’s place was cozy, conveniently located, and perfect for us! The noon check out was great too. The bed was comfortable. The bathroom heater was an awesome find (we are from Florida so the mornings were chilly). It was a beautiful location and we had a great time! Thank you for sharing your place with us and allowing us to explore Annapolis while visiting family!