Search Vacation Homes in Chestertown

"The house was exactly as promised! We were very happy with the accommodations!"

"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"

"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."

"Beautiful property, both inside and out, which was comfortable for two families with numerous children. Hosts were kind enough to make amenities beyond the usual available, including yard games, fishing rods, fire pit, and bicycles. We were VERY comfortable throughout our stay and were appreciative of everything this charming house had to offer. Three out of the four bedrooms had enough space for a crib, and the last still had a queen size bed that fit perfectly in the space with room to move...

"The house is located on a quiet street and is exceptionally clean. All of the essentials were provided and hosts Mike & Lena were very helpful and responsive. A great little place to stay!"

"I stayed at this property for a family wedding this last weekend with 5 other adult family members. The original spot we booked fell through last second and I found this unique property. It fit our needs perfectly. There was plenty of space. Everything was clean. The outdoor sitting areas were an added bonus. Plenty of parking. And the location in relation to downtown were perfect. I’d definitely stay here again."

"Super close to all downtown amenities. Would definitely return."

"My friends, our wives, and kids loved our stay. Everything exceeded expectations. We especially enjoyed the backyard where we played yard games, grilled, and enjoyed the river."

"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."

"Had a nice stay. We would definitalty book again."

"What a delight to have found this property. Beautiful drive to get to the Eastern Shore. Rock Hall The beautiful place that’s tucked in along the Chesapeake Bay. My fiancé and I needed a much desirable getaway. The bungalow at this property was the perfect place just for us to forget about our worries back home. The owners were kind enough to message us. Let us know if the events that were happening in town but more so anything that was happening on the property they gave us just a heads up as...

"I couldn’t have found a better place this gave us a great nights rest every night. We had a lot planned and all turned out great. Our first night we didn’t stop to eat so we asked Jimmy where we can go he directed us to a great Chinese restaurant. We were right smack in the middle of all our plans. Friday night An Inner Harbor Dinner Cruise. Saturday night a Kenny Chesney Concert. Sunday a Bowie Baysocks game and Monday on our way home stopped at the B&O Railroad Museum. What a great time thank...

"The pictures of this property don’t do it justice AT ALL. This house is amazing!!! It’s so cozy, spacious and stocked with so many amenities. The host was amazing to communicate with, the location was great and quiet. I could really go on and on about this property. I can’t wait to stay here again! Loved it so much!!"

"We have stayed in this neighborhood before on a previous visit, we enjoyed how quiet and friendly the neighborhood is. We will definitely visit again. The house is very, very clean, cozy, and well stocked with all the supplies you could possibly need. We enjoyed sitting out in the evenings and watching the stars!!! Thanks for making our visit complete!!!"

"We are from NY and had a major surgery at Johns Hopkins. Miller's Cottage was the perfect location for us to spend the week post-op prior to returning home to NY. Miller's cottage was clean, comfortable and very well equipped. There was outside seating which allowed us to enjoy the fresh air while recovering."

"We had a family reunion in the area and my brother, and I and our spouses spent 4 nights. It was a perfect fit for our needs. Extremely clean and well appointed. Even the coffee was great. Thanks so much."

"Beautiful historic home"

"This was such a beautiful cottage with the most picturesque garden in the backyard. The pool was an added bonus! The house is very quaint, beautifully decorated, and well designed for maximum usage of the square footage. If you are tall, you may struggle a little with the downstairs bathroom though. It was a serene getaway but close to absolutely everything downtown Annapolis has to offer. You can literally walk to restaurants and attractions!"

"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"

"We found the house as described and the location was excellent. We had some questions for the owner and he was responsive and helpful. Definitely a historic home. Really enjoyed the outdoor space."

"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."

"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"

"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...