Vacation rentals with a washer and dryer in Chestertown

My parents stayed while visiting my husband & I. They both commented on how comfortable the bed was and that the apartment was very clean. They also really appreciated the easy parking and how quiet it was. Plus close to Charles Village & Hampden. A great find.

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. 🏥

The place was beautiful and very well kept. John is a wonderful host and helped us to have a great stay. We enjoyed the vintage setting and locality.

Great above-garage apartment. Fully equipped kitchen, large bathroom, and comfortable king bed with walk in closet. Location is directly off the highway but not at all noisy. Had a little trouble finding the location (I accidentally drove past it the first time) but eventually realized I was at the wrong place. 10 minutes to downtown Annapolis.

Renee is such a kind and gracious host, she was so helpful and accommodating! The unit was clean and very cozy for my weekend stay.

We found this beautiful place when we needed a dog-friendy rental for our large dog while visiting our son at college. The rental is in a fanatic location, a very short walk to the waterfront and downtown Chestertown and its great shops and restaurants. The rental was immaculate and very comfortable. It had everything we needed. The backyard was more private than we thought and our dog enjoyed playing fetch in the back. The bedding was comfortable and relaxing. The host was very responsive and helpful. Great experience! Thank you!

We had a very busy Easter week with family and friends. We were able to relax to peace and tranquility for coffee/breakfast on the deck or end of day on the couch. Such a quiet neighborhood with water views, chirping birds and cooling breezes. We thoroughly enjoyed our stay and will be back again. Wayne and Kathleen were very accommodating but gave us our space! Highly recommend this property to anyone. Steve and Joanne New Hampshire

Joyce and Nicole are two of the nicest ladies you will ever meet. They are so flexible and welcoming. Their place is exactly as described and is so warm, inviting, and comfortable. We will stay there again and again when we come to town to visit my new granddaughter!!

Perfect location if you’re in Annapolis for a game or just to visit the city. Christopher’s house was the perfect location and distance from everything in the city. Also, very spacious and nice house perfect for me and my 4 other friends.

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.

Brandon was very responsive and his house was exactly what we needed for visiting DC with children and a dog. The drive into DC was easy and scenic. The house was clean, the fenced yard was great for the dog, the neighborhood felt safe with great water views for walking, and there were good restaurants on the water within short driving distance from the house. Overall it was a great experience!

This was a perfect home for a 60th celebration. The home was spotless, beds so comfortable, kitchen well appointed. Host left touches for guests to feel comfortable and welcomed. Quiet neighborhood, great backyard and close enough to walk to stores, resturants and Washington College. I would highly recommend this home for a familiy or friends get away.

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 a nice stay while in town for a wedding! Great for our families together with enough space for four families with children. We were very grateful for their accommodations in setting up some extra air mattresses for the children.

Second stay at this cottage, super clean and well appointed. Restaurant and community beach are within walking distance. Great spot!

Our stay was pleasant. The listing is in a neighborhood, but it was quite peaceful. Kirk and Diana had a book listing sites and places to go to for even the basic groceries. Every item needed for our stay within the house was listed and identified by location in their folder, as well as everything labeld nicely. Certainly worth the stay.

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!

The home was great. Very clean and a great location- right in downtown Annapolis. Definitely recommend this as a place to stay, and I plan to book again in the future!

everything was great! quiet, easy to find, and super responsive, kind host. very, very clean place!

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!

This property is in an excellent location in Federal Hill and is walking distance between the big stadiums and the harbor as well as great restaurants. The unit was VERY clean and well kept and we enjoyed an evening watching a movie with the great sound system and large TV. All in all - a fantastic stay!

We really enjoyed our stay! The place was clean, comfy, and had everything we needed. Jared was super responsive and helpful. I highly recommend.

Host gave an accurate description. Also, gave clear and easy instructions for checking in to condo. Had everything we needed. Comfortable beds! Would highly recommend if you're visiting the Annapolis area.

Stayed here for a long weekend to celebrate my daughter’s second birthday. Place is very kid friendly, the pack n play already being there was very helpful for us. Very walkable to many restaurants and bars. The bedrooms are a good size and the shower had great water pressure. Kitchen was beautiful and had everything we needed. Would recommend this place to family and friends and would also rebook again