Holiday rentals with a washing machine 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. 🏥

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 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!

This is a small basement apartment in an older home. There is separate entrance, but you need to get the key from the host. There is a beautiful small garden where you can relax. The host is a very nice and gregarious person.

I enjoyed my stay! Kitchen, full bathroom, comfy bedroom, and workspace for a great price. Definitely recommend :)

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..

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.

our AirBNB stay was lovely! our host was incredibly flexible with our stay and communicated very frequently with us when we had questions or requests. it was located in a very walkable location close to plenty of restaurants, coffee shops, national aquarium (30 min walk), and little italy (40 min walk). check in was simple and checkout was even easier (only had to take the trash to the bin unlike some other complicated host requests). would stay here again!

It was a lovely home that was well situated near DC, Annapolis & other coastal entertainment areas. We especially enjoyed the peaceful neighborhood & many nearby walks with gorgeous water views. Having a king bed ensuite & 1.5 additional baths plus a fenced in yard for our dog made our stay most enjoyable. We would certainly stay again when next in the area.

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.

Perfect little house for a relaxing stay in Rock Hall. Close to the water and a quiet neighborhood perfect for walking in the morning or evening. Melissa sent so many great recommendations - great host!

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!

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!

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!

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

We had a great stay in Annapolis and the place was very instrumental in making sure it was that way. The place is well located, clean and consistent with the description in every way.

Had a great stay at Shea’s place! The street was quiet and quaint, and having a designated parking spot was very convenient. It’s in a great location. Walking distance to lots of restaurants, bars, and shops. Shea was great with communication, responded quickly, and was really accommodating throughout the stay. Would definitely stay here again!