Historic Downtown Garden Oasis with Private Patio

Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond.

Very quiet area and well kept properly. The unit very clean and well kept, the Internet is pretty good with good reception, what I like the most was that it was so close to everything with restaurants and museums close by the park that hosted most of the events was close enough for a short walk and all sort of streets that held events were close by, this is a great location of the memorial day events and I have to say the honest were great and very helpful.

Very nice place. Great location, close to dining, etc. No TVs. Would have liked to know that going in. Otherwise, prefect spot.

The cottage was comfortable and welcoming. It was close to restaurants, the Farmers' Market and delightful shops and galleries.

A perfect stay in lovely, comfortable private guest quarters. Perfect for a couple. Well designed layout. Kitchen includes a toaster oven, microwave and coffee machine (capsules provided). Extremely well located, close to the superb Watershed Alley and Modern Stone Age Kitchen as well as the brand new Lawrence Wetlands Preserve (ideal if you are a birder!). Will definitely return to enjoy Stephen's and Marianna's guest suite.

The stay was incredible! We had an amazing weekend and definitely plan to return when we’re back in town!

We thoroughly enjoyed our stay at this property. The location was superb. We were able to spend the day in town with never having to drive anywhere. Chestertown was charming and unique and this rental went right along with that. Other favorites were the outside area, the layout and coziness of the rental. You will not be disappointed if you chose this as your rental for your Chestertown stay!

Wonderful location and amenities! Hosts were helpful and informative

Everything was perfect and cozy. Stephen and Marianna are wonderful hosts and have anticipated all of our needs yet again. Their rental is inviting and beautifully appointed.

Only wonderful things to say about this sweet apartment. First, the hosts, Stephen and Mariana, are incredibly hospitable and full of great ideas and recommendations for the area. This property is very clean and roomy (for two), has wonderful amenities and the hosts have thought of everything that makes this our go to place to stay when we are in Chestertown. This property is in a historic area, an easy walk to the river, the historic district, shops, a nature center, park, and many restaurants. It is an easy drive to anywhere requiring a car and parking is available and convenient. We highly recommend!

Perfect quaint property! everything you would need provided except we didn’t realize there was no TV but that was us not the property. Highly recommend. great location. walk to everything Chestertown.

Very neat and clean. Quiet and private. Short walk to shopping and restaurants. Quick response from host when questions or recommendations were asked. No TV encouraged us to enjoy the outdoors.

This is a charming place. Beautifully furnished with no detail overlooked. We loved the artwork by local artists, the attention to sustainability, and the commitment to the community. The location was perfect - a few minutes walk to the shops and restaurants and the Saturday farmers' market. One of the best we had ever visited!Communications with the owners and check-in were smooth. We hope to return.

Wonderful weekend in Chestertown - perfect location!

As others have noted, the space is very clean, well appointed and conveniently located. I'd like to add that the hosts have done a wonderful job of representing the community in the home. Their art collection is lovely and features local artists. The books placed are all interesting and about the area; even the chocolates were purchased from a locally owned store. I would absolutely stay here again and highly recommend it.

Loved the location and ease of access to downtown. Property was super clean, organized and beautifully appointed with original art too.

Very nice little apartment with a separate entrance from the main house. It was furnished and decorated very nicely (it didn't feel like a generic rental but it wasn't so fancy you were afraid to use stuff). Comfortable bed, nice pillows, nice sheets. I loved the porch and garden (and occasional visits from their very cute dog).

Weekend stay from Philly. Everything was perfect for the two of us. The space is so inviting with a beautiful outdoor garden and sitting area. Quiet, impeccably maintained and stocked with every detail that we needed. Outstanding hosts. Can’t wait to visit Charlestown annd stay here again!

Stephen & Marianna were great hosts! They gave recommendations for what was nearby for food and drinks and made us feel at home. the space was great and sitting on the patio was very pleasant. They are centrally located so it was very easy to park the car and walk to the main downtown. Would 100% stay again!

Your guest house was perfect. It had everything we needed. Short walk to town and the Chester River. Will definitely book again when we come to town for our son’s lacrosse games!

Property is clean & comfortable. Great location for walking to downtown Chestertown shopping and restaurants.

We loved staying at Stephen and Marianna’s fantastic home. The space is bright and well-decorated, it’s private and had all of the amenities we needed. The location is wonderful and we were able to walk a couple of blocks to the stores and restaurants and enjoyed the Saturday morning farmers market. When we checked in, the keypad wasn’t working but within about a minute, Stephen appeared and let us in so it was all very easy and nice. Highly recommend staying here - perfect for a couple to do a weekend getaway!

This is the second time I stayed here and will be back. I was able to work from here and enjoyed breakfast and lunch on the covered porch with a sweet companion (the owners' totally chill dog). Walking distance to everything. Check out the new wetland preserve at the end of the street.

We love this place and would stay here again in a heartbeat. Beautifully decorated with so many details and touches that make it extra special. Such a well done lovely property!!!

This property was so accessible to everything we wanted to do and the accommodations perfect for the two of us. It was like a home away from home comfortable and clean! Even the pillows were perfect! We would highly recommend.

We had such a sweet & relaxing stay at this garden oasis. It was equipped with everything we needed and we cannot wait to be back.

Short stay to move our child in to college. Our hosts were exceptional. The stay had everything you could want and the communication was great. We will definitely be back.

This is a lovely little place within walking distance to great restaurants, shops and points of interest. Our hosts were pleasant and available and gave us good recommendations for where to eat. This truly is a garden oasis outside. I sat with my coffee and wrote in my journal each morning on the patio. The inside is perfectly appointed with anything we needed and is super clean. We hope to return in the future!

What an awesome stay in Chestertown! We loved the little house that we rented! The owners of the property were very receptive and gave advice for dining options. The property was in walking distance of all restaurants, shopping and attractions. We would definitely stay again. Thank you!

Wonderful selection in Maryland Historic Cities circuit as well as in Scenic Routes on the MD Eastern Shore.