Breathtaking waterfront home on the Chester River

We we're in town for an Alumni weekend and had the best stay here! Everything was perfect, we have MORE than enough space, and had a great time with all the games in the house - such a fun bonus. We're already planning our next stay here!

It was a magical Christmas Holiday at the Christmas Cottage on the Chester River. We loved every moment from sunrise to sunset. We never left the house but had family come join us for breakfast, dinner, gift exchanging and relaxing by the water. We can’t wait for next year already.

A wonderfully relaxing stay!This property is impeccably maintained both indoors and outdoors. The kitchen is thoughtfully stocked with essentials, and the bedrooms and bathrooms are modern, spotless, and feature beautiful views of the lake.The pool is deep and inviting, with ample lounge seating for relaxation (note: the slide pictured is not available for use due to insurance restrictions). The setting is serene, with hummingbirds visiting the garden and sailboats gliding across the lake—an ideal spot for a peaceful retreat.

The listing was exactly as described. It also was very clean and well stocked. It is probably the best stocked VRBO I have ever stayed in. The views were amazing, the pool was great, and we couldn't have asked for anything better. Peter was a great host and was easy to communicate with. He even provided dinner recommendations.

Every summer my family vacations with my best friend and her family. We have 4 adults and 4 kids in our group and we have stayed in a few OBX houses and a few Chesapeake houses. This home was our absolute favorite so far! The house is so tastefully decorated and clean, with amazing amenities! The sliding doors to the screened in sun porch were AMAZING! We loved feeling like we were right there on the water while enjoying family time. We brought a boat and docked right at the house, a super easy process. This was such an amazing perk to this property! Our host, Peter, was so kind, responsive, and helpful! He was attentive to any concerns or needs we had and also gave us many recommendations. We cannot wait to come back!

Beautiful home, peaceful & quiet with lovely lapping water sounds and bird chirping. Our family of 9 (6 adults/3 active children) enjoyed all the amenities of swimming in the pool/river, kayaking, fishing from the pier, enjoying family meals together, exploring the lovely town 5 min away with the shops and nice playground by the waterfront. Sunrise and sunsets are gorgeous! Management is excellent and responsive to requests, etc. Definitely 10 thumbs up!

We try to take an annual family trip that involves water activities. This house and property was the perfect spot for our family which includes young children.

Our group of two families with kids had a fantastic time staying at this beautiful home. The pool was wonderful, the views were incredible, and everyone had fun on the river, thanks to the paddle boards and kayaks provided (including kids’ kayaks!). We would happily stay here again.

Two years in a row we've had an incredible Memorial Day weekend at this house. Tons of room for everyone, the river views are fantastic and the pool area is very relaxing. Also helps that it's a very easy bike ride into Chestertown. Highly recommend this place.

The cool weather kept us indoors playing games, puzzles, drinking wine and eating great food we picked up at the farmers market. Took a while for the hot tub to heat up but it was wonderful.

We loved our stay as much as we did last year. We were there for 5 nights and celebrated Christmas with friends and extended family. The views from every room were spectacular. From breakfast to midnight snacks we enjoyed the river and the cozy stove while watching Christmas classics and playing all the games Santa brought us.

The house is beautiful, with a glorious glassed-in porch perched over the river. Ideal space for a family reunion. You couldn't ask for a better place on the river.

We can’t overstate what a great find this was. In addition to the lovely setting, the cottage was well equipped, the kitchen but also with games, art and craft supplies and puzzles for kids. We think in summer with the pool and river to enjoy it would be even better. We are grateful to the owners for being willing to share this treasure!

Great place and great stay!

We had an incredible stay at the house. The views from every room in the house were stunning . Stayed with family ages 3 to 89 and everyone was comfortable. Kitchen was wonderful and had everything you would need to cook and in perfect shape.We enjoyed being able to bring our boat and tie up to the dock. Chestertown is a mile away and has much to offer with wonderful shops and restaurants. Can’t wait to go back.

A very comfortable, very clean and family-friendly place. The amenities were great. Area is quiet. Beautiful view of the sunrise.

Great house. Perfect location. Wonderful host.

The house and property more than lived up to our expectations. We enjoyed floating the day away in the pool and kayaking in the morning. The kitchen had everything we needed to make dinner at night and the living room and screened in porch were comfortable to read and relax in the evening. Our family is already talking about coming back!