Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities

We loved this place and hope to come back some day! The house is full of the cutest coastal decor and has everything you need to be comfortable and just relax.

Cliff Point Retreat has become our go-to destination for a peaceful, comfortable getaway. We’ve stayed here at least four times over the past four years, and every visit feels just as special as the first. The moment we step inside, we immediately feel relaxed and at home.The views of the Chester River are absolutely stunning, and the house is thoughtfully equipped with everything you could possibly need—even firewood ready for the fireplace, which adds such a cozy touch.Jared is hands-down one of the most responsive and attentive hosts we’ve ever worked with. He answers questions quickly and makes the entire experience seamless from start to finish.We truly can’t say enough great things about this hidden gem. We’re already looking forward to our next stay!

Our host Jared was once again, wonderful. Always responsive and a pleasure. The property is beautiful (no better place to view sunsets over the water) and is the reason why my college friends and I return almost yearly! Many thanks for a perfect stay!

This place is so so special - right on the water with the most wonderful view, so quiet and peaceful. They have fixed it up with everything a group needs for a perfect break. Extra thanks to Jared who was super responsive and willing to let us as an additional day at the last minute.

Always a beautiful stay with an endless view

The house and property were perfect.Pet-friendly is always a must for our yearly Dogcation and did not disappoint at this location. We surely will return next year.

Lovely stay as always! Appreciate the accommodations- clean and comfortable.

This house had everything we needed. Comfortable beds and pillows. This was our second time and we loved it.

My husband and I have rented this property more times than I can remember. We just finished a 2 week very relaxing stay. Peace and quiet!! We have already booked our 2026 retreat.

We have stayed here many times and will be back. Jared is a terrific host - always there if needed. The house has so many nice thoughtful extras. It is like home away from home. Plus, the location is ideal. It is on the water & private, yet close to nearby towns. It is one of the best VRBOs!

Very peaceful place. Loved it! Returning next year!

I love this property. It’s my third time back! Even in cloudy weather we enjoyed the peacefulness of the river, kayaking, and peaceful colors of the home. Wehad some canine visitors from the neighborhood which made it lots of fun.

Picturesque Lake Views! Gorgeous Sunsets!This lake house has so much to offer! Amazing water views! A nice sized grass yard with lovely landscaping! A wonderful dock with plenty of chairs and water activity equipment - kayaks, paddle boards, inner tubes, grills, so much! Our family stayed outside A LOT. This rental is well-equipped and well-maintained. Loved the décor! So many interesting things to look at. Large, comfy beds. The kitchen is well stocked. The great room is truly GREAT with plenty of places to sit and hang out. There’s a nice Farmer’s Market on Saturday mornings in Chestertown. Jared, the host, was great to work with! Friendly, informative, accommodating, and very responsive! Highly recommend and would definitely return!

Our 6th year at this property and we had a great time as always! We love the view of the water and spending time on the dock. The town is very cute and the Chestertown farmers market on Saturday is a must.

This property provides everything you need for a wonderful, stress-free stay. The kitchen was better appointed than my own! Linens were good quality ( bring a few extra bath and beach towels). Plenty of comfy spots for reading or chilling. The outdoor shower was a fun bonus. Highly recommend!

Excellent location. Exactly as described!

Property is serene, beautiful, clean, organized, and bucolic.Home is beautifully appointed with everything that a guest might need.The property manager, Jared, is outstandingly communicative, gracious, and prompt.

My sister & I were looking for a relaxing home by a river, and that's exactly what we got! The home had plenty of amenities and we were very happy. We:be already planned to return next year.

The property is clean, extremely well-equipped, and the water view is outstanding.

This place is amazing! From the moment we walked in we felt a sense of calm. The rooms are all decorated so nicely and very clean. The kitchen was stocked with everything we needed. The views are spectacular and the water toys so much fun - kayaks, stand up paddleboards, tubes, noodles, floats. The sunsets were beautiful. This was our first family vacation with our grandchildren (ages 2, 15 months and 12 months) They loved it. Thank you for sharing this slice of heaven with us.

Thank you again for hosting us. The property was wonderful. Beautiful dock and plenty of water activities!

Beautiful house and property. Well stocked kitchen. Communicative host.We thoroughly enjoyed our time here.Many thanks!!

Cliff point retreat was absolutely a perfect getaway experience. The home is loved and cared for; as is evident in the little touches too numerous to cite. It was well kept; decorated and located. Peaceful is a great way to describe it. We would love to return!

Cliff Point has been a wonderful place to return to.

This was a celebration for several different things and it was SO perfect! The house and amenities were top notch, the property manager was amazing to work with, and overall this was the perfect place to stay. We cannot wait to make this an annual tradition for our family.

Really great house: very clean, very comfortable furniture, and plenty of amenities. The owner has thought of everything, including little touches like binoculars. We loved all the decorations. The best part was sitting outside by the lake in one of the many areas to sit. We loved using the stand up paddle boards. This was one of the nicer rentals we have stayed at. I wish we had been able to stay longer!

Very peaceful and relaxing. Will stay again

We had a wonderful time at Cliffs Retreat. It was nice to be with family and enjoy the view. The amenities were great, and there was plenty of room for everyone.

Overall was an excellent place to stay!

This is our 5th year at the property. Have always been extremely satisfied with every aspect of booking, communication, amenities, etc! Plenty of room and comfortable for 8. We’ll be back again next year!

Great home that was very comfortable. Jared was very accommodating and overall a great experience.

we had a cosy time in the house, very nicely set up, well thought out and comfortable, good for family and friends, college kids and old friends. great for cooking, lounging, reading. everybody with their own chair and light, places to get away outside. our dog completely comfortable going from person to person. with plenty of bedrooms and bathrooms and extremely clean. the place has a gorgeous dock.we booked for winter, and didn't realize that we wouldn't be able to use the kayaks because of the winter winds at that part of the river, and that most of the water access is from docks rather than any coast line, as large stones have been placed in the Chestertown area to protect from erosion. that's why the 4 rating for accuracy of the listing. people more familiar with the area would have known. the location is a bit out of town on rural roads, about a 15 minute drive to Chestertown. the only thing missing was bike helmets but that's something either easily fixed by providing, or letting guests know to bring them. the host was extremely helpful and available, with every intention of doing whatever might be needed to make our stay pleasant. including offering to reimburse us for bike helmets if we could find some to purchase. the best VRBO host we've ever had, he was exceptional. all things considered we had a wonderful time there and would book there again.

Just what the doctor ordered. Waking up to the beautiful sunrise and enjoying a cocktail while watching the sunset were the highlights of our stay.

Absolutely beautiful location and property!

Beautiful property inside and out. Peaceful location

It's always a pleasant stay at Cliff Point Retreat!

the house was cozy and open and artistically decorated and furnished. the kitchen was well equiped. the views were amazing and the different outside areas (gazebo. deck, dock) were great. the huge trees were unexpected. the kayaks. SUP. and bikes were enjoyed as well as the beautiful sunset

My husband and I have stayed at Cliff Point Retreat several times and it never disappoints. Regardless of the weather, the water views are mesmerizing,

The house was very comfortable and had everything we needed. The amazing dock provided sunrises and breathtaking sunsets. We fished and crabbed every day. Our dog loved it! Thank you for allowing pets. We were able to decompress and relax

Great location and property. Our family enjoyed the experience and fishing on the dock. We caught several cat fish and was a enjoyable experience. Some good restaurants 15 minutes away. Only thing was we couldn't check in at 4pm because cleaning wasn't completed yet, but wasn't a big deal.

Perfect place for our reunion of old friends- 3 couples. -Explored the river and bay cove in the kayaks provided along with paddles and life jackets. -Caught crabs in the cages and rode bicylces provided. -So much space to gather for good conversation, meals, enjoying the water activity and especially the sunsets and stars. Hope to have opportunity to visit this beautiful piece of Maryland again.

Such a wonderful place to spend time with family. We had all we could ask for, plus such a beautiful view! This is our second stay here, but first time in the summer season. Such a treat to be able to enjoy the water so easily!

The place was clean. cozy, and well stocked for cooking and dining. We loved how the dock was set up and would have morning coffee out there, as well as dinner while watching the sunset. We took advantage of the kayaks, and at one time the kids had 5 kayaks out for a race around the nearby fishing shack and back. At night we were able to have a fire and make s'mores, followed by all the kids just laying in the dark at the end of the dock watching the stars. The home also had fun yard games stored in the garage, which we took out and played with. We tried catching crabs with our manual lines and their cages, but we didn't get any. We brought fishing poles with us and were able to fish off the dock - all the kids caught fish, though we unhooked and threw them all back since they were all smallish fish about 5 inches or so. I did snag a big fish when we went out on the kayak - alas, I was fighting for close to 10 minutes I think trying to reel it in until it snapped my line and taking my lure along with it. Maybe the next time were back, I'll meet the same fish again and have better luck.

There’s a magic to this place that keeps us coming back. We enjoyed our stay with our family and pups. The house is clean and well-stocked and the beds are very comfortable. Feels like a home away from home. Thank you again. We will be back!

We have stayed at this gorgeous property many many times and it feel like home away from home. Our pets have a blast. So relaxing and recharging. We already booked for 2 weeks in June 2025.