Gorgeous cottage with to die for views and charming, well maintained grounds. Will come again!

Awesome place. My family had fun.

We booked a short mid week stay to “get away” for a family get together and what a perfect place! Stunning views, beach house nautical themed throughout and absolutely stocked with anything you could possibly need. The attention to detail was beyond anywhere we have stayed. Comfortable beds, detailed instructions and where to go binders and Jared was responsive to all questions. The kitchen is the best stocked I have ever experienced with a rental. We loved the area - peaceful little harbor town- and the residents were so friendly. We fished off the dock, kayaked and had bonfires at night. It was a perfect trip and a much needed, serene get away for all of us. Thank you for sharing your beautiful home!

We have stayed at Cliff Point many times and always feel right at home there! The views are beautiful, the home is inviting, and it’s always so wonderful to have quiet time with family! Even on a rainy weekend, we thoroughly enjoyed our time there! Thank you, Jared!

Such a wonderful property! You can really tell that the owners put a LOT of care into making sure it’s as enjoyable as possible for their guests. House was clean and well stocked. The use of outdoor items was a serious bonus and ensured we always had something to do. We would definitely come again and highly recommend to anyone else. Side note, it’s obvious an artist lives here which made for such a beautiful setting. 😊

The property has everything that we needed to relax and enjoy our stay. It is clean and beautiful. The host Jared Miller is very flexible, responds to and accommodated our request when he can, had thought of every detail and everything needed. We have been there a few times before, we love it, we will be back.

My husband and I and our 2 dogs took a long-needed break in February. The house, amenities, location and weather were perfect. The constant calming views of the water and walks down to the Cliff City boat ramp each morning and evening were just what we all needed. The location is peaceful but provides easy access to Chestertown, Rockhall and other points.

Perfection

4th year in a row we’ve stayed here as a group of 8. Perfect layout of seating, sleeping and accommodations! We’ll be back again!

This is a great house to gather with multiple areas to relax. We enjoyed the fireplace! The views are outstanding. We witnessed one spectacular sunrise and several sunsets. Chestertown is a cute, historic town. This was our second time staying at Cliff Point Retreat and we will probably be back!

Thanks for sharing this amazing place. It was a perfect place for our family holiday. The beauty and serenity is unique, ducks, geese, river, bay - always a part of the view- nature at its best. Merry Christmas!

Sunset views are spectacular from this waterfront gem. The house is spotless and extremely well stocked both in kitchen and outdoor equipment. Owner communication was top notch.

Such a perfectly designed space! We were happy with the seating areas, the outside area, and of course the views. We loved the fully stocked kitchen- thank you! The sea glass collection was beautiful, allowing for reflection and mindfulness. We look forward to our return!

We always enjoy staying! The views are stunning. You can see sunrise and sunset from the dock.

Extremely well stocked home with beautiful view. Great area for walking or biking. Quiet with an awesome deck and pier.

My group and I have been to Cliff Point Retreat many times beginning in the 1990's. There must be a reason. Many, actually. The house of three/four bedrooms with great mattresses, three complete bathrooms, full, well equipped modern kitchen and located dead on one of the widest points on the Chester River is simply spectacular. A beautiful "L" dock extends into the river (fishing or crabbing anyone?) and will accommodate your party as it sits to view sunrises and sunsets. Perfectly quiet location on a near dead end road. The VRBO listing will list details amenities. Jared Miller manages the property and is a gem to work with. Go to Cliff Point Retreat. You won't regret it.

We love to come here. There are so many extras. It feels like home away from home. Jared is a terrific property manager. He is very responsive and provides excellent details about the property. Everything was perfect and we will be back.

Beautifully appointed home - clearly the owners care very much about their property. Tastefully decorated. Everything is in tip top shape - inside and out. Super clean. Nothing is lacking - everything you need is here. Jared - the property manager - is very responsive. Peaceful, quiet neighborhood. Thoroughly enjoyed our stay. Thank you!

This is our fourth time staying at Cliff Point and we can’t wait to come back. We enjoyed the beautiful sunrises and sunsets, and how comfortable we feel in this home.

We had a wonderful time at this place. The house & view was spectacular!! We will definitely come back again!

The property manager Jared, is the best at answering questions, adding helpful information - the best! We have vacationed at this amazing property, we love it so much we have returned on 4 vacations! The kitchen is pretty much fully stocked if you like to cook during your stay, I did and loved it. Being a foodie and cook, I brought my own knives, thats just me! You can stock up the fridge at the grocery stores in Chestertown and be ready to cook crabs if you crab out front, we bring our boat. Our family loves taking the boat out to fish and crab, we had a bushel in 2 days! The beds are all comfortable and there are plenty of blankets if you need them as well as pillows. The bathrooms are stocked with things you may have forgotten - love that. The game closet is great, the kids loved it - old and young! The views while sitting at the dining table are amazing. The boat ramp is just down the road for easy in and out. I used the gas grill one night to cook chicken - oh baby, the grill is great, I need a new grill like this one : ) Thanks Jared for keeping this property a gem - close to perfection.

I am adding to a long list of positive reviews. The property was perfect for our family to gather. The place was clean and well stocked with everything we needed. The grounds, deck and outdoor toys - kayaks, paddle boards etc. made the trip fun and easy. We even did some crabbing! Jared was helpful along the way and we appreciate the opportunity to use the space. The location was the right mix of private and accessible -15 min to a nice town with an amazing bakery!! We hope to return again soon! Heather

We loved our time at Cliff Point Retreat. The owners had every amenity you could think of and then some. Even down to the showering products and q tips. The kitchen was fully stocked with every pot, pan, dish and seasoning plus storage containers. Our kids loved using the kayaks and we brought our fishing gear. The 7-11 in Chestertown sold bait which we needed a lot of because we easily caught 70 fish during the week. We were able to swim half the time as the jellyfish came early this year. There were tubes and floats all in the garage. Also the beds were the most comfortable I have slept on in any rental! I could go on but we would absolutely stay again.

This outstanding quiet property sets the stage for an amazing family vacation. It has EVERYTHING you could want for a relaxing stay and dreamy fun on the river. We lived on the dock from morning coffee to sunsets, enjoying the kayaks & paddle boards, fishing, crabbing, meals and more. The house is equally well appointed from comfy beds, ample seating for everyone to stretch out & a fully equipped kitchen where we made all but one meal for 11 days. Loved the grill too. Fast internet and quiet workspace for our son that had to work during the day. Seriously - it exceeded my already high expectations from the listing and reviews. Excellent communication. Absolutely Perfect! Still smiling.

My husband and I love this property so much which is why we have rented it multiple times. The view is unbelievable, it is quiet and private. The house itself is ultra clean and fully stocked. The property manager is beyond helpful and a pleasure to deal with. We look forward to our return next year.

Gorgeous riverfront property with amazing sunsets. Dog friendly, spacious rooms and fully stocked kitchen. Plenty of water sports -kayaks, paddleboards- to keep busy. Great restaurants-highly recommend Luisa’s. We will return!

This is the most beautiful and serene vacation spot we frequent. It’s so quiet and peaceful. The accommodations could not be better!

Great places nearby, however you don’t need to leave the property. Everything you could possibly need is available.

We’ve been coming here for a decade and will return every time we are in the area!

Friends and I love staying here year after year because it is a clean and efficient property, but an excellent home on the river with "things" to do -- both be on the water in kayaks or paddle boards or swimming, or relaxing and playing games or puzzles in the house, sharing meals, or heading into the quaint town of Chestertown.

Loved this property. The house was comfortable and well-appointed. Especially nice was the dock right on the water, where we could put out the fishing pole during the day and have a fire at the fire pit in the evening. There were birds nesting at one end of the dock, right near the honeysuckle, which was fragrant during our stay. There is also a picnic table which was perfect for our steamed crab dinner (we called Clark's Seafood, who steamed them ahead for us, and provided advice on how to eat them). Highly recommended property. We hope to come again.

We came for our sons college graduation weekend! The house is exactly as pictured… they have everything you can imagine from cookware to bug spray… if you need it it’s there! The lower deck on the water is very comfortable and the views stunning! We had a few people over for a luncheon and the house is set up for easy entertaining too! Highly recommend this gem on the Eastern Shore!