Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
3 bedrooms3 bathroomsSleeps 8
Popular amenities
Deck or patio
Dog-friendly
Toys
Barbecue
Free Wi-Fi
Air-conditioning
Explore the area
Chestertown, MD
River Arts Chestertown
Place, River Arts Chestertown
17 min drive
Chestertown Historic District
Place, Chestertown Historic District
17 min drive
Washington College
Place, Washington College
18 min drive
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
124 min drive
Rooms & beds
3 bedrooms (sleeps 8)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 King Bed and 2 Single Beds
3 bathrooms
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Toilet · Shower only
Bathroom 3
Bathtub or shower · Toilet
Spaces
Deck or patio
Kitchen
Garden
Dining area
About this property
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
The privacy of a waterfront home welcomes you to pause and enjoy the beauty of the Chester River. Water views from every window connects you to the flowing water and the expansive outdoors. The southern exposure welcomes spectacular sunrises and sunsets. Relaxation and inspiration is abundant in this buffer zone!
Located close to both Chestertown and Rock Hall, it is an ideal gathering space for families and friends with many activities available in the area. By boat, this energetic space is located near Comegy Byte, the Langford Creek and the Corsica River. There is a boat launch within 1/4 mile of the house and a boat slip at the house; water depth is 2.5 feet MLT. Fishing from the 70 ' dock does not require a license.
For outside gathering, there is a large deck by the water with tables for dining, a picnic table under the shade of a holly tree and a water view bistro table and pergola beside the house.
For cooking, you can enjoy our amazing chef's kitchen with single oven, dishwasher, and fully stocked with dishes and utensils, including toaster and coffee/tea bar. You can also cook outside on our gas grill or charcoal grill. If dining inside, you can entertain guests at our kitchen table/dining bar or enjoy the water views at our second dining table.
For relaxation and amenities, we have a fantastic living room and dining area with water views, full size washer and dryer, 2 TVs with Direct TV, high speed internet, books, games and more! We also have an outdoor fire pit and indoor fireplace for entertaining. Firewood is available for your use.
We provide kayaks and paddle boards for you to enjoy the water around the property. We also have bicycles for you to explore the surrounding landscape. A few crab pots are available to try your luck for the famous Maryland blue crab. Bring your own fishing gear to fish directly from our private pier!
Three large bedrooms. Entry level bedroom has a king bed with two single day beds. En suite bathroom with shower and soaking tub. Perfect for families with smaller children.
The second bedroom has a king bed and the third bedroom is a queen. Both have chairs for reading and large closets. One hall bathroom has full bath while the other contains a shower stall. Linens (bed sheets, bath towels and hand towels) are provided with the rental contract. Please contact us if you are interested in opting out of the linen rental during your stay.
Come and fall in love with this retreat; return often!
Keywords: Self-catering, one-story water front cottage
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The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Recyclables can be placed in the green containers in the garage.
Please also make sure that you have your cell phone and device chargers.
Please place trash bags in the large container at the end of the driveway.
Failure to complete these may result in a negative review from the host.
Important information
You need to know
Property # 294688vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Chestertown
Located in Chestertown, this holiday home is on the waterfront. The area's natural beauty can be seen at Chesapeake Bay and Wilmer Park, while Sumner Hall and Garfield Center for the Arts at the Prince Theater are cultural highlights. Larrabee Arts Center and The Mainstay are also worth visiting. Kayaking, power boating and sailing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Chestertown Historic District - 17 min drive - 19.3 km
Historical Society of Kent County Maryland - 17 min drive - 19.3 km
Garfield Center for the Arts at the Prince Theater - 17 min drive - 19.3 km
Washington College - 18 min drive - 20.0 km
Getting around
Easton, MD (ESN-Easton - Newnam) - 65 min drive
Restaurants
Doc's Riverside Grille - 42 min drive
Hardee's - 39 min drive
Ford's Seafood - 36 min drive
Chester River Seafood - 41 min drive
Admiral’s Club Beachside Bar - 40 min drive
Frequently asked questions
Is Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities pet-friendly?
Yes, this property allows dogs (limit 2 total).
How much does it cost to stay at Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities?
As of 31 May 2026, prices found for a 1-night stay for 2 adults at Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities on 17 Aug 2026 start from AU$522, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities?
On-site parking is available at the property.
What time is check-in at Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities?
Check-in begins at 4:00 PM.
What time is check-out at Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities?
Checkout is at 11:00 AM.
Where is Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities located?
Situated on the waterfront, this holiday home is within 12 miles (20 km) of Wilmer Park, River Arts Chestertown and Sumner Hall. Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland are also within 12 miles (20 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The house was immaculate and wonderful. Most comfortable bed we've ever had in a vacation home. The view was amazing. We loved the purple martins and other birds. The live plants in the house was a really nice touch and made it feel like home.
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.
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!
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!
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.
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.
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.
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!
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.
We enjoyed our stay at the Shorewood property. Everything was clean and the hosts were great at communicating and even left us a binder with additional information about the place and things to do around Oshkosh. There is a nice view of the lake right outside the property!
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.
We’ve been coming here for a decade and will return every time we are in the area!
Stacy H.
Stayed 2 nights in May 2023
About the host
Hosted by Jared Miller
I started visiting this general area over 35 years ago and was captured by the essence of a waterside community. I am a board certified holistic nurse, retreat leader, speaker and coach that embraces the concept of sea glass as a symbol of transformation ~ becoming stronger and more beautiful with winds, waves, and sand.
Why they chose this property
There is a unique aspect of the Eastern Shore of Maryland - it draws your spirit to the landscape, the water, the wildlife and the expansive sky. I love knowing that this space is literally connected to all others by the water - the Chester River connects to the Chesapeake Bay and then to the Atlantic Ocean and beyond! The Kent County area is rich with artists of all kinds, wonderful restaurants, local theater and sweet little shops. Having Washington College nearby is a joy with their educational and inspiring venues. After 30 years of ownership, I am still awed by the sunrises and sunsets from the house as well as the peace and serenity of the house.
What makes this property unique
The house is within 1/4 mile of a public launch on the Chester River. Watching or playing on the water and observing the watermen, boaters and waterfowl from the house and dock.
Languages:
English
Premier Host
They consistently provide great experiences for their guests