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

Photo gallery for Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities

Sunset from the house
Fully stocked kitchen with new countertops, stove/oven and coffee bar
Dining area immediately off kitchen. Perfect for happy hours and conversations.
View from kitchen island through property to first dining area
Coffee and tea bar

Reviews

10 out of 10

Exceptional

3 bedrooms3 bathroomsSleeps 8185.8 sq m

Popular amenities

  • Parking available
    Parking available
  • Washer
    Washer
  • Outdoor space
    Outdoor space
  • Barbecue grill
    Barbecue grill
  • Kitchen
    Kitchen
  • Air conditioning
    Air conditioning

Explore the area

Map
Chestertown, MD
  • The Mainstay
    37 min drive
  • Rock Hall Harbor
    38 min drive
  • Eastern Neck National Wildlife Refuge
    60 min drive
  • Easton, MD (ESN-Easton - Newnam)
    65 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

Property manager

Jared Miller
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

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A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM

Children

Children allowed: ages 0–17
Children welcome

Events

No events allowed

Pets

Pets allowed
If approved, pet deposit will be required

Smoking

Smoking is not permitted
Non smoking only

Important information

You need to know

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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
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

We should mention

A car is required for transport to and from this property

About the area

Chestertown

Located in Chestertown, this holiday home is on the waterfront. The area's natural beauty can be seen at Wilmer Park and Ferry Park, while Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland are cultural highlights. Hazel Miner Monument and Paul Reed Smith Guitars are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Chestertown, MD

What's nearby

  • Washington College - 18 min drive
  • The Mainstay - 37 min drive
  • Rock Hall Harbor - 38 min drive
  • Queenstown Premium Outlets - 50 min drive
  • Eastern Neck National Wildlife Refuge - 60 min drive

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 65 min drive

Restaurants

  • ‪Doc's Riverside Grille - ‬41 min drive
  • ‪Hardee's - ‬39 min drive
  • ‪Harbor Shack - ‬40 min drive
  • ‪Waterman's Crab House - ‬38 min drive
  • ‪Colosseum Pizza - ‬40 min drive

Frequently asked questions

Is Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities pet-friendly?

Yes, pets are allowed at this 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 Garfield Center for the Arts at the Prince Theater. Historical Society of Kent County Maryland and Washington College 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.
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Rating 10 - Excellent. 267 out of 270 reviews" "
Rating 8 - Good. 3 out of 270 reviews" "
Rating 6 - Okay. 0 out of 270 reviews" "
Rating 4 - Poor. 0 out of 270 reviews" "
Rating 2 - Terrible. 0 out of 270 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Peggi G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Peace and quiet
Beautiful property inside and out. Peaceful location
Stayed 2 nights in Oct 2024

10/10 Excellent

Angela C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Joyful and Renewing
It's always a pleasant stay at Cliff Point Retreat!
Stayed 3 nights in Sep 2024

10/10 Excellent

Jan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
50th birthday celebration
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
Stayed 4 nights in Sep 2024

10/10 Excellent

Ann F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
September Getaway
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,
Stayed 4 nights in Sep 2024

10/10 Excellent

Debbie M.

Liked: Cleanliness, check-in, location, listing accuracy
Relaxing Retreat
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
Stayed 7 nights in Sep 2024

10/10 Excellent

Erika M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location!
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.
Stayed 3 nights in Aug 2024

10/10 Excellent

Chris W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Old Friends Reunion
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.
Stayed 7 nights in Aug 2024

10/10 Excellent

Suzi B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful week with family!
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!
Stayed 7 nights in Aug 2024

10/10 Excellent

Brian & Monica P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful and relaxing stay, with full of of activities
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.
Stayed 2 nights in Jul 2024

10/10 Excellent

Emily K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Another great stay
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!
Stayed 7 nights in Aug 2024

10/10 Excellent

Cynthia S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise
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.
Stayed 8 nights in Jul 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing Oasis
This house has a beautiful, peaceful setting with a vista of sparking waters. The inside is welcoming with eye catching details. The dock is sturdy with lots of seating. Birds and wildlife abound! Just lovely.
Stayed 21 nights in Jun 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication
We loved the space from beginning to end. We had a problem with the ac and got a response and fix.
The property is lovely with coffee amenities, toy amenities and comfort galore. The landscaping is so beautiful and the water feature with comfortable and abundant seating is extraordinary. We had a lovely stay!!
Stayed 3 nights in Jun 2024

10/10 Excellent

Loni B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A little slice of heaven
Gorgeous cottage with to die for views and charming, well maintained grounds. Will come again!
Stayed 2 nights in May 2024

10/10 Excellent

Jingdi W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice
Awesome place. My family had fun.
Stayed 2 nights in May 2024

10/10 Excellent

Marylee M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful, Beautiful and Serene Family Vacation
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!
Stayed 4 nights in May 2024

10/10 Excellent

Hannah P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Trip to the Eastern Shore
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!
Stayed 2 nights in May 2024

10/10 Excellent

Laura K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect
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. 😊
Stayed 3 nights in Apr 2024

10/10 Excellent

ROSARIO O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Place, Perfect Host
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.
Stayed 3 nights in Apr 2024

10/10 Excellent

Ann F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
February Sojourn
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.
Stayed 4 nights in Feb 2024

10/10 Excellent

Margaret M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cliff City
Perfection
Stayed 4 nights in Feb 2024

10/10 Excellent

Ben G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great everytime!
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!
Stayed 4 nights in Jan 2024

10/10 Excellent

Christine A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
New Years Escape
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!
Stayed 5 nights in Dec 2023

10/10 Excellent

Chris W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Christmas on the Bay
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!
Stayed 4 nights in Dec 2023

10/10 Excellent

Katherine R., Madison, NJ USA

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely perfect
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.
Stayed 4 nights in Nov 2023

About the host

Hosted by Jared Miller

Host profile image
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
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