Entire home

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

A wooden deck with Adirondack chairs and tables overlooking a calm body of water at sunset.
A kitchen with wooden cabinets, a white refrigerator, a central island with wicker chairs, and a tiled backsplash.
A house with a dock leading to a grassy area with chairs.
A dining area with a table and chairs, a ceiling fan, and a view of the water through the windows.
A spacious kitchen with a large island, a dining area with wicker chairs, and a view of the outdoors through large windows.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Scenic water view
    Relax and unwind with top-rated water views, offering a scenic experience.
  • Garage parking available
    Enjoy the convenience of garage parking - a rare offering in the area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Patio
  • Dog-friendly
  • Toys
  • Barbecue
  • Air-conditioning
  • Garage parking available

Explore the area

View map
Chestertown, MD
  • Place, River Arts Chestertown
    ‪21 min drive‬
  • Place, Chestertown Historic District
    ‪21 min drive‬
  • Place, Washington College
    ‪22 min drive‬
  • 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

Add dates for prices

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About the area

Chestertown

Located in Chestertown, this holiday home is on the waterfront. Sumner Hall and Garfield Center for the Arts at the Prince Theater are cultural highlights, and travellers looking to shop may want to visit Chestertown Farmers Market and Queenstown Premium Outlets. Schooner Sultana and Larrabee Arts Center 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.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Sumner Hall - 21 min drive - 18.6 km
  • River Arts Chestertown - 21 min drive - 19.0 km
  • Chestertown Historic District - 21 min drive - 19.3 km
  • Historical Society of Kent County Maryland - 21 min drive - 19.3 km
  • Washington College - 22 min drive - 19.6 km

Getting around

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

Restaurants

  • ‪Doc's Riverside Grille - ‬42 min drive
  • ‪Hardee's - ‬40 min drive
  • ‪Harbor Shack - ‬40 min drive
  • ‪Ford's Seafood - ‬36 min drive
  • ‪Waterman's Crab House - ‬38 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 29 October 2026, prices found for a 1-night stay for 2 adults at Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities on 23 November 2026 start from NZ$1,950, 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, Schooner Sultana and River Arts Chestertown. Chestertown Farmers Market and Sumner Hall 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 321 out of 325 reviews
Rating 8 - Good. 4 out of 325 reviews
Rating 6 - Okay. 0 out of 325 reviews
Rating 4 - Poor. 0 out of 325 reviews
Rating 2 - Terrible. 0 out of 325 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, very clean property with wonderful view.
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was absolutely beautiful. It had three very comfortable bedrooms, which was perfect for our group of three couples. The kitchen is well stocked. The dock is perfect for fishing and crabbing. Our husbands had plenty of room to fish together. We've already booked it again for next year.
Stayed 7 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
place is clean
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is our 2nd year. Love it here. We will be back.
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was clean and right on Chester River with beautiful sunsets. The beds were comfortable. The kitchen was stocked with everything u would need. We used rhe crab pots and caught 18 crabs. We had a wonderful time at Cliffs Point Retreat. I would definitely recommend for ur next trip.
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved this house and would absolutely stay here again. It's much bigger than it looks from outside. The main area is open with great views of the water and tons of places to lounge. Of course the best feature was having the river right in the backyard.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and well accommodated. We will be back soon!
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We were very pleased with all aspects of our booking of this property. Location is secluded, on the water, with an amazing dock. Thoughtful details and curated decor show that the owners care about the property. Kitchen is well-stocked; for longer stays, there are many games, books, kayaks, bikes to enhance your time. Nature lovers will enjoy the sea birds, purple Martin birdhouse, the large willow oak in front of the house, walks on the quiet, wooded street, access to the water. Nearby Chestertown is a cute, historical town with quaint shops and bakery. There are also other towns to explore nearby. Thank you!
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
.
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay! The location is beautiful and well equipped. Warm and welcoming with beautiful views and welcoming decor. Truly a retreat.
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great!
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We love this house and have been here forMany years.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
My family and I had an awesome time we had fun in the water you had fun fishing our dogs had fun playing around overall we had a good time I had cookouts good time for all great for family
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We have enjoyed Cliff Point Retreat several times now. Come relax- all is well from A to Z. We always bring our boat to take the kids crabbing and fishing. The dock is so nice, also the huge deck with sitting and dining space, if you wish. The kitchen has everything one needs to cook BL&D!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Been going to this home for seven years with my family and it’s the perfect summer vacation for us. The property is cute and cozy with spectacular views of the Chester river. Chestertown is a short 15 minute drive from the property and we love going into town for the farmers market on Saturday and popping into Bookplate the local bookstore. Highly recommend Modern Stone age for their sourdough pizza, the white pizza is phenomenal. The water is really the highlight. You really can’t beat waking up to that view every morning. If you choose to rent here you will have an unforgettable stay!
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely love the place. We have one suggestion how about getting hot tub!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Always a beautiful stay with an endless view
Stayed 7 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely stay as always! Appreciate the accommodations- clean and comfortable.
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

As always, a wonderful stay!

Absolutely beautiful location and property!
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Golf Trip

Overall was an excellent place to stay!
Stayed 2 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful place

Very peaceful and relaxing. Will stay again
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house had everything we needed. Comfortable beds and pillows. This was our second time and we loved it.
Stayed 7 nights in Sep 2025
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