Entire home
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
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Reviews
9.8 out of 10, Loved by Guests
Top 10% based on
3 bedrooms2+ bathroomsSleeps 9445.9 sq m
Popular amenities
Explore the area

Drayden, MD
- Place, Dennis Point Marina14 min drive
- Place, Piney Point Beach20 min drive
- Place, Patuxent River Naval Air Station24 min drive
Rooms & beds
3 bedrooms (sleeps 9)
Bedroom 1
1 Queen Bed
Bedroom 2
2 Queen Beds
Bedroom 3
1 King Bed
2 bathrooms, 1 half bathroom
Bathroom 1
Toilet · Shower only
Bathroom 2
Toilet · Shower only
Bathroom 3
Toilet
Spaces
Deck or patio
Kitchen
Balcony
Separate dining area
Garden
About this property
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
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9.8 out of 10, Exceptional, (18 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
Events allowed: family gatherings, birthday parties, weddings
Family gatherings, birthday parties, weddings
Addi
Pets
Pets allowed: dogs and cats less than 23 kg per pet (limit 2 pets total)
Dogs and cats less than 50 lbs per pet
Pet friendl
Smoking
Smoking is not permitted
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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 50
Note from host: Family gatherings, birthday parties, weddings
Addi
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
We should mention
A car is recommended for transport to and from this property
About the area
Drayden
Located in Drayden, this holiday home is on the beach. St. Mary's River State Park and Piney Point Beach reflect the area's natural beauty and area attractions include Saint Mary's Fairground and Michael P. O'Brien Athletics and Recreation Center. Montgomery Hall Fine Arts Center and Kinsale Museum are also worth visiting.

Drayden, MD
What's nearby
- Dennis Point Marina - 14 min drive - 9.2 km
- Piney Point Beach - 20 min drive - 18.8 km
- Piney Point Lighthouse - 23 min drive - 20.2 km
- Patuxent River Naval Air Station - 24 min drive - 20.8 km
- St. Mary's College of Maryland - 26 min drive - 25.2 km
Getting around
Restaurants
- St. James Deli - 29 min drive
- Hacienda Los Guayabos - 28 min drive
- SALT Waterfront Kitchen - 40 min drive
- Green Door Tavern - 24 min drive
- Chief's Neighborhood Bar - 17 min drive
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.6/10
Cleanliness
10/10
Property conditions & facilities
10/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
Verified
16 Dec 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Dec 2025
Verified
10/10 Excellent
cindy y.
16 Sept 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
cindy y.
Stayed 4 nights in Sep 2025
Verified
10/10 Excellent
Jeramie E.
8 Sept 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jeramie E.
Stayed 6 nights in Aug 2025
Verified
10/10 Excellent
Mark A.
4 Aug 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Stay and A nice Secluded Space
Mark A.
Stayed 2 nights in Aug 2025
Verified
8/10 Good
John T.
16 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Birthday Trip
John T.
Stayed 3 nights in May 2025
Verified
10/10 Excellent
Amy H.
7 Oct 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Amy H.
Stayed 4 nights in Sep 2025
Verified
10/10 Excellent
Matthew L.
9 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Matthew L.
Stayed 3 nights in Jun 2025
Verified
10/10 Excellent
David and Ilana X.
10 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place!
David and Ilana X.
Stayed 2 nights in Jun 2025
Verified
10/10 Excellent
Lisa O.
30 Aug 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lisa O.
Stayed 7 nights in Aug 2025
Verified
10/10 Excellent
Trista P.
7 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay!
Trista P.
Stayed 5 nights in Apr 2025
Verified
10/10 Excellent
John / Mary Lou C.
22 Oct 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy




John / Mary Lou C.
Stayed 5 nights in Oct 2025
Verified
10/10 Excellent
JESSICA K.
20 Nov 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet secluded stay
JESSICA K.
Stayed 3 nights in Nov 2024
Verified
10/10 Excellent
James
18 Mar 2025
Liked: Cleanliness, property conditions & facilities, communication
James
Stayed 3 nights in Mar 2025
Verified
10/10 Excellent
Verified traveller
12 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Picturesque Paradise!
Verified traveller
Stayed 2 nights in May 2025
Verified
10/10 Excellent
Beth R.
17 June 2024
Liked: Cleanliness, check-in, communication, location
Beach house
Beth R.
Stayed 4 nights in Jun 2024
Verified
10/10 Excellent
Ryan M.
16 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful views
Ryan M.
Stayed 2 nights in Jun 2024
Verified
10/10 Excellent
Ana J.
8 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fishing trip



Ana J.
Stayed 4 nights in May 2025
Verified
10/10 Excellent
Cameron L.
23 Feb 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Spacious place in St Marys County
Cameron L.
Stayed 2 nights in Feb 2025
Verified
10/10 Excellent
Kimberlie D.
25 Sept 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy




Kimberlie D.
Stayed 5 nights in Sep 2025
Verified
10/10 Excellent
Wendy H.
18 Feb 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
What a great trip!
Wendy H.
Stayed 2 nights in Feb 2024
Verified
10/10 Excellent
George Z.
2 Aug 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family getaway
George Z.
Stayed 7 nights in Jul 2024
Verified
10/10 Excellent
jennifer l.
3 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Long weekend
jennifer l.
Stayed 3 nights in Sep 2023
Verified
10/10 Excellent
Greg S.
22 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy


Greg S.
Stayed 5 nights in Jul 2025
Verified
10/10 Excellent
Amanda N.
8 Aug 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great weekend getaway
Amanda N.
Stayed 2 nights in Jul 2023
Verified
10/10 Excellent
peggy w.
9 Sept 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
peggy w.
Stayed 4 nights in Sep 2025
About the host
Hosted by Rick Watts
My family and I moved to Southern Maryland in 2005 and have made St. Mary's our home. We love our community and are very active in giving back. I coach soccer at one of our local High Schools and serve as president for the local soccer club and my wife is an EMT with the local rescue squad. St. Mary's county is warm and welcoming with lots to explore.
Why they chose this property
Cherryfield is our dream property and has everything anyone could ever want. Whether its the private runway to fly in and out of, the private boat ramp, the 50 acres of woods to explore, large fields to run around and play, the abundant wildlife or the river to fish and crab and the 3 beaches to swim and just soak up the sun, Cherryfield truly has it all. The house has so much character and history and has tons of room to spread out and relax. The 3 screened porches provide a place for everyone to get away.
Premier Host
They consistently provide great experiences for their guests
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