House in Maryland
10 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Waterfront Retreat on 4 Private Acres | Pool, Dock, Kayaks & Game Barn
Welcome to your private Eastern Shore escape—where peaceful waterfront views, wide-open space, and thoughtful luxury come together for an unforgettable stay.
For nearly a decade, we’ve welcomed guests to this special property, and once you arrive, you’ll understand why so many return year after year. As you wind down the quarter-mile driveway past a 200+ year-old sycamore, the stress of everyday life begins to fade. When the red barn and swaying willow trees come into view—you’ve arrived.
The Home
Step inside our beautifully restored stone house and take in sweeping views of Fishing Creek through a stunning wall of floor-to-ceiling windows.
The open-concept great room is designed for connection and comfort, featuring:
A fully equipped modern kitchen
Oversized dining table + custom island seating
Plush seating for your entire group
Easy access to the screened-in porch—perfect for sunset breezes
Sleeping Arrangements (Sleeps Large Groups Comfortably)
Main Level:
B&O Railroad Room: Queen bed
Chesapeake Room: King bed + twin trundle (2 beds)
Full bathroom
Upper Level (2 Private Suites):
Captain’s Quarters: King bed, ensuite bath, walk-in closet
Pineapple Room: Queen bed, ensuite bath, walk-in closet
Each suite includes a rollaway twin for added flexibility
Perfect for families, multi-generational groups, or friends traveling together.
Outdoor Living & Waterfront Fun
This is where the property truly shines:
Private dock for crabbing, fishing, or relaxing by the water
Kayaks & paddleboards available for guest use
Gentle boat ramp for your own watercraft
4 scenic acres to explore, play, and unwind
Pool + Barn
Saltwater pool with tanning ledge + umbrella seating
Expansive barn game room with:
Pool table
Ping pong
Air hockey
Darts
Plus a large open field for cornhole, croquet, or your favorite outdoor games.
Evenings to Remember
Gas grill for easy cookouts
Fire pit with provided firewood
Perfect setting for s’mores, stargazing, and storytelling
Explore the Area
Located near charming Cambridge, you’re close to some of the Eastern Shore’s best experiences:
Waterfront dining with fresh local seafood
Breweries and shops along Race Street
Nature and wildlife at Blackwater National Wildlife Refuge
History at the Harriet Tubman Underground Railroad Visitor Center
Resort amenities and golf at Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina
Your Stay
You’ll have full, private access to the property during your stay. Occasionally, we may be in the barn loft apartment when not traveling—but we fully respect your privacy. If you’d like local tips or a friendly chat, we’re always happy to connect.
Why Guests Love It
✔ Waterfront + private dock
✔ Pool + game barn = fun for all ages
✔ Peaceful, secluded setting (yet close to town)
✔ Ideal for families & group getaways
✔ Thoughtfully designed for relaxation and connection
Welcome to your private Eastern Shore escape—where peaceful waterfront views, wide-open space, and thoughtful luxury come together for an unforgettable stay.
For nearly a decade, we’ve welcomed guests to this special property, and once you arrive, you’ll understand why so many return year after year. As you wind down the quarter-mile driveway past a 200+ year-old sycamore, the stress of everyday life begins to fade. When the red barn and swaying willow trees come into view—you’ve arrived.
The Home
Step inside our beautifully restored stone house and take in sweeping views of Fishing Creek through a stunning wall of floor-to-ceiling windows.
The open-concept great room is designed for connection and comfort, featuring:
A fully equipped modern kitchen
Oversized dining table + custom island seating
Plush seating for your entire group
Easy access to the screened-in porch—perfect for sunset breezes
Sleeping Arrangements (Sleeps Large Groups Comfortably)
Main Level:
B&O Railroad Room: Queen bed
Chesapeake Room: King bed + twin trundle (2 beds)
Full bathroom
Upper Level (2 Private Suites):
Captain’s Quarters: King bed, ensuite bath, walk-in closet
Pineapple Room: Queen bed, ensuite bath, walk-in closet
Each suite includes a rollaway twin for added flexibility
Perfect for families, multi-generational groups, or friends traveling together.
Outdoor Living & Waterfront Fun
This is where the property truly shines:
Private dock for crabbing, fishing, or relaxing by the water
Kayaks & paddleboards available for guest use
Gentle boat ramp for your own watercraft
4 scenic acres to explore, play, and unwind
Pool + Barn
Saltwater pool with tanning ledge + umbrella seating
Expansive barn game room with:
Pool table
Ping pong
Air hockey
Darts
Plus a large open field for cornhole, croquet, or your favorite outdoor games.
Evenings to Remember
Gas grill for easy cookouts
Fire pit with provided firewood
Perfect setting for s’mores, stargazing, and storytelling
Explore the Area
Located near charming Cambridge, you’re close to some of the Eastern Shore’s best experiences:
Waterfront dining with fresh local seafood
Breweries and shops along Race Street
Nature and wildlife at Blackwater National Wildlife Refuge
History at the Harriet Tubman Underground Railroad Visitor Center
Resort amenities and golf at Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina
Your Stay
You’ll have full, private access to the property during your stay. Occasionally, we may be in the barn loft apartment when not traveling—but we fully respect your privacy. If you’d like local tips or a friendly chat, we’re always happy to connect.
Why Guests Love It
✔ Waterfront + private dock
✔ Pool + game barn = fun for all ages
✔ Peaceful, secluded setting (yet close to town)
✔ Ideal for families & group getaways
✔ Thoughtfully designed for relaxation and connection
Amenities at Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room
Non-smoking
No pets allowed
Family friendly
Map of Maryland
Ratings and reviews
10 / 10Outstanding·Sep 2025
This property is a dream. It was immaculant, had every little ammenity that you could think of to make your stay as comfortable as possible, and had so many fun activities. We were never bored! The pool was beautiful, my bedroom suite was so perfect that I didnt want to leave it. I spent so much time in the cute window seat overlooking the river and dock reading one of the books that were on the very full bookshelf. There were chairs, swings and unique seating everywhere to enjoy every part of the beautiful property! The owners were so sweet and easy to get in contact with. I would definitely recommend to anyone, especially larger families. We would love to stay again one day!
10 / 10Outstanding·Aug 2025
Beautiful location, well appointed inside (the hosts thought of everything) and so many options of fun outside with swing, hammock, fire pit, pool and dock.
10 / 10Outstanding·Aug 2025
Hosts thought of everything. House well appointed. Had a wonderful time.
10 / 10Outstanding·Jul 2025
This property is perfect for large families with children of all ages. First, the house is spacious, well appointed for cooking and having together time. We took turns preparing nearly all of our meals for the 10 of us during our week long stay and the kitchen has all of the necessities and so much more. The beds and linens were comfortable for resting well each night after our very busy days. The dock was in constant use by the fishermen in our group and we were even successful with the crab traps! The game room was a favorite of my grandsons who learned how to play pool and perfected their ping pong and cornhole skills. But the favorite spot by far was the beautiful salt water pool and pool patio where we spent considerable time every day. Sailors Retreat is a destination stay, you really wouldnt have to leave the beautifully landscaped property to enjoy a week in the eastern shore. We did however make several outings during our stay, Harriet Tubman historical sites, the nearby wildlife refuge, and a trip to Asseteague to play on the beach and see the wild ponies was a highlight. Cambridge has many cute shops and restaurants. Its also worth the drive to Oxford to get an ice cream at the Scottish Highland. Both the kiddos and the adults had fun painting a special rock so that a piece of their creativity is left behind in exchange for the great memories we have brought home with us. Thank you so much Rob and Gretchen for providing such a perfect place for family time.
$$$$
Top rated by guests
10Outstanding
(69 Ratings)
"This property is a dream. It was immaculant, had every little ammenity that you could think of to make your stay as comfortable as possible, and had so many fun activities. We were never bored! The..."
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