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Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room

Photo gallery for Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room

A large house with a swimming pool and a barn, surrounded by lush greenery and a lake.
A spacious living room with a large sofa, armchairs, and a coffee table. There is a dining area with a table and chairs, and a kitchen in the background.
An aerial view of a rural property with a large house surrounded by trees and a pond.
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island with bar stools.
A lakeside setting with three Adirondack chairs and a metal fire pit under a large tree.

Reviews

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

Highlights

  • The great outdoors

    Guests love the outdoor space here.
  • Outdoor pool

    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located

    You're never far from where you need to be with this convenient location.
4 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Private pool
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Cambridge, MD
  • Place, Christ Rock Park
    ‪6 min drive‬
  • Place, Harriet Tubman Museum and Educational Center
    ‪11 min drive‬
  • Place, Long Wharf Park
    ‪12 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪48 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

B&O Railroad Room

1 Queen Bed

Captain's Quarters

1 King Bed

Chesapeake Room

1 King Bed and 2 Single Beds

Pineapple Room

1 Queen Bed

3 bathrooms

Captains Bath

Towels provided · Toilet · Shower only

lower level bath

Towels provided · Toilet · Shower only · Hair dryer

Pineapple Bath

Towels provided · Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area

About this property

Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room

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

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House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 11:00 AM

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Children

Children allowed: ages 0–17

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Events

No events allowed

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Pets

No pets allowed

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Smoking

Smoking is not permitted

Absolutely no jumping or diving into the swimming pool or creek. No running on the pool deck or dock. No glass containers in the swimming pool area.

Life preservers must be worn by anyone under age 16 while on watercraft. All others must have life preservers with them while on watercraft.

Please be respectful of our neighbors, especially at night. Noise carries along waterways.

Important information

You need to know

Property # 954012vb
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
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

About the area

Cambridge

Located in Cambridge, this holiday home is in a rural area and on the waterfront. The area's natural beauty can be seen at Chesapeake Bay and Blackwater National Wildlife Refuge, while Harriet Tubman Museum and Educational Center and Richardson Maritime Museum are cultural highlights. Travelling with kids? Consider Dorchester Arts Center and Ruark Boatworks. Discover the area's water adventures with kayaking and power boating nearby, or enjoy the great outdoors with cycling and hiking/biking trails.
Map
Cambridge, MD

What's nearby

  • Christ Rock Park - 6 min drive - 4.5 km
  • Snows Turn Park - 6 min drive - 5.2 km
  • Harriet Tubman Museum and Educational Center - 11 min drive - 10.3 km
  • Long Wharf Park - 12 min drive - 11.0 km
  • Choptank River Lighthouse - 12 min drive - 11.0 km

Getting around

  • Cambridge Station - 14 min drive
  • Easton, MD (ESN-Easton - Newnam) - 36 min drive

Restaurants

  • ‪McDonald's - ‬11 min drive
  • ‪Chick-fil-A - ‬11 min drive
  • ‪Dunkin' - ‬11 min drive
  • ‪Thaitalian Infusion Cuisine - ‬9 min drive
  • ‪Great Wall #2 - ‬10 min drive

Frequently asked questions

Does Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room have a pool?

Yes, this property has an outdoor pool.

Is Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room pet-friendly?

No, pets are not allowed at this property.

How much is parking at Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room?

On-site parking is available at the property.

What time is check-in at Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room?

Check-in begins at 4:00 PM.

What time is check-out at Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room?

Checkout is at 11:00 AM.

Where is Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room located?

This family-friendly Cambridge holiday home is located on the waterfront, within 3 mi (5 km) of Christ Rock Park and Snows Turn Park. Richardson Maritime Museum and Dorchester Arts Center are also within 6 miles (10 km).

About the host

Hosted by Rob and Gretchen Dejter

Host profile image

Welcome to Sailor’s Retreat—your peaceful escape on Maryland’s beautiful Eastern Shore.

As we enter our ninth summer of hosting, we feel incredibly grateful to share this special property with guests. Our goal is simple: to offer a relaxing, comfortable, and memorable stay in a setting that feels both private and welcoming.

The name Sailor’s Retreat reflects our love of sailing the local waterways and everything that makes this area so special. We hope you’ll enjoy the same sense of calm, beauty, and connection to the water that brings us here time and again.

During your stay, we may be on the property in a separate loft apartment above the barn (when we’re not traveling). We are very mindful of your privacy and interaction preferences—we keep a low profile and are always available if and when you need us, but otherwise give you plenty of space to enjoy your stay uninterrupted.

To keep everything at its best, brief pool maintenance is completed in the early morning and typically takes just a few minutes.

Whether you're here to unwind, explore, or simply enjoy the quiet surroundings, we hope Sailor’s Retreat feels like your own private getaway.

We look forward to hosting you!

Why they chose this property

Sailor's Retreat is down a winding country road, and tucked away on a serene creek, but five minutes away are all of the things you need: a Walmart, cinemas, and restaurants. Be sure to check out Emily's produce stand. The baked goods and local produce are outstanding!

What makes this property unique

The ground level of our home is a single step up from the outside. There are two bedrooms and a full bath on the ground level. The most breathtaking aspect of the home is the view when you walk in the front door..... a six window panoramic view of the water greets you, and the water is so close, it seems to be a step beyond the patio. Every bedroom has a view of the water! As good as the water view is, the picturesque big, red, barn is a reminder that you are on rural farmland. The game room on the lower level of the barn is stocked with indoor and outdoor games and a beautiful oak bar.

Languages:

English

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