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

Cambridge, Maryland
$0 avg/night Minimum Stay 5 Nights
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 5 nights

Min Stay

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 ofeveryday 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

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Recycling Uses Some LED Lighting
  • KITCHEN

    Coffee Grinder Cookware/dishes/utensils Dishwasher Kitchen Island Microwave Oven Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Firepit Outdoor Furniture Patio
  • POOL/SPA

    Fence Around The Pool Outdoor Pool Private Pool
  • BATHROOMS

    3 Bathrooms Bathtub Or Shower Hair Dryer Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Cycling Nearby Fishing Nearby Hiking Nearby Hiking/biking Trails Nearby Kayak On Site Marina Nearby Power Boating Nearby Sailing Nearby Water Sports Equipment Winery Tours Nearby
  • ENTERTAINMENT

    Arcade/game Room Books Games Pool Or Billiards Table Table Tennis Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Games Children's Toys Highchair Playground
  • LOCATION HIGHLIGHTS

    In A Rural Location Near A Hospital Near The Sea On The River On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Upper Floors Accessible By Stairs Only Wheelchair Accessible

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • Danielle C.

    Submitted Sep 2, 2025

    Stayed Aug 23, 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!

  • Catharine F.

    Submitted Aug 10, 2025

    Stayed Aug 3, 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.

  • Rose J.

    Submitted Aug 7, 2025

    Stayed Jul 12, 2025

    Hosts thought of everything. House well appointed. Had a wonderful time.

  • Lisa W.

    Submitted Jul 26, 2025

    Stayed Jul 19, 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.

  • Samie A.

    Submitted Jul 14, 2025

    Stayed Jun 28, 2025

    The home easily accommodated our combined family of 8. Everything we needed in the kitchen was available. We all enjoyed the pool and water toys daily. Communication with the owners was easy.

  • Susan M.

    Submitted Jul 12, 2025

    Stayed Jul 5, 2025

    This house was just what we needed to get away. The check-in process was super easy. Rob and Gretchen were very quick to responding to any questions we had. The house was beautiful. Our adult kids loved going out in the kayaks and paddleboards. We enjoyed fishing off the dock. The pool was a great way to escape the July heat. Their suggestions to go to Scottish Highland Creamery, Emily's Produce and the Suicide Bridge Restaurant were on point. We would definitely stay here again!

  • Denise N.

    Submitted Jul 2, 2025

    Stayed Jun 16, 2025

    This was the perfect property for a vacation with our adult children and grandchildren! All of the activities were thoroughly enjoyed- from the kayaks, fire pit and sand pit to the pool and game center (an especially big hit with the grandchildren). Such a peaceful location on the water! The hosts were exceptionally responsive! The house was very clean and very well stocked- everything you need is provided. As the first rental of the season, we encountered two minor issues that needed addressed. The hosts went far above and beyond in addressing them! We couldn't have been more impressed with their responsiveness! Overall, a perfect location with exceptional hosts! We look forward to a return!

  • Edward M.

    Submitted Jun 28, 2025

    Stayed Jun 21, 2025

    We had a great time with our daughters and their families. What a home! Beautiful!! So well organized. All of us just loved it!!

  • Octavia K.

    Submitted Aug 5, 2024

    Stayed Jul 6, 2024

    The photos of this property do not tell the whole story. This home is incredible!!!! When we arrived, the house was clean, clearly labeled, well stocked, and has super responsive owners. The property has everything!!! Luxurious and comfortable furnishings, beautiful touches throughout, a dock for fishing and watching sunsets, striking wildlife, a perfect pool setup and a terrific game room. We had kids aged 18 to 3, and everyone had a blast!!!!! This place is a hit with young people and those who are a bit more mature. This vacation was the best family vacation I’ve ever had!!!! Some highlights: painting rocks for the garden (supplies are provided) kayaks and paddle boards, a bald eagle is resident nearby, the enclosed sun porch was perfect for watching a storm roll in, and we roasted marshmallows over the fire pit. I’m so happy we decided to stay here. Absolutely gorgeous!!!!!!!

  • Tara L.

    Submitted Aug 4, 2024

    Stayed Jul 27, 2024

    Our family enjoyed our stay here. The owners were amazing and the property and home were beautiful. There was something for everyone to do. The screened in porch was a huge bonus too. I highly recommend booking this house for your next vacation. Absolutely great week.

  • Nancy V.

    Submitted Jul 27, 2024

    Stayed Jul 20, 2024

    From start to finish, this vacation was wonderful. Gretchen and Rob thought of everything when renting out their home. From games, pool, kayaking, paddle board and fishing, the week went by quickly. Highly recommend!

  • sarah w.

    Submitted Jul 20, 2024

    Stayed Jul 13, 2024

    great hosts. house has everything u need and more. private secluded location. perfect place for alone time. or family time. would return again for sure.

  • Julie B.

    Submitted Jul 15, 2024

    Stayed Jun 22, 2024

    My family of 5 and a grandparent had a wonderful week at this property. The hosts are very responsive to any issues while maintaining privacy. The house is large, spacious, comfortable, and decorated very tastefully. The pool is an amazing amenity as is the waterfront location and kayaks. We enjoyed exploring Cambridge during our stay too. I can’t say enough good things about our week away and would definitely book again.

  • Patty N.

    Submitted Jun 30, 2024

    Stayed Jun 15, 2024

    The property was amazing...literally had every detail and item you could ask for. We really enjoyed relaxing and playing equally. Highly suggest this property for all!

Your dates are Available!

Total

Includes taxes and fees