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

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Two level renovated stone home with all the modern amenities
salt water pool with tanning shelf and umbrella
peaceful place to read, relax, and enjoy views of the pool and barn
Welcome! Entry to open main room
Floor plan

Reviews

10 out of 10, Loved by Guests
Top 10% based on
4 bedrooms3 bathroomsSleeps 12

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Cambridge, MD
  • Place, Christ Rock Park
    ‪5 min drive‬
  • Place, Snows Turn Park
    ‪6 min drive‬
  • Place, Harriet Tubman Museum and Educational Center
    ‪11 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪38 min drive‬

Rooms & beds

4 bedrooms (sleeps 12)

B&O Railroad Room

1 Queen Bed

Captain's Quarters

1 King Bed

Chesapeake Room

1 King Bed and 2 Twin Beds

Pineapple Room

1 Queen Bed and 1 Crib

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
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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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

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

We should mention

This property does not have elevators
A car is required for transportation to and from this property

About the neighborhood

Cambridge

Located in Cambridge, this vacation home is in a rural area and on the waterfront. The area's natural beauty can be seen at Bill Burton Fishing Pier State Park and Blackwater National Wildlife Refuge, while Harriet Tubman Museum and Educational Center and Richardson Maritime Museum are cultural highlights. Traveling with kids? Consider Dorchester Arts Center and Ruark Boatworks. Be sure to check out the area's animals with activities such as game walks and birdwatching.
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Map
Cambridge, MD

What's nearby

  • Christ Rock Park - 5 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
  • Dorchester County Visitors Center - 11 min drive - 11.0 km
  • Choptank River Lighthouse - 11 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
  • ‪Starbucks - ‬11 min drive
  • ‪Great Wall #2 - ‬10 min drive
  • ‪Thaitalian Infusion Cuisine - ‬11 min drive
  • ‪The Dive Club - ‬9 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.

How much does it cost to stay at Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room?

As of Mar 26, 2026, prices found for a 1-night stay for 2 adults at Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room on Jun 19, 2026 start from $675, 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.

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?

Onsite 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?

Check-out is at 11:00 AM.

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

This family-friendly Cambridge vacation 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 mi (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 69 out of 70 reviews
Rating 8 - Good. 1 out of 70 reviews
Rating 6 - Okay. 0 out of 70 reviews
Rating 4 - Poor. 0 out of 70 reviews
Rating 2 - Terrible. 0 out of 70 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Catharine F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Rose J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Hosts thought of everything. House well appointed. Had a wonderful time.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Samie A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Edward M.

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

Vaca 25

We had a great time with our daughters and their families. What a home! Beautiful!! So well organized. All of us just loved it!!
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Kelly R.

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

Excellent getaway!

The house is beautiful and just as advertised! They think of everything you would need for a relaxing getaway!
Stayed 6 nights in Jul 2023
Verified

10/10 Excellent

Tara L.

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

Great family getaway

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.
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Susan M.

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

A week away from the hustle and bustle

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!
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Patty N.

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

Amazing property

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!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Danielle C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

David K.

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

Fantastic Property

Rob and Gretchen were amazing. This was perfect for 12 of us to celebrate my parents’ 50th anniversary. Three generations, and everybody had a great time.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Julie B.

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

Beautiful vacation house, wonderful week!

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.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

sarah w.

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

exceeded expectations

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.
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Nancy V.

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

Amazing Week!

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!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Elaine R.

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

Bay living at its best!

This property has it all! You can stay busy with swimming, boating, paddle boarding etc or pick a variety of locations to sit and enjoy a book. Great for kids of all ages. Sheets are soft, the house is immaculate and the owners have thought of everything to make your stay a memorable one. Bring your family- they will love it!
Stayed 7 nights in Jun 2019
Verified

10/10 Excellent

Barbara K.

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

Great time!

This house was perfect for our group. There was plenty of room to spread out and lots of activities for the 14 ,10 and 8 year olds. The house and ‘barn’ gamer room were well stocked and very clean. We hope to return next year!
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Jim & Katherine B.

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

A Quiet Retreat

The house is well-appointed, and there are plenty of games in the barn. The birdwatching out back is excellent, and lightning bugs dazzle at night. The beds are very comfortable. There is easy access to top-notch supermarkets and restaurants jin nearby Cambridge, and Emily’s Produce offers fresh farm produce and family fun.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Meredith H.

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

Perfect week!

It is a beautiful property, everything in the listing was just as advertised. You really did not have to bring anything other than pool towels and bug spray. Space was comfortable and well maintained. Our 10 and six year old were very happy with the pool and game room and was relaxing for all the adults as well.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Denise N.

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

Above and beyond!

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!
Stayed 5 nights in Jun 2025
Verified

10/10 Excellent

Leisa M.

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

Sailors Retreat is delightful

This property has something for everyone. It by far exceeded our expectations. The pool is perfect for families with small children. The owners had special touches that made it feel like home. Lots of space with plenty of activities. Loved the paddle boards. We spotted a bald eagle and a great heron along with some baby rays in the cove. Loved every minute of our time!
Stayed 7 nights in Jul 2023
Archival

10/10 Excellent

Valerie D.

Wow! What a place!

Perfect for our group of 3 families. Spacious, comfortable, peaceful, and well stocked. Very organized and everything was labeled. Game room was a huge hit. It was really cold outside when we were here, but the house was warm and cozy and we had plenty to do One of the nicest houses we have rented. And as nightfall struck, the geeses' reign of terror was cast over the frozen lake, and kept me up all night.)
Stayed 3 nights in Dec 2017
Verified

10/10 Excellent

Verified traveler

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

Wonderful home and location

The pool was great with the tanning ledge and umbrellas. There was no refrigerator in the game room that led to a very full fridge in the house. The dock and launch ramp were first class. Crabbing and fishing off the dock is not good but if you bring your own boat perch are a short trip away. Enjoyed the stay and the owners were very pleasant! We would absolutely stay here again.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Kristen O.

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

Great family getaway

Our family, which includes a four year old and a baby, had a great stay at sailor’s retreat. There was so much to do we didn’t need to leave the property. Our kids loved the pool - the tanning shelf was shaded and perfect for the baby to play. Tons of games (both indoors and outdoors) to keep my toddler entertained. The swing was a bonus, and boats so easy to set out for a quick paddle. The house is extremely family friendly- tons of space, clean, thoughtful touches throughout (like stools for the bathroom for our toddler). Hosts were extremely lovely, responsive, and go above and beyond— like the welcome cookies Couldn’t recommend more, we hope to be back!
Stayed 4 nights in Jun 2020
Verified

8/10 Good

Pattie M.

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

Family Vacation

The house is great, owners very responsive. There was no activity on water, which some may like but we enjoy watching boats and other water craft. Was told hot tub not available for guests but listed as amenity. The oven took a very long time to heat due to propane, there are so many signs for instruction in the house, would have expected there be instruction on this as well. Overall really enjoyed the property; pool, kayaks and game room.
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Ann C.

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

"Best Vacation Ever!"

We have rented other places on the East Coast, and have become accustomed to houses that provide renters with most everything they need. At Sailors' Retreat, however, there is so much more! Lots of games for inside and outside, a pool with toys, paddle boards, kayaks, a paddle boat, beach toys, a fire pit with plenty of wood, a wonderful barn with a pool table, a ping pong table, workout equipment and much more. Everything inside and outside is well labelled, with instructions when needed. Rob and Gretchen have thought of everything! They are so welcoming and such great hosts. All together, it was quite a wonderful week, as evidenced with the title of this review -- a direct quote from our five grandchildren!
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Octavia K.

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

Best Family Vacation Ever

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!!!!!!!
Stayed 7 nights in Jul 2024

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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