Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22
“Captains Quarters on the Bay” is the perfect place for large family reunions, corporate and religious retreats during all seasons.
This spacious 6,000 +/- square foot, 7 bedrooms, 7 ½ bath waterfront home with an oversize swimming pool, comfortably sleeps 22+ people. Captain's Quarters sits on 3 private and pristine waterfront acres with a manicured lawn and provides impressive westerly views of the magnificent Chesapeake Bay sunsets. This destination property offers swimming, fishing, crabbing, hunting, dining and simply relaxing in the midst of the true maritime atmosphere on the Chesapeake Bay.
“Captains Quarters on the Bay” features: Thermostats on each floor for added comfort and has central air conditioning and heating throughout. It also features a lighted private dock, large swimming pool, basketball court, complete children’s playground, outdoor, year round hot tub, oversize outdoor gazebo, large double charcoal barbecue grill and / Fire pit which is perfect for plenty of fun for all ages during any season of the year. For your added pleasure, this home features the complimentary use of 4 kayaks and a horseshoe pit. There are plenty of picnic tables outside for entertaining. Enjoy great fishing and crabbing right from your own private dock or feel free to bring your own boat or jet skis. If you don’t have them, rentals are available with advance notice.
For those that golf, in addition to several other courses just a short drive, the world renowned Chesapeake - Hyatt Regency waterfront golf course is less than 7 miles away and is now open to the public or Take a day trip to the Harriet Tubman Museum nearby.
This home offers a large covered deck overlooking the Chesapeake Bay. “Captains Quarters on the Bay” has two kitchens; one service kitchen on the ground floor equipped with granite counters, sink, microwave oven and refrigerator / freezer for poolside service. The service kitchen is located adjacent to a comfortable sitting area with a sofa, 2 soft arm chairs and a 50 inch flat panel TV. The main kitchen on the main level on the second floor and features all granite counters, a 5 burner stove, 2 ovens and refrigerator freezer just right for making great family meals. It’s adjacent to the open Great Room / Dining Area which has a large table and plenty of seating. We have all of the china, glassware and flatware you’ll need. Small appliances such as blenders, mixers and coffee maker are provided. There are 2 complete laundry rooms, one located on the first floor and one on the second. The second floor Great Room offers an additional sitting area with a comfortable sofa, arm chairs and plenty of additional seating space. Beautiful westerly water views are experienced on all levels of the home.
The game room located on the top level is fully equipped with an oversized air hockey table, a 60 inch TV
In this 7 bedroom home there’s plenty of room for everyone! The first floor offers 3 spacious king bedrooms, 1 with queen sofa beds and seating area. The second floor offers 2 additional king bedrooms, 1 with queen sofa beds and seating. The third floor features 2 bedrooms, 1 with 4 bunk beds and another with a king bed and 1 set of bunks. This floor has twin beds located in the game room dormers.
Bring your laptop or Tablet because the home is equipped with Wi-Fi.
Don’t bother packing high chairs or cribs, they are provided! We also have 2 rollaway beds for those surprise guests.
Oh and the Sunsets!! Well they don't get any better anywhere on the Chesapeake Bay! So bring the family and friends and enjoy the Eastern Shore lifestyle!
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The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.
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
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
About the area
Cambridge
Cambridge is home to this holiday home. Spocott Windmill and Choptank River Lighthouse are local landmarks, and the area's natural beauty can be seen at Bill Burton Fishing Pier State Park and Blackwater National Wildlife Refuge. Richardson Maritime Museum and Dorchester Arts Center are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Harriet Tubman Museum and Educational Center - 22 min drive - 18.0 km
Choptank River Lighthouse - 23 min drive - 18.7 km
Long Wharf Park - 23 min drive - 18.7 km
Gerry Boyle Park at Great Marsh - 23 min drive - 17.6 km
Dorchester County Visitors Center - 23 min drive - 19.1 km
Getting around
Cambridge Station - 22 min drive
Easton, MD (ESN-Easton - Newnam) - 44 min drive
Restaurants
Madison Bay - 31 min drive
Woolford General Store - 26 min drive
Church Creek Cafe - 22 min drive
Cambridge Country Club - 21 min drive
Soft & Salty Seafood - 35 min drive
Frequently asked questions
Does Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22 have a pool?
Yes, this property has a pool.
How much does it cost to stay at Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22?
As of 9 April 2026, prices found for a 1-night stay for 2 adults at Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22 on 25 May 2026 start from NZ$3,106, 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 Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22 pet-friendly?
No, only service animals are welcome at the property.
How much is parking at Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22?
On-site parking is available at the property.
What time is check-in at Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22?
Check-in begins at 4:00 PM.
What time is check-out at Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22?
Checkout is at 10:00 AM.
Where is Captain's Quarters on the Chesapeake Bay - Pool, Hot tub, Pier and sleeps >22 located?
Situated in Cambridge, this holiday home is within 9 miles (15 km) of Christ Rock Park, Snows Turn Park and Spocott Windmill. Eastern Shore Hospital Center and Harriet Tubman Museum and Educational Center are also within 9 miles (15 km).