Last Updated: November 04, 2026
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Chesapeake 3+ Acre Waterfront Estate W/pool 7 Bedrooms, 6.5 Baths, (Sleeps 28)
This 6,900 square foot 7 bed 6 bath waterfront home with enormous swimming pool comfortably sleeps 27 people comfortably. "Captains Quarters on the Bay" sits on 3 private acres providing impressive south westerly views of the Little Choptank River and the Chesapeake Bay. This destination property offers swimming, fishing, crabbing, boating, hunting, dining and relaxing, in the midst of true Maritime atmosphere of the Chesapeake bay.
A private dock with kayaks, fenced swimming pool, year round hot tub, basketball court, splinter free playground, large manicured waterfront lawn with a horse shoe pit, large gazebo, double built in charcoal grills and outdoor fire pit make for great outdoor activities for all ages. The world renown Hyatt Regency waterfront golf course is less than 7 miles away and is open to the public.
The home offers deluxe living complete with designer furnishings, and a large wrap around covered porch with awesome water views. Two kitchens, one downstairs for poolside service and a new "2019" Gourmet Kitchen upstairs for the main cooking (which offers a large stove, triple ovens, under counter ice maker and 2 dishwashers for making great family meals). Large Rec-room with large screen TV, games, air hockey, XBOX360 and pool table provide space for everyone.
Keywords: Chesapeake Bay Retreat, waterfront vacation home, Family Reunion, corporate retreats, religious group retreats and meetings, Waterfront Estate, eastern shore, crabbing, family reunions, retreats, vacation, Captains Quarters on the Bay
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Parties/events allowed
With advance permission in writing by Owner only
No smoking
Outdoors only
Pets allowed
call owner for details
Children allowed
pool, hot tub, basketball, horseshoes, gameroom +
Minimum age of primary renter:25
Max guests:28
No Tents or Parties are permitted except when authorized in advance by Owner. The property is for use by those staying overnight only.
Cancellation Policy
Canceled bookings will not receive a refund
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| Bedroom 1 |
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| Bedroom 2 |
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| Bedroom 3 |
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| Bedroom 4 |
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| Bedroom 5 |
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| Bedroom 6 |
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| Bedroom 7 |
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| Child Friendly |
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| Dining Room |
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| Fireplace |
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| General |
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| Home Office |
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| Hot Tub and Sauna |
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| Kitchen |
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| Layout and Decor |
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| Outside Living |
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| Parking |
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| Swimming Pool |
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| Nearby Amusement Parks |
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Peak Season Includes Weekends, National Holidays and Other Festivals |
John M.
This house had everything you could need for a big group. Plenty of space for 25 people and a a breathtaking view of the bay.
Cody R.Jersey City
My family and friends could not be happier with our experience staying at the Captain's Quarters on the Chesapeake Bay. It had everything you could ask for. Attentive management, extreme cleanliness, ample space and close enough to Cambridge to get any items you may have forgot. The yard was well kept, the pool and hot tub were perfect temp and AC in house was lovely. Wifi was also great and the experience fishing and crabbing was a total treat. Overall, it was an A+ experience that we will certainly be coming back for!
Amy C.
Everything was perfect! The property had everything we needed and more. We had 8 children with us and they were entertained from the time we arrived until the time we departed. We can’t wait to do this again!
Jennifer M.Berkeley Heights NJ
We had a wonderful stay at this property - perfect for our family reunion. The large property was great for playing yard games, the pool was clean and well maintained. Several in our group used the kayaks - the inlet was large enough for a good paddle but also quite calm, so the novices felt very comfortable. Well-equipped kitchen - could maybe use a bit more couch-type seating in the living room areas, but you want to spend most of your time outside anyway, so not a big deal at all. Would definitely recommend and come back.
S B.
The home comprised many interesting spaces. It was well equipped with toys and first-rate kitchen equipment. We had a wonderful time.
Ed P.
Franks team was great to deal with. The property was very clean, plenty of activities to do in the area. Overall, it was a great house to have a company meeting
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