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Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Bedrooms 7
Half Baths1
Space 6,500 sq ft
Property type estate
Minimum Stay 3 - 7 nights


About the property

Chesapeake 3+ Acre Waterfront Estate W/pool 7 Bedrooms, 6.5 Baths, (Sleeps 28)

This 6,000 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 outward towards 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 one upstairs for the main cooks (has a 6 burner stove and three ovens upstairs for making great family meals). Inside Rec-room with games, air hockey and pool table provide space for everyone.

Keywords: Chesapeake Bay Retreat, waterfront vacation home, Family Reunion, Waterfront Estate, eastern shore, crabbing, family reunions, retreats, vacation, Captains Quarters on the Bay

More Details

Frank Reagoso
Member since: 2010
Speaks english
Response time
Within 12 hours
Response rate
Calendar last updated:
25 September, 2018

About Frank Reagoso

We are in the hospitality industry and own / operate over a dozen fine hotels in PA and MD. Brian Harlan, my son in law and I, decided to enter into the vacation home rental business because we saw a great need for an owner that understands what people need and want when traveling for vacation, reunions, retreats and meetings. We are that owner! We have been in the hospitality industry for over 35 years and have learned a lot about what people want. We provide those things because we understand the traveler. When someone asks about our properties and if we provide a particular item, the answer is almost always, 'YES'. We love what we do and are committed to exceeding our guests expectations. Just in case you are wondering about the photo, Brian is the man in the front and Frank, is the back handsome guy in the back. This photo was taken in Houma in 2015, alligator country in the bayou of Louisiana.

Frank Reagoso purchased this estate in 2003

Why Frank Reagoso chose Cambridge

"Captains Quarters on the Bay" is located in Cambridge, MD with a westerly view overlooking the Chesapeake. The home has practically everything imaginable and is located on a wonderful waterfront lot with a western view of the sunsets over the Chesapeake Bay.

What makes this estate unique

"Captains Quarters on the Bay" has so many amenities: It's a very large home with 6 king bedded rooms and a one room with bunk beds, a private lighted dock, very large pool, year round hot tub, gazebo, 2 very large outdoor grills, large kitchen and dining room, a fully equipped game room with a pool table, air hockey, large screen TV with Video Games and so much more. It also includes cleaning service at check out and complete linen rental service.


Accommodation and facilities for this holiday estate rental in Cambridge

Property Type:
  • estate
  • Guests provide their own meals
Floor Area:
  • 6500 sq ft
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 28
  • Min. age of primary renter: 25
  • Children welcome ...
  • Parties/events allowed ...
  • Pets considered ...
  • Non smoking only ...
  • No Tents or Parties are permitted except when authorized in advance by Owner. The property is for use by those staying overnight only.
Location Type:
  • Resort ...
  • Water View ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer ...
  • Heating ...
  • Internet
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Parking Off Street
  • Parking for RV/Boat/Trailer
  • Telephone ...
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • Wood Fireplace ...
  • Free Wifi
  • Catering Available
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Ice Maker
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • 6 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , bath with shower
    Bathroom 2 - toilet , bath with shower
    Bathroom 3 - toilet , bath with shower
    Bathroom 4 - toilet , shower enclosure , jacuzzi , bidet
    Bathroom 5 - toilet , bath with shower
    Bathroom 7 - toilet
    Bathroom 6 - toilet , shower enclosure , jacuzzi
  • All bathrooms are ceramic and of high quality
  • 7 Bedrooms, Sleeps 28
  • Bedroom 1 - 1 extra lg. double bed
    Bedroom 3 - 1 extra lg. double bed , 1 sofa bed/futon
    Bedroom 2 - 1 extra lg. double bed
    Bedroom 4 - 1 extra lg. double bed
    Bedroom 5 - 1 extra lg. double bed , 1 sofa bed/futon
    Bedroom 6 - 1 extra lg. double bed , 2 bunk bed
    Bedroom 7 - 4 bunk bed
  • Each Bedroom is designer appointed and has Satellite TV with the exception of any bunk bed rooms.
  • Air Hockey
  • DVD Player
  • Game Room ...
  • Games ...
  • Ping Pong Table
  • Pool Table
  • Satellite / Cable
  • Stereo ...
  • Television ...
  • Video Games ...
  • Video Library ...
  • Balcony
  • Deck / Patio
  • Gazebo
  • Kayak / Canoe ...
  • Lawn / Garden
  • Outdoor Grill ...
  • Water Sports Gear ...
  • limited accessibility ...
Pool / Spa:
  • Hot Tub ...
  • Private Pool ...
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • marina
  • museums
  • playground
  • recreation centre
  • restaurants
  • synagogues
  • winery tours
Leisure Activities:
  • antique hunting
  • bird watching
  • boating
  • eco tourism
  • horseshoes
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • hiking
  • hunting
  • jet skiing
  • kayaking
  • parasailing
  • pier fishing
  • rafting
  • sailing
  • bay fishing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
"Captains Quarters on the Bay" features: a basketball Court, lighted dock, boat ramp, Kayaks, Horseshoe pit, outdoor fireplace, gazebo, picnic tables for 28+ people, Large outdoor grills, playground with swingset


Exceptional! 5/5 -
(18 traveller reviews)

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Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
average rating of 5.0 based on 18 reviews
Jersey City

Captain's Quarters is top-notch

  • 5 of 5

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!

  • Review Submitted: 04/09/2018
  • Date of Stay: August 2018
  • Source: VRBO, from HomeAway
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0 0

Great place

  • 5 of 5

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.

  • Review Submitted: 12/02/2018
  • Date of Stay: February 2018
  • Source: HomeAway
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0 0

Wonderful Vacation! Beautiful Home!

  • 5 of 5

My family and I (10 well traveled adults) spent an amazing week at the Captain's Quarters and we could not be happier! The photos barely do this home justice! Frank and Brian were both very professional to work with the entire time. We had more than enough room for big family dinners, camp fires, etc. We caught and ate our own crabs!!! I don't think anyone left the property for 4 days, no need to! Peace and quiet and some of the most beautiful sunsets! The home is well taken care of, the pool was spotless, and the grounds very nice! The time of year that we went (September) had a few bugs but NOTHING that prevented us from enjoying this great home and the lovely outdoors!!! THANK YOU FRANK !!!

  • Review Submitted: 21/09/2016
  • Date of Stay: September 2016
  • Source: VRBO, from HomeAway
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2 0

Beautiful home for gettogether

  • 5 of 5

We rented this place for 28 people with 14 kids. The house is excellent and had plenty of room for our group. The game room, outdoor pool and kayak were really outstanding

I recommend this lakefront house for a group 20+

  • Review Submitted: 01/06/2016
  • Date of Stay: May 2016
  • Source: VRBO, from HomeAway
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0 0
Frederick, Maryland USA

Excellent Place for a Small Wedding

  • 5 of 5

My husband and I rented this home for our wedding and post-wedding brunch so that our immediate family could stay and get to know one another. The house was incredibly beautiful with plenty of space and activities to keep the kids and our adult guest entertained. Our friends helped cater the wedding and brunch so the well equipped kitchen helped out tremendously. The owner Frank was very helpful and accommodating which made more relaxed for our special day. I highly recommend this please to anyone looking to bring family together. We hope to revisit again soon!

  • Review Submitted: 26/10/2015
  • Date of Stay: September 2015
  • Source: VRBO, from HomeAway
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2 0
Herndon, Virginia

Right at Home!!

  • 5 of 5

From the first inquiry to the last, the owners and managers were quick to respond to all our questions. They truly made the Captains Quarters a welcoming place for the entire family. We were given permission to host our sons rehearsal dinner( a crab feast) for 50 there. Everyone loved sitting on all the picnic tables picking crabs!! The kitchen was well equipped, spotless and everything worked. Which is amazing given the size of the property. Would definitely recommend this to anyone looking for a true Chesapeake experience. We loved the sunsets including the Blood Moon eclipse. So many eagles and osprey to entertain us over coffee. Hope to visit again.

  • Review Submitted: 06/10/2015
  • Date of Stay: September 2015
  • Source: VRBO, from HomeAway
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1 0


Nearest Airport
82 Miles
BWI Baltimore
Nearest Barpub
5 Miles
Bistro Poplar
Nearest Golf
6 Miles
Chesapeake Hyatt Resort
Nearest Train
75 Miles
Nearest Motorway
5 Miles
Route 50
Nearest Restaurant
5 Miles
Jimmie & Sook's Raw Bar & Grill
Nearest Beach
65 Miles
Ocean City

"Captains Quarters on the Bay" is conveniently located on the Chesapeake Bay at the eastern shore of Maryland in Cambridge, MD. The location of our home is approximately 6 miles from the center of Historic Cambridge, and close to St. Michael's and Easton, Maryland. The property is great for crabbing and fishing from the lighted dock. You can also rent boats, bikes and more nearby. There's golf, tennis, and beautiful bike paths nearby. Shopping for groceries and more is located on route 50 approximately 6 miles from Captains Quarters on the Bay. his spacious 6,000 +/- square foot, 7 bedrooms, 6 ½ bath waterfront home with an oversize swimming pool, comfortably sleeps 28+ 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.

Day Tripping to Annapolis or Ocean City is approximately a 1 hour drive.


Rates & Availability

Contact Owner

Additional information about rental rates

Owner's Cancellation Policy

  • No refunds for cancellations made after payment is made

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