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Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992

Year Round Waterfront Estate / Family Reunions - Sleeps 28

Bedrooms 7
Separate WC's1
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 an hour
Response rate:
Calendar last updated:
3 April, 2017

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 Chesapeake Bay

"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 in Cambridge in Dorchester County

Property Type:
  • estate
  • Self-catering
Floor Area:
  • 6500 sq. ft.
House Rules:
  • Max. occupancy: 28
  • non smoking only ...
  • pets considered ...
  • Minimum Age Limit for Renters ...
  • Events Allowed
  • children welcome ...
Location Type:
  • 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 ...
  • Catering Available
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Ice Maker
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Refrigerator ...
  • Hob ...
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • 6 Bathrooms
  • 1 Separate WC
  • 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 ...
  • Pool Table
  • Satellite / Cable
  • Stereo ...
  • Television ...
  • Video Games ...
  • Video Library ...
  • Balcony
  • Terrace
  • Gazebo
  • Kayak / Canoe ...
  • Garden
  • Barbecue
  • Water Sports Gear ...
  • limited accessibility ...
Pool / Spa:
  • Hot Tub ...
  • Private Pool ...
  • churches
  • cinemas
  • festivals
  • Health/Beauty Spa
  • library
  • marina
  • museums
  • playground
  • restaurants
  • synagogues
  • winery tours
Leisure Activities:
  • antique hunting
  • bird watching
  • Boating
  • eco tourism
  • Horseshoes
  • paddle boating
  • 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
  • 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 -
(16 traveller reviews)

Year Round Waterfront Estate / Family Reunions - Sleeps 28
average rating of 5.0 based on 16 reviews

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: Sep 21, 2016
  • Date of Stay: Sep 2016
  • Source: VRBO, from HomeAway
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0 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: Jun 1, 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: Oct 26, 2015
  • Date of Stay: Sep 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: Oct 6, 2015
  • Date of Stay: Sep 2015
  • Source: VRBO, from HomeAway
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1 0

Amazing family & friends getaway!

  • 5 of 5

My wife and I rented this for a few days after our wedding as a place for family and friends to unwind after our wedding. We had such an amazing time staying at Captains Quarters. We had 12-16 guests there and still had plenty of beds available. They had everything that we could have needed, from a fully stocked kitchen with all the large pots and utensils to boil crabs to pool floaties/toys for the kids to play with. Every day was a feast of crabs which we had caught right off the dock with the supplied crabbing gear. Their are 4 kayaks, two of which are 2 seater, and plenty of life jackets(both child & adult size) allowing up to 6 of us to explore the area by kayak. The double outdoor charcoal grill was perfect for grilling up some steaks and burgers for dinner. The kids loved the game room with full size air hockey and pool table and and we took full advantage of the large lawn to play a few games of bocce and bags (which we had brought) and a few games of horse shoes in the game pit (supplied). The pool and hottub were amazing. The pool was the perfect temperature(guessing high 80's) and the hottub was a great place to hop into at the end of the day to relax. There was plenty of towels staged in each room for everyone throughout our stay as well.

We loved our time at Captains Quarters and would definitely love to go back in the future. Frank was extremely friendly and made the entire process booking through checking out an easy process. In short we had an amazing time at Captains Quarters and overall a great experience. I almost forgot to mention that the property and all its large patios face west, overlooking the water and AMAZING sunsets! I would highly recommend this property to anyone.

  • Review Submitted: Sep 28, 2015
  • Date of Stay: Sep 2015
  • Source: VRBO, from HomeAway
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1 0
Mount Holly NJ USA

The most charming vacation home

  • 5 of 5

What a wonderful place to have a vacation...so much to do you never have to leave! Outside activities include the pool, hot tub, kayaking,crabbing, basketball, badminton, horseshoes, playground. Inside you will find air hockey, pool, Xbox, televisions and DVDs, games. The eating area was wonderful...what a table! Sleeping arrangements were great...10 adults and 13 kids. The owner was friendly, and very helpful. Even returned a camera we forgot! Could not find a nicer spot...beautiful sunrise...beautiful sunsets! Hope we can come again!

  • Review Submitted: Jul 20, 2015
  • Date of Stay: Jul 2015
  • Source: VRBO, from HomeAway
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Kool Ice & Seafood Co
"Great Fresh Seafood & Steamed Crabs"
High Spot Gastropub
"Great food and pleasant atmosphere."
Bistro Poplar
"Very good food and nice people."
Hyatt Regcy Chesapeake Bay Golf
"Great Golf and Public Course"
Harriet Tubman Underground Railroad State Park and Visitor Center
"A Very Important Landmark which will be a "Must See" for all children."
Portside Restaurant
"Not fancy but Great Crab cakes overlooking the water in Cambridge."
Nearest Airport
82 Miles
BWI Baltimore
Nearest Barpub
5 Miles
Nearest Golf
6 Miles
Nearest Motorway
5 Miles
Route 50
Nearest Restaurant
5 Miles
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.


Prices & Availability

Prices for this holiday estate in Cambridge, Maryland

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
7 Apr 2017 - 29 Apr 2017
3 night minimum stay
for 3 nights
30 Apr 2017 - 25 May 2017
3 night minimum stay
for 3 nights
Memorial Day 2017
26 May 2017 - 28 May 2017
3 night minimum stay
for 3 nights
Post Memorial Day
29 May 2017 - 2 Jun 2017
3 night minimum stay
for 3 nights
Early Summer
3 Jun 2017 - 16 Jun 2017
7 night minimum stay
for 7 nights
Summer 2017
17 Jun 2017 - 25 Aug 2017
7 night minimum stay
for 7 nights
Late Summer 2017
26 Aug 2017 - 31 Aug 2017
3 night minimum stay
for 3 nights
Labor Day
1 Sep 2017 - 3 Sep 2017
3 night minimum stay
for 3 nights
4 Sep 2017 - 4 Oct 2017
3 night minimum stay
for 3 nights
5 Oct 2017 - 9 Oct 2017
4 night minimum stay
for 4 nights
Late Fall
10 Oct 2017 - 18 Nov 2017
3 night minimum stay
for 3 nights
19 Nov 2017 - 25 Nov 2017
4 night minimum stay
for 4 nights
26 Nov 2017 - 21 Dec 2017
3 night minimum stay
for 3 nights
22 Dec 2017 - 28 Dec 2017
3 night minimum stay
for 3 nights
My Standard Rate
3 night minimum stay
for 3 nights

Additional pricing information

Refundable Damage Deposit £386.51
Tax Rate 11.0%

Owner's Cancellation Policy

  • Cancelled bookings will not receive a refund.

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