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

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Beach towels
Smart TV, fireplace, video games, DVD player
Terrace/patio
Fridge, microwave, oven, stovetop
Outdoor pool

Reviews

10 out of 10
Exceptional

Entire home

7 bedrooms7 bathroomsSleeps 28641 sq m

Popular amenities

  • Hot tub
  • Parking available
  • Washer
  • Barbecue grill
  • Pet-friendly

Explore the area

Map
Cambridge, MD
  • Harriet Tubman Museum and Educational Center
    ‪25 min drive‬
  • Choptank River Lighthouse
    ‪26 min drive‬
  • Harriet Tubman Underground Railroad National Historical Park
    ‪34 min drive‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪50 min drive‬

Room options

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

This 6,900 square foot 7 bedroom 6 - 1/2 bathroom waterfront estate home with enormous swimming pool comfortably sleeps 28 people. "Captains Quarters on the Bay" sits on 3 private acres providing the most impressive south westerly Sunset Views of the Chesapeake Bay and the Little Choptank River. This destination property offers swimming, hot tub fishing, crabbing, boating, hunting, games, game room, 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, Shuffle Board, horseshoe pit, 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 and sunset views. Two kitchens, one downstairs for poolside service and a new Gourmet Kitchen on the main floor offering a large flat top stove, triple ovens, under counter ice maker and 2 dishwashers for making great family meals. A Large Rec-room with large screen TV, games, air hockey, XBOX360 and pool table provide space for everyone.

Keywords: Chesapeake Bay Retreat, veteran owned, waterfront vacation home, Family Reunion, privacy, corporate retreats, religious group retreats and meetings, Waterfront Estate, eastern shore, special events, crabbing, fishing, private dock, family reunions, retreats, vacation, small weddings, family reunions, anniversary gatherings, Captains Quarters on the Bay.
During your stay at this holiday home, you'll be close to Spocott Windmill. Enjoy features like an outdoor pool, 1 hot tub and an arcade/games room. Free WiFi and a private pool are available in the holiday home.
  • Air-conditioned home with private pool, kitchen and washing machine
  • Free WiFi
  • Take a swim in the outdoor pool or soak in the hot tub
  • On-site recreation includes a playground
  • 6.1 miles (9.9 km) from Christ Rock Park and 6.5 miles (10.5 km) from Snows Turn Park
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 offers its guests an outdoor pool and Access to hot tub. Barbecue grills, an arcade/games room, and local meal delivery service are also featured at the family-friendly Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28.

Property manager

Frank Reagoso

Languages

English

Property amenities

Beach

  • Beach towels

Pool/Spa

  • Hot tub
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Kitchenette
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 7 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 6.5 bathrooms
  • Bathtub or shower
  • Bidet
  • Hair dryer
  • Jetted bathtub
  • Shower
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • DVD player
  • Games
  • Smart TV with cable/satellite channels
  • Video games

Outdoor areas

  • Balcony
  • Charcoal grill
  • Firepit
  • Outdoor furniture

Laundry

  • Laundromat nearby
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • Up to 23 kg per pet

Suitability/Accessibility

  • Smoke-free property
  • Note from host: Outdoors only

Services and conveniences

  • Iron/ironing board
  • Meal delivery service

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina
  • On a river
  • On the waterfront

Things to do

  • Arcade/game room
  • Billiards/pool table
  • Golf
  • Kayak
  • Water sports equipment
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Hunting nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Rafting nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Property located in a resort
  • Unit size: 6,900 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM
Contactless check-out

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 (weight limit: 50 lb per pet)
    • Service animals are exempt from fees.
  • Note from host: call owner for details

Children and extra beds

  • Children are welcome.
  • Note from host: pool, hot tub, basketball, horseshoes, gameroom +

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 45
Note from host: With advance permission in writing by Owner only
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 and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.

Property is also known as

Estate

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

Reviews

10

Exceptional

Rating 10 - Excellent. 71 out of 77 reviews
Rating 8 - Good. 5 out of 77 reviews
Rating 6 - Okay. 1 out of 77 reviews
Rating 4 - Poor. 0 out of 77 reviews
Rating 2 - Terrible. 0 out of 77 reviews

9.6/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

10/10 Excellent

Ellianna D.

Liked: Cleanliness
Unforgettable weekend at Captain's Quarters
Our stay at Captain's Quarters in Maryland was simply incredible! From the moment we walked through the door, I was struck by how spotless everything was. The views from the property were breathtaking, showcasing the beauty of the area and providing a perfect backdrop for our memorable moments. We were a large group and worried about packing everything we’d need, but to our surprise , Captain's Quarters was fully equipped! We found all the cooking and serving utensils we could ever need, and there were plenty of towels and blankets for everyone, which really eased our minds. As someone who values a safe and comfortable environment, we all felt completely at ease here. It was perfect for our family gathering; everyone got to unwind, chat, and enjoy each other's company. The highlight had to be the pool and hot tub! There was nothing better than relaxing after a long day of activities and feeling all the stress melt away. The kids had an absolute blast, and so did the adults! I can’t recommend Captain's Quarters enough for anyone looking for a spacious and accommodating place to create lasting memories with loved ones. We left with full hearts and can’t wait to plan our return! This wonderful home truly made our family time special.
Stayed 3 nights in Sep 2024

10/10 Excellent

Nicholas D.

Liked: Cleanliness
Perfect
If you have a large family this is the place to stay. The place is huge and very well equipped. The kitchen set up was the best we’ve ever had. The house and grounds were very clean and organized. The pool is nice and the dock is very convenient if you’re renting a boat or paddle board. Very highly recommended
Stayed 7 nights in Aug 2024

10/10 Excellent

Chris M.

Liked: Cleanliness
Family vacation
Great property for a family get together.
Stayed 7 nights in Jul 2024

10/10 Excellent

Bill P.

Liked: Cleanliness
Amazing Week with Family on the Waterfront
Everyone had an opportunity to do a variety of activities, outside and in, to their heart’s content! The week went by way too fast but we all left with fond memories.
Stayed 7 nights in Jul 2024

10/10 Excellent

Charles M.

Liked: Cleanliness
Lovely Week on the Chesapeake
We enjoyed the house and its amenities very much, lots of things to keep our group busy. Very nice and well equipped kitchen, as well as a lovely second floor porch overlooking the pool and water. Nice chairs on the porch, but they needed cushions to be really comfortable. Pool is very nice with plenty of seating and umbrellas.
Stayed 7 nights in Jun 2024

10/10 Excellent

Leandra K.

Liked: Cleanliness
Great Family Weekend
Spent a long weekend here with my parents, siblings and our families (including children from 6mo-5yrs). Incredibly happy with our stay--we had some fickle weather but were able to enjoy both the water and property in between the rain. The kids loved going out on the kayaks and we brought some paddleboards as well. We also enjoyed the shuffleboard, outdoor fireplace, and pool and the large flat backyard ended up being perfect for a bocce tournament with the set we brought. The house had plenty of space for everyone when the rain kept us inside. Loved having family dinners and building buzzles on the exta long dining room table. The storage bin full of games/sports equipment was great to have. Only very minor complaint is that the cornhole beanbags were a little worse for the wear and are due for a replacement. Overall very happy with our stay and highlt recommend this property.
Stayed 3 nights in May 2024

10/10 Excellent

Kaitlyn R.

Liked: Cleanliness
A beautiful place for a beautiful time
I rented the property for my 30th birthday and invited all of my friends and family. We had such a good time! The property was beautiful and the house was spacious. Everyone had a blast. There were a few minor issues, but the property manager was amazing and very responsive.
Stayed 3 nights in Mar 2024

10/10 Excellent

Deepak K.

Liked: Cleanliness
Great Escape with family & friends
Great location, grand house with all the desired amenities to make your holidays interesting and relaxing. We enjoyed working with the owner, he is prompt, emphatic and very helpful. Recommended place.
Stayed 3 nights in Dec 2023

10/10 Excellent

Angela D.

Liked: Cleanliness
Excellent family reunion location
We were a family of 14 and needed a lot of bedrooms for a family reunion vacation. The property was perfect for us. We were able to bring our boat for some much needed family fun. Everyone had a fantastic time exploring the area. Any issues we had with the property were immediately attended to by the owners. They were very quick to respond and help us out on some basic stuff. The owners have caretakers in the area and they came over if we needed them. Highly recommend this property. It was truly fun to explore the Chesapeake Bay area. Thanks for helping us create many family memories!
Stayed 7 nights in Aug 2023

10/10 Excellent

Rick and Nancy F.

Liked: Cleanliness
Family gathering
Enjoyed the variety of beds for all the kids and grandkids. Pool was great! It was fun to catch and eat crabs.
Stayed 7 nights in Jul 2023

8/10 Good

Bonnie J.

Liked: Cleanliness
Family Vacation
Great property for our family of 10 adults and 13 children ages 3-17. Enjoyed the pool, hot tub, kayaks, crabbing, we brought paddle boards and some yard games and had a great time. House had plenty of room for all of us to be comfortable and spend time together.
Stayed 7 nights in Jul 2023

10/10 Excellent

Natalie M.

Liked: Cleanliness
Wonderful Wedding Weekend
We hosted our small family only wedding at Captain’s Quarters and it was the perfect venue. The outdoor space is right on the water and beautiful. As our family is from out of town we stayed for a long weekend there was plenty of space and privacy for everyone with 5 master bedrooms and a loft for the kids. We had a great time
Stayed 4 nights in May 2023

10/10 Excellent

Abigail M.

Liked: Cleanliness
Great place for big get together
We loved this property. We used it for our family and the fact that all the bedrooms had their own private bathroom was amazing. There was also so much to do- everyone was entertained and had a blast!
Stayed 3 nights in May 2023

10/10 Excellent

Amy G., Hughesville, Pennsylvania

Liked: Cleanliness
Wonderful weekend!
We had a wonderful weekend here. The hosts were extremely responsive both before and during our stay. The property is in great shape with very comfortable furnishings.
Stayed 3 nights in May 2023

8/10 Good

Shawann K.

Liked: Cleanliness
First Cousin’s Reunion
There was plenty of room in the home. The kitchen was fully stocked. The amenities were awesome! There was plenty of yard and a dock on the water. Plenty of cookout space. I could go on. This house had everything you could imagine or need for a family reunion. We really enjoyed our stay. I would definitely rent again.
Stayed 3 nights in Mar 2023

10/10 Excellent

walter z.

Liked: Cleanliness
Peace on Earth!
This property was above and beyond the description! It was like a paradise for 3 generations. There was something to do for everyone. We love the house so much that we stayed there all day on Saturday and just enjoyed it. Normally we are out and about. The sunsets are breathtaking! The house is super clean and stocked for our needs. It is huge. We didn't even realize there is a small kitchen downstairs until we got there. We had a small bathroom issue and the property manager was over promptly to fix it. We have been doing Fall trips for over 10 years and this is one of our favorite properties! Thank you for sharing it with us! God Bless You!
Stayed 3 nights in Oct 2022

10/10 Excellent

Shira S.

Liked: Cleanliness
Great stay!
This property was perfect for my group of friends for a weekend! There were 12 of us and we all fit very comfortably with our own rooms and bathrooms. The house was clean and well equipped with everything we needed. It rained for the entire weekend which was a bit of a bummer so we weren't able to use all of the amenities but they looked like a lot of fun!
Stayed 3 nights in Sep 2022

10/10 Excellent

Amanda M.

Liked: Cleanliness
Wedding weekend that we will never forget!
Words can’t explain how amazing and perfect Captains Quarters is! We hosted our small wedding at this gorgeous location and it was everything and more than we could have ever dreamed of. The house was perfect for all of our friends and family. It was set up so thoughtfully with all ages in mind from the kids play place, baby gates, and high chairs, to the hot tub, double appliances, and game tables. The outdoor area had everything to relax and entertain. The sunsets were gorgeous overlooking the beautiful water. Frank was so accommodating and kind throughout the whole process. Overall, this property helped make the weekend unforgettable. My family and I look forward to coming back!
Stayed 3 nights in Sep 2022

10/10 Excellent

steve b.

Liked: Cleanliness
GREAT EXPERIENCE-GREAT PROPERTY
While we had a few problems early on with the air conditioning on the bottom floor- It was an electrical problem taken care of immediately- The people who did the work were outstanding, unobtrusive and knowledgeable - Sort of felt like our extended family - wanted to invite them for dinner :) WE HAD A GREAT TIME- Kids loved the water front- My middle son brought his boat down - docked it at the dock on the property. Went out two three sometimes four times a day- Can't say enough about this property and Franks response to any real or perceived problem you might have. AND AS A BONOUS- 6 crab pots on the dock when we arrived - picked up over 7 doz crabs over the week A ++++++++++++++++++++++++++ALL THE WAY. Thanks Steve Borfella
Stayed 7 nights in Aug 2022

10/10 Excellent

Nancy Anne C.

Liked: Cleanliness
Family Reunion
We booked this property, for a family reunion, while in N Carolina visiting family. This house has plenty of room for all of the families that came. We were able to go crabbing, fishing, kayaking, swimming, play board games, and cook plenty of food while we were there! We all had a great time coming together……from Ca, Fla, NY, Pa, and NC!
Stayed 7 nights in Jul 2022

10/10 Excellent

Robert and Janice H.

Liked: Cleanliness
Family Gathering
Captains Quarters is a perfect place for a large gathering. We rented the house for a week where our family that is scattered across the country came together. We live only a little over two hours away so this was convenient for those family members who could only stay a short time. There is so much to do around the property that we just stayed put the entire week.
Stayed 7 nights in Jun 2022

10/10 Excellent

ELIZABETH A.

Liked: Cleanliness
The view is amazing
We had a group of 13 adults. The house fit us well except that the single beds were too short for my grown sons. The pool was a huge hit (bring music!) and kayaks were fun (wear water shoes - the oyster shells in the water are sharp). Kitchen and dining room was well equipped for large groups.
Stayed 3 nights in Jun 2022

10/10 Excellent

Sarah W.

Liked: Cleanliness
Work Retreat
We had a group of 17 stay for an entire weekend and we were incredibly impressed by the space this stay offered. We felt as though there was plenty of room, the place was clean and the amenities were the highlight! We spent the weekend kayaking in the bay, swimming in the pool, playing basketball, shuffle board, grilling outside etc. and we could not have asked for a more versatile and welcoming space to enjoy. Some things to note is that there is a minimal WiFi connection and several people had encounters with ticks, but other than that, everything went smoothly and we would highly recommend this place to anyone looking to get away with a large group! Overall, we were incredibly happy with our stay and can't thank the owners enough for letting us enjoy the weekend on the water.
Stayed 3 nights in May 2022

8/10 Good

Patricia S.

Liked: Cleanliness
Breathtaking location and views
This house was wonderful! Beautiful waterfront and stunning sunset views on the dock. We had 22 adults in our group and had more than enough space to spend time altogether and enjoy the property. Be sure to check out the number of twin vs. queen/king beds if you have many couples in your group.
Stayed 3 nights in Apr 2022

10/10 Excellent

Jennifer G.

Liked: Cleanliness
Great multigenerational vacation
We stayed for six days and had a terrific time. Even on chilly days, we good use the heated pool and hot tub. Our dog was in heaven with the huge lawn. Sunsets are as advertised. Lots of space and an easy to use kitchen. One suggestion - bring an HDMI cord for family movie night. It was a wonderful stay!
Stayed 6 nights in Apr 2022