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

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

Reviews

10 out of 10
Exceptional

Entire home

7 bedrooms7 bathroomsSleeps 286900 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Fireplace

Explore the area

View in a map
Cambridge, MD
  • Place, Harriet Tubman Museum and Educational Center
    ‪27 min drive‬
  • Place, Choptank River Lighthouse
    ‪28 min drive‬
  • Place, Long Wharf Park
    ‪28 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪57 min drive‬

Room options

About the neighborhood

Cambridge

On river.You'll be within 6 miles (10 km) of Christ Rock Park and 9 miles (15 km) of Snows Turn Park. Also within 9 miles (15 km) are Spocott Windmill and Eastern Shore Hospital Center.
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What's nearby

  • Harriet Tubman Museum and Educational Center - 27 min drive - 11.2 miles
  • Choptank River Lighthouse - 28 min drive - 11.6 miles
  • Long Wharf Park - 28 min drive - 11.6 miles
  • Gerry Boyle Park at Great Marsh - 28 min drive - 11.0 miles
  • Dorchester County Visitors Center - 28 min drive - 11.9 miles

Getting around

  • Cambridge Station - 28 min drive
  • Easton, MD (ESN-Easton - Newnam) - 50 min drive

Restaurants

  • ‪Madison Bay - ‬31 min drive
  • ‪Woolford General Store - ‬30 min drive
  • ‪The Neck District Grill - ‬27 min drive
  • ‪Maryland Blue - ‬31 min drive
  • ‪Cambridge Country Club - ‬23 min drive

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.

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Property amenities

Beach

  • Beach towels

Pool/Spa

  • Hot tub
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total (up to 50 lbs per pet)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Upper floors accessible by stairs only
  • Smoking not allowed
  • 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 available
Minimum check-in age: 25

Check-out

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

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 lbs 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 +

Events

Events allowed: family gatherings, birthday parties, weddings
With advance permission in writing by Owner only

Smoking

Smoking is not permitted
Outdoors only

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
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 there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. 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 For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

Property is also known as

Estate

Frequently asked questions

How close is Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 to the airport?

This vacation home is 28.2 mi (50-min drive) away from the Easton, MD (ESN-Easton - Newnam) airport, the closest popular airport to the property.

Does Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28?

No, there is no casino at this vacation home.

What time is check-in at Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28?

Check-in begins at 3:00 PM.

Is there free parking at Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28?

Free parking is not available at this vacation home.

Does Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 have a pool?

This vacation home features an outdoor pool.

Does Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 have a spa?

There are no spa services available at this vacation home.

How close is Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 to downtown Cambridge?

This vacation home is 7.3 mi away from Cambridge.

Reviews

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

10

Exceptional

9.6/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities
Rating 10 - Excellent. 72 out of 78 reviews
Rating 8 - Good. 5 out of 78 reviews
Rating 6 - Okay. 1 out of 78 reviews
Rating 4 - Poor. 0 out of 78 reviews
Rating 2 - Terrible. 0 out of 78 reviews

Reviews

10/10 Excellent

Phil S.

Liked: Cleanliness
Great for 10 adults and 4 grandchildren!
Stayed 7 nights in Aug 2025

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