Skip to main content
Entire home

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

Riverside holiday home with outdoor pool and Hot tub

Photo gallery for Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Fridge, microwave, oven, stovetop - Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 (Cambridge)
Exterior - Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 (Cambridge)
Fridge, microwave, oven, stovetop - Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 (Cambridge)
Property grounds - Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 (Cambridge)
Fridge, microwave, oven, stovetop - Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 (Cambridge)
Savor the Maritime atmosphere at Captains Quarters on the Bay, where south-westerly sunset views of Chesapeake Bay and Little Choptank River await. Enjoy swimming, fishing, or hot tub relaxation in this 7-bedroom waterfront estate with a private dock and kayaks. A game room with air hockey and pool table provides entertainment for all ages.

Reviews

10 out of 10
Exceptional

Entire home

7 bedrooms7 bathroomsSleeps 28641 sq m

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Fireplace

Add dates for prices

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.

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
  • 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
  • Up to 23 kg 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
  • 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

Similar properties

Fridge, microwave, oven, stovetop
Short drive to Downtown Cambridge | Private Dock | Guest House
  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
8.0 out of 10, Very good, 4 reviews
Short drive to Downtown Cambridge | Private Dock | Guest House

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
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total (up to 23 kg per pet)
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 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 has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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

We should mention

This property does not have any lifts

Property is also known as

Estate

About the area

Map
Cambridge, MD

What's nearby

  • Christ Rock Park - 17 min drive - 12.1 km
  • Harriet Tubman Museum and Educational Center - 22 min drive - 18.0 km
  • Choptank River Lighthouse - 23 min drive - 18.7 km
  • Long Wharf Park - 23 min drive - 18.7 km
  • Gerry Boyle Park at Great Marsh - 23 min drive - 17.6 km

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
  • ‪Church Creek Cafe - ‬22 min drive
  • ‪Maryland Blue - ‬31 min drive

Frequently asked questions

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

Yes, this property has an outdoor pool.

Is Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much is parking at Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28?

On-site parking is available at the property.

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

Check-in begins at 3:00 PM.

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

Checkout is at 10:00 AM.

Where is Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 located?

Located on the waterfront, this family-friendly holiday home is within 9 mi (15 km) of Christ Rock Park, Richardson Maritime Museum and Snows Turn Park. Spocott Windmill and Christ Episcopal Church are also within 9 miles (15 km).

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 74 out of 80 reviews
Rating 8 - Good. 5 out of 80 reviews
Rating 6 - Okay. 1 out of 80 reviews
Rating 4 - Poor. 0 out of 80 reviews
Rating 2 - Terrible. 0 out of 80 reviews

9.6/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

10/10 Excellent

Phil S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great for 10 adults and 4 grandchildren!
Stayed 7 nights in Aug 2025

10/10 Excellent

Chris M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

Great property for a family get together.
Stayed 7 nights in Jul 2024

10/10 Excellent

Bill C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for a group

Good stay overall
Stayed 3 nights in Sep 2021

10/10 Excellent

Abigail M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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

10/10 Excellent

Bill P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Don L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great

Great property, great host. Highly recommend
Stayed 4 nights in Dec 2021

10/10 Excellent

Cira Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great vacation

We had 3 families spending a week here. Very nice house with so much to do. Everyone had lots of fun. It was a great vacation during pandemic.
Stayed 7 nights in Aug 2021

10/10 Excellent

Kevin M., Austin, USA

Liked: Cleanliness, check-in, communication, location, listing accuracy

We loved it

Great house on the water...highly recommended for a large group
Stayed 3 nights in Jun 2021

10/10 Excellent

Deepak K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Rick and Nancy F.

Liked: Cleanliness, check-in, location, listing accuracy

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, check-in, communication, location, listing accuracy

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

Liz M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Family getaway

Our stay was terrific. We had 22 adults with space for all. Overall feedback from the group was all very positive. Having the pool was the best part of our stay. We enjoyed that each day and were able to play games and just overall enjoy being around each other. I would highly recommend this place for your upcoming vacation.
Stayed 7 nights in Jul 2021

10/10 Excellent

Nicholas D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Charles M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Natalie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Kaitlyn R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Jennifer G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

Jane P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for family reunion

We enjoyed this property and all of its amenities to celebrate my moms 90th birthday! A perfect place for a family getaway with enough comfortable space for everyone. We had perfect weather and the pool was awesome. We used the outdoor grills and fire place. We took our bikes and drove to Blackwater National Wildlife Refuge which is a wonderful place for a bike ride. Also visited the Harriet Tubman Visitor Center which I would recommend.
Stayed 3 nights in May 2021

8/10 Good

Shawann K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Jansey P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous Fall Retreat

The home and property were a perfect fit for our seasoned travelers. This place is well designed and set up to entertain. We sourced all of our food and supplies locally and were very happy with everything. The people and businesses of Cambridge were accommodating and pleasant to deal with. Our guests enjoyed fishing, crabbing, and kayaking as well as relaxing by the fire. The large number of beds and baths made things comfortable for all. The host was accessible, helpful and friendly. We hope to return someday..
Stayed 3 nights in Oct 2021

10/10 Excellent

Angela D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Richard G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome property

The experience was ok but Would have liked more informative from VRBO on when I would receive the welcome letter and the check in code. Only real issue was the sleep sofas which are too uncomfortable to sleep in. (No mattress). House was very comfortable and all of the appliances and facilities worked very well. Great kitchen!
Stayed 4 nights in Mar 2021

10/10 Excellent

Leandra K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

steve b.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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