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Waterfront Family Retreat with Pool on 7+ acres!

Photo gallery for Waterfront Family Retreat with Pool on 7+ acres!

A wooden pier leading to a two-story house with a porch, surrounded by trees and a body of water.
A modern kitchen with white cabinets, a black countertop, and wooden flooring. There are three bar stools and a window with a view of the outdoors.
A balcony with a view of a lake, a dock, and a white house with blue shutters.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden island with bar stools.
A rectangular swimming pool with a wooden deck and lounge chairs.

Reviews

10 out of 10
Exceptional

Highlights

  • Cook, dine, and unwind
    Top-rated for its fully equipped kitchen, perfect for every meal.
  • Ping pong on-site
    A rare find — challenge friends and family to endless matches.

Popular amenities

  • Balcony
  • Private pool
  • Toys
  • Barbecue
  • Air-conditioning
  • Garage parking available

Explore the area

View map
Woolford, MD
  • Place, Blackwater National Wildlife Refuge
    ‪6 min drive‬
  • Place, Harriet Tubman Underground Railroad National Historical Park
    ‪16 min drive‬
  • Place, Northern Chesapeake Bay
    ‪19 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪57 min drive‬

Rooms & beds

10 bedrooms (sleeps 24)

Bedroom 1

2 Single Beds

Bedroom 2

2 Single Beds

Bedroom 3

1 King Bed

Bedroom 4

2 Single Beds

Bedroom 5

1 Queen Bed

Bedroom 6

2 Single Beds

Bedroom 7

2 Single Beds and 1 Queen Bed

Bedroom 8

2 Single Beds

Bedroom 9

1 Queen Bed

Bedroom 10

4 Single Bunk Beds

5 bathrooms, 1 half bathroom

Bath 1

Toilet · Shower only

Bath 2

Bathtub or shower · Toilet

Bath 3

Bathtub or shower · Toilet

Bath 4

Bathtub or shower · Toilet

Bathroom 5

Bathtub or shower · Toilet

Bathroom 6

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area

Add dates for prices

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10.0 out of 10, Exceptional, (9 reviews)
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About the area

Woolford

Located in Woolford, this holiday home is in a rural area and on the waterfront. Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center are cultural highlights, and some of the area's landmarks include Choptank River Lighthouse and Spocott Windmill. Travelling with kids? Consider Richardson Maritime Museum and Dorchester Arts Center. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking/biking trails and hunting.
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Map
Woolford, MD

What's nearby

  • Blackwater National Wildlife Refuge - 6 min drive - 5.5 km
  • Harriet Tubman State Park Visitors Center - 15 min drive - 16.7 km
  • Harriet Tubman Underground Railroad National Historical Park - 16 min drive - 17.4 km
  • Northern Chesapeake Bay - 19 min drive - 20.0 km
  • Choptank River Lighthouse - 21 min drive - 22.6 km

Getting around

  • Cambridge Station - 23 min drive
  • Easton, MD (ESN-Easton - Newnam) - 45 min drive

Restaurants

  • ‪Madison Bay - ‬7 min drive
  • ‪The Neck District Grill - ‬35 min drive
  • ‪Hudson Manor - ‬34 min drive
  • ‪Soft & Salty Seafood - ‬44 min drive
  • ‪5712 Speakeasy - ‬41 min drive

Frequently asked questions

Does Waterfront Family Retreat with Pool on 7+ acres! have a pool?

Yes, this property has an outdoor pool.

Is Waterfront Family Retreat with Pool on 7+ acres! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Waterfront Family Retreat with Pool on 7+ acres!?

On-site parking is available at the property.

What time is check-in at Waterfront Family Retreat with Pool on 7+ acres!?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront Family Retreat with Pool on 7+ acres!?

Checkout is at 10:00 AM.

Where is Waterfront Family Retreat with Pool on 7+ acres! located?

This family-friendly Woolford holiday home is located on the waterfront, 3.1 mi (5 km) from Blackwater National Wildlife Refuge, and within 9 mi (15 km) of Christ Rock Park and Harriet Tubman Underground Railroad National Historical Park. Richardson Maritime Museum and Dorchester Arts Center are also within 12 miles (20 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 66 out of 67 reviews
Rating 8 - Good. 1 out of 67 reviews
Rating 6 - Okay. 0 out of 67 reviews
Rating 4 - Poor. 0 out of 67 reviews
Rating 2 - Terrible. 0 out of 67 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Third year for our large family to gather at this amazing place. Outdoor activities are our thing and there is a lot to keep us busy. Great hosts. Wonderful place.
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was above our expectations. Very well stocked, pool was fantastic and having our own dock for our pontoon rental and fishing and crabbing. Our family reunion ranged from crib sleepers to our 70 year old matriarch, me...The carriage house was perfect for the 2 younger families and the main house for everyone for family dinners. We sure hope to be back someday. Thank you Glen and Cheryl.
Stayed 7 nights in Aug 2026
Response from VrboOwner on 24 Aug 2026
So glad your family was able to get together and Cherry Point worked well for all. You're always welcome back. Looking forward to hosting you again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We keep renting this property every year for a reason (actually a bunch of reasons). We’re a multi-generational family, ranging in ages from 1-76 (this year). There’s something for everyone. Boating / crabbing / fishing, swimming, tennis / pickleball, basketball, ping pong, canoeing, puzzling, reading on the new deck in the new glider rockers, and more! Highly recommended!!!Additionally, the hosts are super friendly and respond very quickly!
Stayed 7 nights in Jul 2026
Response from VrboOwner on 12 July 2026
We are so glad your family continues to enjoy the property. You're welcome back any time.
Verified review

10/10 Excellent

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

Wonderful location!

Such a fun place to stay! Never without something fun to do or if you want, a wonderful relaxation place!!
Stayed 4 nights in Sep 2021
Response from VrboOwner on 29 Sept 2021
So glad you enjoyed your getaway. You're welcomed back any time.
Verified review

10/10 Excellent

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

Family Vacation

Wonderful place for a multigenerational family vacation. Enjoyed the pool, pickleball and lots of crabs.
Stayed 7 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay for a large group of friends with kids! Plenty to do, beautiful property! Had everything you could need to enjoy fishing and crabbing off the dock and a very well stocked kitchen! We are already talking about coming back! Also loved how the doors locked with small children!
Stayed 5 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property. Salt water pool was amazing. Incredible views. Very well equipped kitchen. Owners were responsive and helpful!
Stayed 6 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nicely appointed home. Beautiful location. Family enjoyed the canoes, kayaks, fishing and crabbing from the nice dock. We even used the tennis court for pickle ball. Property is absolutely beautiful and peaceful. We'll be coming back!
Stayed 7 nights in Aug 2025
Response from VrboOwner on 21 Aug 2025
So glad your family enjoyed CP. Looking forward to hosting you again.
Verified review

10/10 Excellent

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

Family getaway

Our big family spent our annual vacation at Kathleen and Allen’s beautiful home. We had so much fun crabbing and fishing on the dock, singing and dancing around the campfire, swimming in the pool, playing badminton and wiffle ball
Stayed 5 nights in Aug 2024
Verified review

10/10 Excellent

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

Great property on bay!

Terrific
Stayed 7 nights in Jun 2023
Verified review

10/10 Excellent

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

WE LOVE IT

THIS WAS OUR SECOND TRIP TO CHERRY POINT. IT IS A BEAUTIFUL, WELL MAINTAINED PROPERTY IN A GREAT LOCATION.
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

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

GREAT place for large family

We loved having many kayaks and canoes ready to use. Wonderful swimming pool with lots of toys. So much to do inside and outside. It was great all around for all ages. Everyone felt this was a favorite place to gather.
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

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

Great vaca home for a large gathering

The house was wonderful for a large group. Owner was extremely good with communication and quick to respond and fix when one thing went wrong. Would absolutely rent from them again. Great setting and having the pool and pickleball / tennis court was a fantastic added feature that we used.
Stayed 4 nights in May 2024
Verified review

10/10 Excellent

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

What a great family vacation!

We had a group of 17 for our family vacation and we truly enjoyed every aspect of our stay! The beautiful location, the house, pool, the kayaks and canoes, yard area! It was fantastic! The house and cottage supplied ALL the space we needed for 5 family units. The only bummer was jellyfish in the bay!
Stayed 7 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house. Fantastic setting for playing outside. Lots of sports equipment for all ages. And the swimming pool! We enjoyed the pool and deck for hours everyday. The house and accommodated our large and active family. Unanimous vote to return next year.
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The pictures do not do the place justice! From the beginning the host was more than welcoming with lots of helpful information. We experienced Hurricane weather / tides and he was communicative through the entire process! Our whole group could not of loved the place more - between the awesome pool, pickleball court and overall house layout. The kitchen was well stocked whihc made cooking for a big group helpful. We look forward to staying again!
Stayed 5 nights in Aug 2025
Verified review

10/10 Excellent

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

We keep going back!

We've stayed here for our big family vacation (3 generations) for several years. There's so much to do without leaving the property. The property is very clean, and the owners make updates / upgrades every year. The owners are very friendly and responsive and always check in with us to see how we're doing. I can't say enough nice things about the property and the owners.
Stayed 7 nights in Jul 2024
Response from VrboOwner on 16 July 2024
Thanks Mary, Always great to hear that your family enjoyed Cherry Point again. Look forward to hosting you again next yr.
Verified review

10/10 Excellent

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

Loved it!

There's something for everyone at Cherry Point - pool, boat/fishing dock, tennis, basketball, volleyball, big lounge areas (including a screened-in porch). The house and the grounds are well kept, the kitchen is well stocked, and the owners are great at keeping in touch. This is our third time staying here, and we will be going again.
Stayed 7 nights in Jul 2022
Response from VrboOwner on 3 Aug 2022
Thanks Mary. Looking forward to hosting you again doon.
Verified review

10/10 Excellent

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

July 2024 stay

The property was very nice and as advertised. The only negative is location. It is pretty remote and not much to do within 30 minutes driving time.
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

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

Wonderful Week!

We had a fantastic week with our children and grandchildren. This property offers something for everyone, all ages. Volleyball was a nightly event and the pool was always being used in the 90 degree weather. The property has everything you need from the kitchen to outdoor games....very highly recommended.
Stayed 6 nights in Jun 2024
Verified review

10/10 Excellent

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

Something for Everyone

We’ve stayed here a number of times, and it’s always been enjoyable. From taking sunrise pics to boating, crabbing, and fishing, to cannonballs in the pool, to hoops on the tennis court (and maybe a little tennis), to fun family dinners, to painting parties, there’s always something to do. The place is neat and tidy, with lots of amenities. The owners are super nice, informative, and very responsive.
Stayed 7 nights in Jul 2023
Response from VrboOwner on 17 July 2023
Thanks Mary. Always great having you all stay with us. You're always welcomed.
Verified review

10/10 Excellent

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

August 2023 stay

Excellent house & pool. Family had an outstanding stay. We rented a boat part of the week, tubing, fishing, and general water fun. Kitchen was well laid out, allowing us to cook and serve family of 21. Equipment included canoes, paddle boards, ping pong, horseshoes and a tennis / paddle ball court. A first class experience.
Stayed 7 nights in Aug 2023
Verified review

10/10 Excellent

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

Family Reunion

This property offered many activities and space for our group of 23 family members! We explored the creek while canoeing, played tennis on the courts and were able to come together during meals and game nights. Everyone slept well in comfy beds and appreciated the hot showers after a long day. Central to the historical locations and an hour drive to beaches, the location works! Thanks for a great time, Allen!
Stayed 8 nights in Jun 2023
Verified review

10/10 Excellent

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

Family reconnect

We gathered as an extended family for a wonderful week at this beautiful property. The house is just perfect for a large group. We could all eat together and there was plenty for us to do- pool, pickle ball, tennis, paddle boards, kayaks, fishing, crabbing. One of the highlights was a double elimination cornhole tournament! Allen was very responsive and made us feel welcome. We would like to return sometime.
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

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

Fantastic House with Great Amenities

House was great. Beautifully kept and well equipped for guests with 2 fridges and plenty of storage space in the kitchen. So much to do between the kayaks and crab traps! As the description provides, the internet is very spotty so streaming shows, particularly at night, was impossible. Hope to return!
Stayed 7 nights in Jun 2020
Response from VrboOwner on 19 June 2020
Thank you so much. I'm glad you enjoyed some of the amenities. They are starting to install fiber for internet this summer. We are hoping this improves by sometime this fall.
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