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Country Waterfront Estate Featured in Chesapeake Life Magazine

Bedrooms 10
Half Baths1
Space 3,700 sq. ft.
Property type estate
Minimum Stay 2 nights


About the property

The perfect setting, accommodations and amenities for large family gatherings

Cherry Point is a multi-generational family vacation estate on the Chesapeake Bay. The 7.4 acres includes a deep-water slip, sandy beach and a floating sports dock along the 1,200 feet of waterfront. Eagle, osprey, heron, hawks and waterfowl are as common as the sunrise. The well-tended grounds include a lighted tennis court and a 32’x16’ in-ground swimming pool. The deck surrounding the pool is furnished with deck chairs, lounges, umbrellas, a picnic table, lunch table, water toys, and a gas barbecue grill. The large athletic field is perfect for softball, soccer or other group activities.

The main house contains 7 bedrooms, 4 1/2 baths, living room with fireplace and library, dining room with fireplace and a large table for group dining, family room with library, electric fireplace, laundry and large screened porch. The fully equipped kitchen includes an electric range, dishwasher, 2 microwaves, 2 refrigerators, toaster oven, coffee maker, toaster, coffee grinder & blender.

The Annex has 3 bedrooms, (one with 2 bunk beds, one with a double and one with 2 twin beds), a family room with a ping-pong table and a full bath. We have one a high chair, a crib and stair guards for toddlers. All rooms are air-conditioned via central air or window units.

In addition to the many land-based activities, the water sports are extremely popular. We include the use of 2 kayaks, a canoe, and our unique SurfBikes during your stay. The SurfBikes can be used in a number of configurations to accommodate guests of all ages.

Cherry Point rentals are limited to extended family gatherings only and our rental license does not permit weddings, (sorry).

Keywords: family vacation, waterfront, 10 bedrooms, tennis court, swimming pool, large family, waterfront estate, softball field, family reunion, air conditioned

More Details

Michael Motsko
Member since: 2002
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
August 5, 2017

About Michael Motsko

Both Susan and I grew up in families that took 'family vacations.' We wanted our kids and grandkids to have the same kind of vacation but with 22 of us we could not afford the resorts. We found and bought this old 2-bedroom farmhouse on a SPECTACULAR piece of land, rebuilt it to fit our purposes and have been able to enjoy watching the grandkids become very close with each other even though they live from NJ to SC. Our long time renters have enjoyed the same benefit as they bring their extended families together for a vacation week at Cherry Point

Michael Motsko purchased this estate in 1991

Why Michael Motsko chose Woolford

We sail; Cruising the Chesapeake is the bible of the Chesapeake sailer and they said that Cherry Point is one of the finest anchorages on the Chesapeake. I learned that Cherry Point was for sale and bought it the day before the great-grandson of a previous owner arrived from Chicago to purchase it.

What makes this estate unique

Family tennis tournaments, 3 generation street hockey games on the tennis court, frizbee golf, using the metal-detector down where McKeel's dock was used to unload materials taken from captured British ships, searching for indian artifacts, enjoying the Blackwater National Wildlife Sanctuary, etc.

Guestbook comments from the owner

We had an family reunion vacation at Cherry Point and were delighted with the property. It had something for all ages. The pool was the focal point for many, but others played tennis, used the surfbikes, (great fun) or lounged on the private beach. The layout was perfect for the group of 23 and we used the Annex to house the teenagers. The highlight was the softball games and eating steamed crabs. It was a great place for the family to gather and we will do it again next year.
Aug 2012
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Woolford Estate Accommodation and Amenities

Property Type:
  • estate
  • Guests provide their own meals
Floor Area:
  • 3700 sq. ft.
House Rules:
  • Check-in: 3:00 PM / Check-out: 10:00 AM
  • Max. occupancy: 26
  • children welcome
  • pets not allowed ...
  • non smoking only
Location Type:
  • Beachfront ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Sports & Activities
  • Air Conditioning
  • Broadband Access ...
  • Clothes Dryer
  • Fireplace ...
  • Garage
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking
  • Parking for RV/Boat/Trailer
  • Telephone ...
  • Towels Provided
  • Washing Machine
  • Wood Fireplace ...
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils ...
  • Dishwasher
  • Ice Maker
  • Kitchen ...
  • Microwave ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • 5 Bathrooms
  • 1 Half Bath
  • Bathroom 5 - Full bath in Annex
    Shower - Hot & cold outdoor shower near pool
    Bathroom 6 - Powder room on first floor of main house
    Bathroom 1 - Full main house 1st floor handicapped accessible & equippe
    Bathroom 4 - Full - Main house 2nd floor
    Bathroom 3 - Full - Main house 2nd floor
    Bathroom 2 - Full - Master bedroom main house 2nd floor
  • 5 1/2 baths including a handicapped accessible & equipped full bath on first floor of the main house. There is an outdoor shower near pool.
  • 10 Bedrooms, Sleeps 26
  • Bedroom 2 - 2 twin/ single , Main house
    Bedroom 3 - 1 queen , 1 murphy bed , Main house
    Bedroom 10 - 2 twin/ single , Annex
    Bedroom 9 - 2 bunk bed , Annex
    Bedroom 8 - 1 queen , Annex
    Bedroom 4 - 2 twin/ single , Main house
    Master - 1 queen , Full bath & 8' x 12' balcony Main house
    Bedroom 5 - 2 twin/ single , 1 baby crib , Main house
    Bedroom 6 - 2 twin/ single , Main house
    Bedroom 7 - 2 twin/ single , Main house
  • Queen size Beds (2), Double Beds (2), Twin or Single Beds (12), Child Beds (1), Baby Cribs (1), Sleep Sofa or Futons (1), Bunk Beds (2)
  • Books ...
  • CD Player
  • DVD Player
  • Games
  • Ping Pong Table
  • Satellite / Cable ...
  • Television ...
  • Toys
  • VCR
  • Video Library ...
  • Balcony ...
  • Deck / Patio ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Tennis ...
  • Water Sports Gear ...
  • wheelchair accessible
Pool / Spa:
  • Private Pool ...
  • churches
  • cinemas
  • festivals
  • library
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • horseshoes
  • paddle boating
  • photography
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • fishing
  • golf
  • hiking
  • jet skiing
  • kayaking
  • pier fishing
  • rafting
  • sailing
  • snorkeling
  • sound/bay fishing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing


Excellent! 4.6/5 -
(8 traveler reviews)

75% Complete
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Country Waterfront Estate Featured in Chesapeake Life Magazine
average rating of 4.625 based on 10 reviews

I loved the place but pool was full of cardboard and glass even after cleaned by pool service .

  • 4 of 5

Loved it but pool needed cleaning and couldn't enjoy it til end of vacation. Also part of dock broke while teen boy walking across it .

  • Submitted: Aug 14, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Beautiful area, quaint house, needs some TLC

  • 3 of 5

We had a great time spending the weekend here to celebrate our grandfather's 80th birthday. There were 25 of us total, including quite a bunch of kids, and this property was able to house us all! The area is beautiful and we were able to enjoy the outside for a bit despite the weather being a little chilly and rainy. The dock/mini beach were perfect for the young kids to see snails, frogs, and baby jellyfish. We also were able to fish and canoe. It was great to have so many places to lounge and catch up with family members. I wanted to give this property 4 star, but it needs some work--some of the showers didn't work and while it has a ton of charm being so old, it needs a little sprucing up. The caretaker was delightful and so sweet--very easy to work with.

  • Submitted: May 8, 2017
  • Stayed: May 2017
  • Source: HomeAway
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Wonderful Experience

  • 5 of 5

My friends and I rented Cherry Point for a birthday celebration. We were a group 20+ folks ranging from mid-20s to early-30s. Swimming in both the pool and the Choptank were wonderful. The house was clean and spacious with a ton of character. The large property gives a sense of privacy. I am actively looking for an excuse to rent the place again. If you find yourself at Cherry Point make you sure you get up early enough to have coffee on the dock around day break.

Finally, the agent and the housekeeper were both very easy to work with and pleasant.

  • Submitted: Jul 8, 2016
  • Stayed: June 2016
  • Source: VRBO, from HomeAway
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Silver Spring

We enjoyed a slice of Heaven

  • 5 of 5

My family and friends have gotten together for 26 years. We are a group of 12 guys that always travel to different location each year. We have been as far south as Elizabeth City, NC and as far north as Marthas Vineyard, MA.

Our group travels from all over. We have members of our group from AZ, St. Martin, MA, NJ, OH, RI, MD, NH & VA

This was the best house that we have rented.

Everything was easy peasy. The rental process was smooth. The house was exactly as represented and more so. The large dining room table was great for our group. The screened in porch was an anytime gathering place for our group.

We arrived via a 40' sport fisherman with outboards. We tilted the engines up a little and we were always floating. We swam in the Little Choptank River and the outdoor pool. It was nice to be able to enjoy either one. Most of the guys enjoyed the clean waters of the Little Chop Tank River.

Our experience was joy, fellowship and relaxation and Cherry Point offered all of it for us.

Thank you, David

  • Submitted: Jun 7, 2016
  • Stayed: June 2016
  • Source: VRBO, from HomeAway
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Fantastic Family Retreat

  • 5 of 5

My family (of 22) which included my parents, siblings, spouses, nieces and nephews spent an incredible week at Cherry Point. There was so much to do, you couldn't possibly get bored, no matter the age. We ranged in age from 62 to 7months and everyone has said how much they loved the house (history everywhere you look), the view, the amenities and the peacefulness of the place. We would all love to spend more time at Cherry Point. Thank you for opening your house to us!!

  • Submitted: Aug 19, 2014
  • Stayed: August 2014
  • Source: VRBO, from HomeAway
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Wonderful location, perfect house for large gatherings!

  • 5 of 5

I was looking for a place to host a surprise 50th birthday for my husband, and Cherry Point was the perfect spot. there were 21 of us, and we fit very comfortably (with two rooms we actually did not use). We are an active group, and there was plenty to keep us busy - paddle kayaks were awesome, biking, tennis, softball and card games- something for everyone (it's a shame we missed the pool being open). The house is very quaint and obviously well loved, with a lovely family feel to it. The view is quite spectacular. We were welcomed by the housekeeper who showed us around and was very friendly and helpful. The owner was very flexible about arrival and departure times. All in all a great weekend in a beautiful spot. Hopefully we will be able to come back one day!

  • Submitted: Nov 13, 2013
  • Stayed: October 2013
  • Source: VRBO, from HomeAway
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Nearest Airport
100 Miles
Car: recommended

The Blackwater National Wildlife Refuge is just 11 miles away, but you will see plenty of wildlife without leaving Cherry Point. Eagles, osprey and heron fly by constantly. Marsh and red shouldered hawks work the marshes while deer and fox prowl the edges of pine forests. The water holds crabs, clams, oysters and 15 varieties of fish including flounder, sea trout, drum and the prized rockfish.


Rates & Availability

Taxes and fees are additional
This calendar has not been updated in over 2 months and the availability shown may not be accurate.

Additional information about rental rates

Refundable damage deposit $1,000

The rental rates include all taxes & fees as well as all linens & towels.

SPRING FALL: 1/2 of the Rental With Contract, the Balance of the Rental Due 60 Days Before Arrival Date.
SUMMER: 1/3rd of the Rental Fee With Contract, 1/3rd of the Rental Fee Due 60 Days Before Arrival Date, the Balance of the Rental Fee Due 30 Days Before Arrival Date.


Owner's Cancellation Policy

  • Canceled bookings will not receive a refund