Waterfront Family Retreat with Pool on 7+ acres! | House in Woolford

10.0 (63 Reviews) |   10 Bedrooms  5 Bathrooms  24 Guests
Woolford House | Waterfront Family Retreat with Pool on 7+ acres!

10 Bedroom House in Woolford

Looking for a place to really enjoy nature, boating, fishing, swimming, family games, campfires and more? Bring your boat! Bring your whole family! Cherry Point Vacation Rental is recently under new ownership and the owners aim to make this vacation the best ever!
The picturesque 7.4 acre property can be all yours for the week and includes a deep-water slip, sandy beach (when the tides out) and a floating dock, along the 1,200 feet of waterfront. Eagle, osprey, heron, hawks and waterfowl are as common as the sunrises. The grounds at Cherry Point include an older tennis court: perfect for tennis, basketball, hockey, roller skating and more; a 32’x16’ in-ground swimming pool (surrounded by decking, tables, lounge chairs and some pool toys); and lots of open space on the property with a large field for softball, soccer, badminton, horseshoes, and more including some wooded areas and private little sandy beaches for exploring and relaxing.
Cherry Point is perfect for multi-generational family getaways or multi-family vacations. There is a large main house (the original portion of the main house dates to 1919, featuring unique wood trim, beautiful old wood floors and some unique historic features...) and a newer updated addition which was added in the 1990's. And, if you need more room, there is additional living space we refer to as the "Annex" or “cottage” space with 3 bedrooms, a full bath, and large living area on the 2nd floor of the detached garage, overlooking the pool and water views.
The main house contains 7 bedrooms, 4 1/2 baths, living room with fireplace, den with fireplace, kitchen and dining area for group dining and family CRAB FEASTS, laundry, and screened porch with outdoor furniture and an additional picnic table, overlooking the water. The large Master Suite includes a 2nd floor deck overlooking the water. The new (2020), fully equipped kitchen, includes an induction electric cooktop and range, dishwasher, microwave, 2 refrigerators, drip pot coffee maker, Keurig coffee maker, blender and tons of kitchen accessories.
The "Cottage" is above the garage, overlooking the pool and has 3 bedrooms: one with 2 bunk-beds (sleeps 4 ), one with a queen bed, and one with 2 twin beds...along with a large family room and a full bath.
All rooms at Cherry Point are air-conditioned via central air, or window units.
This destination property offers swimming, fishing, crabbing, boating, dining and relaxing all in true maritime atmosphere of the Eastern Shore of Maryland! Watch the boats go by while dining alfresco or sitting by the pool! We include the use of canoes and kayaks, as well as stand up paddle boards during your stay.
There are many shops, restaurants and boutiques in the quaint maritime town of Cambridge which is about 15 minutes away. Cambridge is filled with history and unique out-of-the way sights. Travel through the countryside which James Michener wrote about in "Chesapeake" and let it take your breath away. Also, there are many seasonal events worth checking out in the area. Several golf courses and wineries are local. The world renown Hyatt Regency waterfront golf course is nearby and is open to the public. Harriet Tubman Underground Railroad National Historical Park and other underground railroad sites are a short drive, and the Blackwater Wildlife Refuge is our nearby neighbor and offers paths for walking, hiking, biking and more and also adds additional waterways for canoeing and kayaking.
Grocery stores in Cambridge include numerous options such as Food Lion, and Walmart and the local Simon's market. Excellent seafood everywhere you turn. The local Woolford general store is about a mile away. Slaughter Creek Marina just 10 minutes down the road. Buy fresh and mostly local produce, meats, eggs and flowers, crafts and more at the Cambridge Farmers Market every Thursday from 3-6 pm from May thru October at Long Warf in Cambridge near High and Water Streets. The Dorchester County Tourism Dept. operates out of the award winning Visitor Center at Sailwinds Park in Cambridge. There are exhibits, a playground, a beach area, a monument fountain, restrooms, a native garden, and a mile long boardwalk to stretch your legs. Check their website for local events!
Linens and towels are provided for your convenience.

Waterfront Family Retreat with Pool on 7+ acres! is located in Woolford. Waterfront Family Retreat with Pool on 7+ acres! provides accommodation, featuring Sports/Activities, Wellness Facilities, Fireplace/Heating, among other amenities. This House features Sports/Activities, Wellness Facilities, Fireplace/Heating, to make your stay a comfortable one.

Waterfront Family Retreat with Pool on 7+ acres! has 10 Bedrooms , 5 Bathrooms, and max occupancy of 24 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Woolford has interesting places to visit. If you want to learn more about the House in Woolford, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
Pool
TV
View
Private Pool
Ocean View
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Policies

Check-in
Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 29
Check-out
Check-out before 10:00 am contactless check-out available
Child Policy
Children are welcome. note from host: there is a pool and open water nearby.
Pet Policy
Pets not allowed

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 host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

Shea G.
Aug 25, 2025 07:05:29 PM
Review Score:   10
Summary: 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!
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