10BR House Vacation Rental in Woolford, Maryland

Vacation Rentals

Updated on Jun 22, 2020

Waterfront Family Retreat with Pool on 7+ acres!

Located in: Woolford
CONSIDERING COVID19 we will work with our guests if they find that they are unable to travel during their scheduled week. Rescheduling visits or cancellation after the deadline will be accommodated where possible.

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 make, 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 2 canoes and 2 kayaks, as well as our unique Surf-Bikes during your stay. The Surf-Bikes can be used in a number of configurations to accommodate guests of all ages.

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 including Food Lion, and Walmart . Excellent seafood everywhere you turn. Farmers markets are nearby, and a local general store 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!

During Summer Months, minimum rental periods of a full week Sunday to Sunday are preferred. This works best with trash collection in the area. Shorter stays can be requested and will be considered during off peak times. Linens and towels are provided for your convenience.
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