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 Pool, Private Pool, Ocean View, among other amenities. This House features Pool, Private Pool, Ocean View, 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
  • Other
  • 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
Other Policy 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

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Reviews

Tasneem C. Dec 2, 2024 03:37:28 AM
Summary: Allen and Kathleen’s house was exactly what we were looking for. Water views. Spotless rooms and bathrooms. Perfect for our large family of 23. Well equipped and recently renovated kitchen with everything we could have needed for Thanksgiving dinner! Spacious rooms. Kitchen-dining was bright, sunny, warm, and cozy and perfect for our Thanksgiving dinner. We had a nice Thanksgiving fun run in the community. Tennis. Canoe rides. Fishing. Football watching in a cozy setting. A trip to backwater refuge and the Harriet Tubman visitor center plus golfing and a trip to the brewery in Cambridge. Fun was had by all! We couldn’t have asked for better. 🦃
Lan L. Sep 5, 2024 12:27:26 PM
Summary: 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
Kathleen W. Aug 21, 2024 10:37:13 PM
Summary: Wonderful place for a multigenerational family vacation. Enjoyed the pool, pickleball and lots of crabs.
Maria N. Aug 12, 2024 04:18:25 AM
Summary: 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!
Peg W. Aug 5, 2024 05:17:52 AM
Summary: Property met all of our expectations. We were a family of twenty from ages 8 to 76, three generations. Loved all the outdoor sports available really used the pool since our week was 90+ degrees everyday. Sunrise and kayaking every morning, more coordinated members paddle boarded. My grandson especially enjoyed kayaking, fishing, crabbing and exploring the property. Looking forward to next year. Only recommendation some free standing umbrellas at pool where lounge chairs are located. Shade was at a premium our week. Allen and Kathleen very conscientious hosts.
PG H. Jul 29, 2024 10:23:46 PM
Summary: 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.
David O. Jul 22, 2024 05:43:32 AM
Summary: 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.
Mary W. Jul 16, 2024 09:36:42 AM
Summary: 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.
Brent W. Jul 7, 2024 09:04:45 AM
Summary: 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.
Scott M. Jun 4, 2024 07:38:05 AM
Summary: We had an amazing time! We wanted a home on some property with lots of activities for the whole family. This home fit the bill perfectly. The overall beauty of the place was breathtaking, and all of the activities were enjoyed by the whole family. The kids LOVED the pool! Thank you for adding the solar blanket!! We also loved the location, as we were only a little over an hour from Ocean City Beach!! The owner communicated with us very well, and was very responsive when we had questions. Thank you for giving the Milford Family a vacation to remember!

FAQ's

Is this Woolford house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Woolford house have a swimming pool?

Yes, this Woolford house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Woolford house?

Best-rates for the Woolford house starts from $1,463 per night with includes Internet, View, Balcony/Terrace, Kitchen, Pool, Private Pool, Ocean View, Guest Services, TV, Bedding/Linens, Fireplace/Heating, Entertainment, Barbecue/Outdoor Cooking, Child Friendly, Laundry, Wellness Facilities, Air Conditioner, Parking, Other, Security/Safety, Sports/Activities with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

Is Woolford house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Woolford house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Woolford house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Woolford house?

Based on the information reported by the owner or manager, the Woolford house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Woolford house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Woolford house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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10.0 (50 Reviews)
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  • Air Conditioner
  • Parking
  • Pet Friendly