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A Beautiful Waterfront Retreat for Family Gatherings!

Photo gallery for A Beautiful Waterfront Retreat for Family Gatherings!

Oyster Bar @ Mallard Cove
Exterior
Evening sunsets from the front of the house
Interior
Rainbows over Church Creek

Reviews

10 out of 10
Exceptional
6 bedrooms3+ bathroomsSleeps 12353.0 sq m

Popular amenities

  • Parking available
  • Hot tub
  • Dryer
  • Washer
  • Fireplace

Explore the area

Map
Woolford, MD
  • Harriet Tubman Underground Railroad National Historical Park
    ‪14 min drive‬
  • Harriet Tubman Museum and Educational Center
    ‪18 min drive‬
  • Choptank River Lighthouse
    ‪20 min drive‬
  • Cambridge, MD (CGE-Cambridge - Dorchester)
    ‪22 min drive‬

Rooms & beds

6 bedrooms (sleeps 12)

Guest Room - Main Level (King)

1 King Bed

Guest Suite - Main Level (Twins)

2 Single Beds

Master Suite - Main Level

1 King Bed

The Loft

1 Double Sofa Bed

The Orange Room - (Twins)

2 Single Beds

Upper Level - Queen Suite +Twin

1 Queen Bed and 1 Single Bed

3 bathrooms, 1 half bathroom

Main Level - Full bath (Guest Suite)

Towels provided · Bathtub or shower · Toilet

Main Level - Powder Room

Toilet

Master Suite

Towels provided · Bathtub · Toilet · Shower only · Jetted bathtub · Hair dryer

Upper Level Full Bathroom

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Separate dining area
Garden
Dining area

About this property

A Beautiful Waterfront Retreat for Family Gatherings!

Come take a break with your extended family and friends to a remote area of Dorchester County, Maryland. With 2.5 acres and plenty of waterfront, there is ample ways to enjoy all the property has to offer and the beautiful scenery. Enjoy the pool (May thru September - Not heated) or swim in the protected Mallard Cove. Catch crabs or fish off the dock or explore the water views on 2 provided kayaks. It is a perfect getaway! The outdoor space includes a saltwater pool, deck for sunbathing and dining, screen porch, extended dock and plenty of lawn for family activities. Enjoy the outside fire pit, wood burning fireplace in the family room, or the gas fireplace in the living room overlooking Mallard Cove. You can be assured that the property will be properly cleaned and sanitized.

Property manager

Tom Hutchinson

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Pet-friendly

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Welcome to Cherry Point

Waterfront Family Retreat with Pool on 7+ acres!

  • Pool
  • Kitchen
  • Washer
  • Dryer
10.0 out of 10, (54 reviews)
Waterfront Family Retreat with Pool on 7+ acres!

House Rules

Check in after 4:00 PM
Minimum age to rent: 35
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
Excludes Doberman, Rottweiler, and Pit Bull breeds
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Smoking

Smoking is not permitted
No glassware on the deck, pool area, or in the pool
No parking in the garage
Owner requires a short-term lease agreement and a security deposit of $1000 when the Property Protection Plan is selceted.

Important information

You need to know

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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

A car is required for transport to and from this property

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 Choptank River Lighthouse are local landmarks, and some of the area's attractions include Richardson Maritime Museum and Ruark Boatworks. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Woolford, MD

What's nearby

  • Harriet Tubman Underground Railroad National Historical Park - 14 min drive - 12.5 km
  • Harriet Tubman Museum and Educational Center - 18 min drive - 16.7 km
  • Choptank River Lighthouse - 20 min drive - 17.5 km
  • Long Wharf Park - 20 min drive - 17.7 km
  • Gerry Boyle Park at Great Marsh - 22 min drive - 18.9 km

Getting around

  • Cambridge Station - 22 min drive
  • Easton, MD (ESN-Easton - Newnam) - 43 min drive

Restaurants

  • ‪Carmela's Cucina - ‬16 min drive
  • ‪Woolford Country Store - ‬5 min drive
  • ‪La Bella Pizzeria - ‬16 min drive
  • ‪Bombay Tadka - ‬16 min drive
  • ‪Lindy's Seafood - ‬4 min drive

Frequently asked questions

Does A Beautiful Waterfront Retreat for Family Gatherings! have a pool?

Yes, this property has an outdoor pool.

Is A Beautiful Waterfront Retreat for Family Gatherings! pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.

What time is check-in at A Beautiful Waterfront Retreat for Family Gatherings!?

Check-in begins at 4:00 PM.

What time is check-out at A Beautiful Waterfront Retreat for Family Gatherings!?

Checkout is at 10:00 AM.

Where is A Beautiful Waterfront Retreat for Family Gatherings! located?

Situated on the waterfront, this holiday home is within 9 miles (15 km) of Blackwater National Wildlife Refuge, Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman State Park Visitors Center. Christ Rock Park and Snows Turn Park are also within 9 miles (15 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. 23 out of 23 reviews
Rating 8 - Good. 0 out of 23 reviews
Rating 6 - Okay. 0 out of 23 reviews
Rating 4 - Poor. 0 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Robin W.

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

Great property

We had a great time. The kids had a blast. The dock and the pool were amazing. It was a hot week so the pool was a lifesaver. Would definitely recommend
Stayed 7 nights in Jul 2024

10/10 Excellent

Sean O.

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

Fantastic family stay

We had a wonderful time at the half shell, the kids loved the pool, crabbing and fishing from the dock, kayaking and exploring the area. we enjoyed having a quiet relaxing week, disconnected but an easy drive for groceries or food. tom was a great host, the house was in perfect shape with plenty of things to keep the little ones occupied. the huge yard was amazing for the the dogs and kids run around. we look forward to seeing tom and the half shell again next year!
Stayed 8 nights in Jun 2024

10/10 Excellent

Verified traveller

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

Heaven on Earth

My family and I had a week long vacation together and this was the perfect place for it! We enjoyed the dock, kayaking, and the pool! Grocery store and country market close by. The Maryland crabs were awesome and plentiful. The house was the perfect set up, clean, high quality and met every need for all. Tom was an exceptional host, very kind and extremely accommodating. By far our favorite vacation together! Thank you Tom for hosting our family and your kindness and generosity!
Stayed 7 nights in Jul 2024

10/10 Excellent

Melanie M.

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

A slice of paradise

Perfect stay from beginning to end. Cooks kitchen perfect for our group. Lovely house and pool. We’ve stayed two years in a row and can’t wait to come back in 2024. Thank you Tom for everything!!!!
Stayed 6 nights in Aug 2023

10/10 Excellent

Tracy C., Palmerton PA

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

Best Vacation!

This home is amazing! We had a big family group stay here and so many memories were made. The home is just like advertised-plenty of space for all of us. Tom-the owner-made sure we had everything we needed and answered all of our questions. The home, the pool and the dock were all clean and well maintained. So many extras included! Also, close to a couple of towns so lots to do and great places to eat. We would definitely stay here again.
Stayed 7 nights in Jul 2023

10/10 Excellent

Robin M.

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

What a relaxing vacation!

This lovely house provided us with everything we needed for a perfect vacation. The house was beautiful and well equipped. Enjoyed the pool every day, kayaked and rented a boat for 3 days to enjoy the lovely views on the river. Watched the ospreys feed their young and had numerous turtles visit us in the yard. We took advantage of the crab traps which our 9 year old grandson loved checking on a daily basis. Ended the week with a crab fest from a local seafood store! Thank you, Tom, for sharing your home with us!
Stayed 7 nights in Jun 2021

10/10 Excellent

Amy S.

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

Amazing!

The pictures do not do this house justice! The house was very clean, well stocked for anything a cook would need, the location was so quiet and it was just paradise! If you have multiple families, they can stay in their own areas of the house for sleeping arrangements. You can watch beautiful sunrise while sitting on the deck, in the pool or in the sunroom! You can watch storms roll in or roll out over the bay! We caught and released crabs using the cages that Tom provides. The pool was so nice, warm and relaxing even in the 99 degree weather! There are some many local businesses close by that you can easily support them, Lindy’s Seafood, Emily’s Produce, Bay County Bakery and Simmons Grocery Market. The Half Shell definitely will not disappoint you and Tom was an amazing host! He answered all my questions promptly! Thank you so sharing your beautiful home!!
Stayed 8 nights in Jul 2023

10/10 Excellent

Artise S.

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

Perfect Escape

The Half Shell property was more than we had hoped for! Tom really has thought of everything here---everything you would need for cooking- including pots, burner, and propane for cooking crabs (which you can catch right off the dock or pick up at Lindy's down the road) and for shrimp boils. We cooked most of the nights here and enjoyed the lawn games provided while cooking and enjoying cocktails. We all (kids, teens, and adults) loved spending time by the pool. There is a wonderful shelf in the pool where you can have your feet in while sitting in the pool chairs! It was perfect for lounging while the kids swam. We traveled with 3 separate families and there was more than enough room for everyone. Other wonderful amenities: provided pool towels, on site washer/dryer, crabbing traps and lines, large dining table so everyone can eat together (back deck and inside), and fishing rods on site. Tom was very quick to get back to us on anything we needed or questions we had---we even had wonderful suggestions for where to view the Cambridge 4th of July fireworks! This was a perfect escape, beautiful house, and a backyard/pool area that we were all sad to leave.
Stayed 7 nights in Jul 2023

10/10 Excellent

Debbie T.

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

Half Shell Stay Added Up to a Whole Bushel of Fun

The house and property were exactly as described and out-fitted, offering our multi-generational, active adult family plenty of space to relax, play, sleep, eat, and enjoy the sunrises beyond the dock and across the bay. Bedrooms were varied in set ups and spread out to provide privacy and quiet for (ugh) virtual workspace. The kitchen was big and well stocked with cooking and serving items. The large island with extra small sink was perfect for communal food prep, cocktail mixing, and misc. storage. The casual family room was cozily, comfortable for rainy day movie watching and the living room overlooking the deck was an ideal place to escape the sun for a bit and still watch the bay. Early morning kayaking on the placid water in multiple directions was serene and offered lovely views and solitude. Board games, yard games, the pool with Baja shelf, the fire pit, and crabbing/fishing entertained everyone. The wonderfully landscaped and fenced pool area was perfect for our pup. Tom, the host, was lovely, responsive and provided brochures and local info. as part of a perfect welcome basket. Aside from grocery shopping , there was not too much need to find outside activities, but some of our family off-site favorite destinations were the Blackwater Wildlife Refuge, Liddy's Seafood (just around the corner), Emily's Produce (fresh and local and multiple activities for kiddies), RAR Brewing, and some local downtown shops. Minor detail, but used the majority of the time by everyone and throughly enjoyed... the outside shower. We highly recommend the Half Shell!
Stayed 7 nights in Jun 2021

10/10 Excellent

Kathi H.

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

Fun Family Time!

Tom was a terrific host and the home is even better than in pictures/description on VRBO. KITCHEN FULLY STOCKED! We were able to cook full meals for the family just like at home--every type of cookware, utensil, and small appliance we needed was there and paper towels, foil, plastic wrap, and plastic containers. Cook inside on the stove or in the oven/microwave or outside on the grill (or s'mores on the firepit). Plenty of cleaning supplies, good dishwasher. BEDROOMS Primary BR is huge as is accompanying full bath. Gorgeous views to start your day or sleep in on the comfortable king bed. Two upstairs BRs. Zero complaints from our younger kids about the beds! Entry level BRs private--older kids stayed there and could sleep in without being bothered by the younger kids. They are smaller rooms; comfy beds and bedding. BATHROOMS All quite clean and functional. The primary BR has a full; the upstairs BRs have a full; and the entry level BRs have a full. And there is a powder room on entry level. OTHER We used the family room off the kitchen when we were inside (why be inside??). We did not use the formal dining room or living room but they are sizable with good furniture. The screened in porch was perfect for getting out of the sun and doing crafts or reading on the nice chair or loveseat. OUTSIDE This is where you will want to be. The pool was great--clean and with a nice walk in so you could actually sit on chairs with your feet in the water (the chairs are there). Do your part to skim and run the pool vacuum and you'll have a pristine pool like we did. The the dock was perfect for morning coffee and to check the crab traps--we had crabs every day, though we released them as most were undersized (but the dog loved to investigate). The younger kids fished from the pier and kept a close eye on the osprey family living adjacent. There is a small break along the bank to put in kayaks--super easy (and there are two excellent kayaks there with paddles and life vests). And the yard was perfect for frisbee, playing catch with the rugby ball or football, croquet, or chasing the dog! The dog also got into the water at the kayak put-in. You really cannot swim in hot months unless you're pretty brave about jellyfish. MISC Laundry works well (and detergent there). Plenty of bath and beach towels. Super quiet neighborhood. Eat seafood from nearby Lindy's and Emily's for produce/meat/cheese/beer. In town, go to Blackwater Bakery, RAR, Snappers. And mostly, RELAX
Stayed 7 nights in Aug 2022

10/10 Excellent

Natalie K.

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

Relaxing family vacation

We had a wonderful week swimming and fishing/crabbing off the dock. We brought jet skis and parked them on the dock for the week. The house was clean and the kitchen was well-stocked. We cooked most meals at the house but ordered steam crabs from Lindy’s one night. Everything was wonderful and we would highly recommend. Tom was easy to get a hold of and very accommodating.
Stayed 7 nights in Jul 2022

10/10 Excellent

Melanie M.

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

Slice of Paradise

I wish VRBO had 10 stars because this property was a definite 10!!! Gorgeous!! We all enjoyed our time at the Half Shell. Thanks for sharing your amazing home with all of us.
Stayed 7 nights in Jul 2022

10/10 Excellent

Roberta S.

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

great vacation

tom’s house is beautiful, comfortable, clean, and was easy for all 9 of us (ages 1 year to 67 years) and our dogs to navigate. the pool is lovely, with a shallow entry area that was extended out enough for our one-year grandchildren to be on, enjoy the water, and have fun (supervised of course) and the pool area is beautifully landscaped with a lovely view of the lake. in the pool area we also made s’mores over the fire pit. we barbecued several nights. the amenities were great. the view from every part of the house was fantastic. we had so much fun on our vacation, making wonderful memories with our children and grandchildren.
Stayed 7 nights in Jul 2022

10/10 Excellent

Sarah D.

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

So peaceful!

Nothing but positive feedback from our multi generational group. The checkin process was easy and very good communication with the owner. The house was *absolutely* spotless. Great views over the water, from inside and outside. Crabbing off the dock was great, and kayaking around the coves was SO peaceful. The landscaping around the yard and pool was so well done and added nicely to the pretty views. The layout of the house works so well, as described in other reviews. The kitchen was well stocked with high quality cookware and we loved the extra beverage fridges. It feels like the house is in the middle of nowhere (just what we wanted) but is actually extremely convenient to whatever you need. Cambridge, with Walmart and other “big box” stores, is only 15 minutes away. BUT, we happily did most of our shopping at Emily’s Produce. The Woolford General Store was also a favorite.
Stayed 8 nights in Jul 2022

10/10 Excellent

Julia D.

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

A wonderful vacation!

We had an incredible time at this beautiful home. The pool was so perfect for the kids. Tom was so helpful and a wonderful host. We’ll absolutely be back again!
Stayed 7 nights in Aug 2021

10/10 Excellent

Daniel R.

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

Great Chesapeake experience

Beautiful and impeccable property. Pool and dock are amazing. Fire pit was lovely and crabs literally walked into our traps. Well appointed kitchen. Layout is ideal for groups of families as there are three “wings” of 1-2 bedrooms each with a bathroom. All in all great stay. Thank you Tom!
Stayed 7 nights in Aug 2021

10/10 Excellent

Esther L.

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

Beautiful Retreat

The property was immaculate, spacious, quiet, and everything was well maintained. The communication between the property owner and me was prompt and efficient. The pool was beautiful and large. I would recommend this property for a large family who enjoy a pool, grounds and a lovely home.
Stayed 7 nights in Jul 2021

10/10 Excellent

Verified traveller

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

Family Vacation 2021

Our family group of six, ranging in age from 10 to 76, had a wonderful week. The property is way better than advertised. Beautiful, spotless, comfortable and supplied with all the extras you need to fully enjoy it. Crabbing, kayaking, relaxing, cocktails in the pool (plastic glasses, of course!), charter fishing nearby, resident osprey and the best home office anywhere if you can’t leave work behind. The owner/manager, Tom, is very easy to communicate with and prompt. He clearly wants you to enjoy a home he loves. Too many positives to list. The only negative was leaving after our week ended. Ray V, Shepherdstown, WV
Stayed 7 nights in Jul 2021

10/10 Excellent

Dorothea

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

WOW!

The week we spent here was wonderful! Our family planned this trip months ago and I cannot say enough about the house, the pool and the property overlooking Church Creek. The house was clean, and the gourmet kitchen looking out onto the water was well stocked! Everyone loved having some separate spaces that you could curl up with a good book or have family game night. The pool was so nice to have, especially in the summer. We paddle boarded, kayaked, and crabbed. Tom was great and always responded to our questions. If you are looking for chill time on the eastern shore with lovely views of the water and tranquilty, this is the place for you!
Stayed 7 nights in Jul 2021

10/10 Excellent

Trisha T., Glen Ridge, NJ

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

Gorgeous Waterfront Pristine Home

The words modern and immaculate are not usually paired with warm and inviting but those are the words that describe this perfect waterfront property. Our family enjoyed every inch of this beautiful home. It was well stocked with anything you could possibly need and so very organized! We loved having multiple gathering areas, the very comfy beds with great linens and the fantastic chef's kitchen with a 6 burner stove. The kids loved fishing and crabbing right from the dock and also swimming in the saltwater pool. The provided kyacks were a big hit and we enjoyed gathering around the fire pit in the evening. The home is also beautifully landscaped with lots of blooming flowers. We rented a boat one day and explored the surrounding waterways accompanied by dolphins at one point. We highly recommend going to the nearby Harriet Tubman Underground Railroad National Historic Park as well as The Black Water Refuge where we were greeted by a beautiful bald eagle in flight. Emily’s Market and Lindy’s Seafood are also great and very close by. We even popped over to Assateague National Seashore to see the wild ponies and had dinner one night in quaint St. Michaels. Tom was great with communication and was a perfect host. We look forward to returning soon
Stayed 5 nights in May 2021

10/10 Excellent

Joshua R., Kensington, MD

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

Fantastic stay

We had a wonderful stay at this property. The house is gorgeous and was spotless. The house owner was friendly, communicative, and made the process seamless. Pool was well-maintained and the grounds and amenities made this stay perfect for keeping active while socially distanced. Crab pots, pool towels, kayaks, fire pit—everything was waiting and ready. We had a wonderful time. Will definitely return.
Stayed 7 nights in Aug 2020

10/10 Excellent

Cari G., Baltimore MD

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

Relaxing waterfront retreat

Such a beautiful and well thought out house! Lots of space to accommodate gaming, playing games, watch sports or quietly reading a book. And if you have a boat it is a great place to explore to fish, crab or quietly enjoy nature. I highly recommend this house.
Stayed 7 nights in Aug 2020

10/10 Excellent

Al T.

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

Great stay

We wanted a remote home that allowed dogs, had a lovely pool, and included some activities, and we got exactly that. Check in was easy, and we were welcomed by some treats, which the owner provided, plus an amazing view of the bay/cove. We had an enjoyable time crabbing, swimming, and kayaking, and we never had to leave the property. Everything was provided for us, including towels and all of the crabbing equipment and bait/fish. The owner is very responsive, which we found out as we endured a mini-hurricane while we were there! Life is an adventure. We always had access to him through text and phone.
Stayed 10 nights in Aug 2020

About the host

Hosted by Tom Hutchinson

Host profile image
I grew up in the beach town of Stone Harbor, NJ. I love the water and the changing tides. I've owned the home since 2003 when it was a part-time, weekend property. I moved permanently from Baltimore, MD to Dorchester County in 2010 and have been a full-time resident ever since. I have enjoyed renovating every aspect of the property and house over the years and I am very vested in Dorchester County. I enjoy and support the community and have been very active in various groups. I enjoy swimming, biking, and running and either participate in or volunteer for our local Ironman 70.3 Eagleman and Ironman Maryland annually.

Why they chose this property

You can easily bring a large family and man’s best friend to enjoy the property without ever leaving. Relax, swim, exercise, crab, fish, walk, run, bike onsite and right out the door or just do nothing. And if you do want to get away, you can take a long car ride and see many beautiful areas of Dorchester County like the Black Water Refuge for bald eagle sightings or visit historic Cambridge which has a quaint downtown with shops, ice cream, plus restaurants, and bars.