Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock | House in Woolford

9.8 (75 Reviews) |   Pet Friendly   7 Bedrooms  5 Bathrooms  18 Guests
Woolford House | Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

7 Bedroom House in Woolford

5+ acres, private pool, wide water, sandy beach, dock, boats, firepit & bikes
Beautiful, newer custom 3-story home w/ wrap-around porches, 7 bedrooms & 5 baths & can accommodate up to 18 guests*. The 3rd floor is a haven for kids with a game room, two bdrms & a bath.
Close to town, yet your own, secluded compound for extended family & friends.
Gorgeous upscale neighborhood just 10 mins from Cambridge & Easton MD.
A perfect retreat with massive entertaining areas.
Family retreat perfection!
"Saddle Beach", our fabulous, newer waterfront owner’s home is on 500 feet of private Chesapeake waterfront.
It’s a grand vacation home with idyllic wrap around porches, your own private pool, dock, beach and pond. It's just 10 minutes from the renowned Hyatt Chesapeake Bay Spa and Resort, countless restaurants and quaint shops and, if it suits you, less than an hour from Ocean beaches.
'Saddle Beach' is on Dorchester County's exclusive McKeil Point neighborhood on the Little Choptank river, just off the Chesapeake Bay. The property has a mile-wide view and a 200' dock. The home is exceptionally furnished, with 4200sf of living area with another 1200sf of open and screened porches.
6 bedrooms and a sleeper den with sofa-bed and bath with walk-in shower. A large eat-in kitchen, two full size refrigerators, massive open entertaining area with 3 living rooms and a study. The 3rd floor is designed for kids with a recreation area, wide dormers, a full bath, and two bedrooms with 8 beds. An in-ground pool is off the porch & the home has beautiful millwork and exotic, reclaimed hand-cut wide-plank walnut floors. A lovely tidal pond is just off the living room.
The Property:
The perfect Family Retreat!
Gorgeous wrap around porches include a screened outdoor eating area overlooking the pool. The compound was designed as an owners' dream, and includes a pool, ample decks for entertainment, a gorgeous beach, private natural setting, and walkways to the adjacent marsh. Towering pines, aromatic cedars, and marsh grasses dot the landscape. There is a rustic tidal pond next to the house providing rest for swans, ducks, & geese. The dock stretches 200 feet into the river with 3 berths for boats and seating for your enjoyment. Wildlife abounds; you may find yourself crabbing and fishing all day. Yes, our crabbing is excellent!
The unique, secluded neighborhood consists of a single, mile-long road on its own peninsula with Dorchester's finest homes, stretching far into the Little Choptank River. The quiet street invites scenic bike rides or long walks to watch the sunsets.
Mosquito Control measures provided for your comfort,
The Area:
A local country store, restaurant and boat ramp is 5 minutes away and the Chesapeake Bay, with its fishing, cruising, and endless sunsets, is out your window.
The town of Cambridge is ten minutes away, with a pre-civil war, Victorian inspired downtown, and countless restaurants and shops. It’s not much further to visit the Maryland towns of Oxford, Easton, or Saint Michael's to walk the streets, take in the restaurants, or visit art shops and galleries.
On the property, relax! Go no further than the shoreline to find great swimming, crabbing, fishing, sunning, or boating. The sandy beaches are a luxury all year long, and the heated pool provides for a warm swim during those colder days and nights in May and September/October**. Endless porches and a stone fire pit is the centerpiece for many nighttime get-togethers.
In the neighborhood, bike or walk down the neighborhood's 'private' peninsula and enjoy marvelous sunrises and sunsets among the finest of Maryland's summer and weekend retreats.
Sports both on water and land.
Fishing Creek provides wide, almost endless passages for quiet kayaking, fishing, or pleasure boating. The waterskiing is excellent. The other side of the peninsula faces the Chesapeake Bay and Madison Bay and provides an open door to sailing or to the many top fishing spots.
In town, there are boats to rent for a sail on the Choptank. Bike tours from all over the world flock to the eastern shore because it is flat, the roads are good quality, the traffic is light, and the sights are endless. Blackwater Refuge offers world-class nature views, and you can also bike in Easton, Saint Michaels, and Oxford, and there are many bike tour maps available to the visitor.
There are two fantastic golf links nearby. The River Marsh course at the Hyatt Chesapeake is renowned. Hog Neck (18 miles) has a four-star rating from Golf Magazine. There are three additional courses between starting just nine miles away.
"Hot Tub" as listed is a Jetted Jacuzzi tub in the Master bath. We have a Steam Shower as well.
* - Additional charge for groups larger than 14
** - Pool heated *only* in May and between mid-September and closing for a fee
** - Pets: One (1) dog (only) is permitted with a required pet fee and refundable pet deposit during any stay. All pet signs including hair waste etc. must be removed by the guest.
** - Outdoor (only) security cameras face the driveway and water

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock is located in Woolford. Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock provides accommodation, featuring Pet Friendly, Pool, TV, among other amenities. This House features Pet Friendly, Pool, TV, to make your stay a comfortable one.

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock has 7 Bedrooms , 5 Bathrooms, and max occupancy of 18 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
Pet Friendly
Pool
TV
View
Private Pool
Ocean View
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Spa
Fireplace/Heating
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Toilet paper
  • Jetted bathtub
  • Towels provided
  • 5 bathrooms
  • Bathtub or shower
  • Shampoo
  • Soap
  • Hair dryer
Bedroom
  • 7 bedrooms
  • Bed sheets provided
  • Sofa bed
  • Dining table
  • Living room
  • Fireplace
  • Dining room
Kitchen
  • Refrigerator
  • Stovetop
  • Dishwasher
  • Coffee/tea maker
  • Oven
  • Toaster
  • Microwave
  • Cookware/dishes/utensils
  • Lobster/crab pot
Laundry
  • Laundry facilities
  • Washing machine and dryer
  • Near laundromat
Ocean view
  • Beach towels
  • Beach sun loungers
  • On the beach
Parking
  • Onsite parking
  • Car required
Pet Friendly
  • Welcoming dogs only
  • 1 total (up to 50 lbs per pet)
  • Pet friendly
Accessibility
  • Smoke-free property
  • Note from host: We take this seriously, thanks
Activities
  • Fitness facilities nearby
  • Golf nearby
  • Golf privileges
  • Cycling nearby
  • Golfing on site
  • Kayak on site
  • Birdwatching nearby
  • Swimming nearby
  • Winery tours nearby
  • Hiking/biking trails nearby
  • Casino nearby
  • Bicycle on site
  • Water sports equipment
  • Horse riding nearby
  • Boat on site
  • Tennis on site
  • Jet skiing nearby
Entertainment
  • DVD player
  • Stereo
  • Arcade/game room
  • Table tennis
  • Games
  • Smart TV with cable/satellite service
  • Foosball table
  • Books
General
  • Unit size: 5400 sq ft (502 sq m)
  • English
  • Spanish
  • In a rural location
  • On the waterfront
  • Near a hospital
  • On the lake
  • Near the bay
  • Near outlet shopping
  • In the city center
  • Near a health or beauty spa
  • Office
  • Desk
  • Desk chair
Guest Services
  • Babysitting service available
  • Playground
  • Children's games
  • Children's toys
  • Children's books
  • Stair gate
  • Children's dinnerware
  • Chef
  • Concierge services
  • Local meal delivery service
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Balcony
  • Firepit
  • Barbecue grill
  • Dock
  • Fenced yard
  • Outdoor furniture
  • Garden
Security/Safety
  • First aid kit
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Deadbolt lock
  • Fire extinguisher
Spa
  • Fence around the pool
  • Heated pool
  • Sauna
  • Hot tub
  • Massages
  • Private pool
  • Outdoor pool

Policies

Check-in
Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 30
Check-out
Check-out before 10:30 am contactless check-out available
Child Policy
Children are welcome. note from host: love kids! house designed with a kids' floor!
Event Policy
No events allowed;only small, indoor parties
Pet Policy
1 total (up to 50 lbs per pet) note from host: must ask at booking. a fee plus deposit required. pets allowed restrictions apply; for more information contact the property at the number on the booking confirmation service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy
Smoking is not permitted;we take this seriously, thanks

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 carbon monoxide detector on the property host has indicated there is a smoke detector on the property note from host: only small, indoor parties 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 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

Linda S.
Aug 25, 2025 01:01:53 AM
Review Score:   10
Summary: We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family.
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