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Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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Reviews
9.89.8 out of 10
Exceptional
Entire home
Popular amenities
- Beach view
- Parking available
- Dryer
Explore the area

Woolford, MD
- Harriet Tubman Museum and Educational CenterPlace, Harriet Tubman Museum and Educational Center28 min drive
- Choptank River LighthousePlace, Choptank River Lighthouse29 min drive
- Long Wharf ParkPlace, Long Wharf Park29 min drive
- Easton, MD (ESN-Easton - Newnam)Airport, Easton, MD (ESN-Easton - Newnam)58 min drive
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About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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
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
During your stay at this holiday home, you'll be close to Ragged Island. You'll find features such as an outdoor pool, 1 hot tub and concierge services. The holiday home offers free WiFi and a private pool.
- Air-conditioned home with private pool, kitchen and washing machine
- Free WiFi
- Take a swim in the outdoor pool or soak in the hot tub
- Services include a concierge and babysitting
- On-site recreation includes tennis courts, a sauna and a playground
- 5.9 miles (9.5 km) from Blackwater National Wildlife Refuge and 8.9 miles (14.4 km) from Harriet Tubman Underground Railroad National Historical Park
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock offers its guests an outdoor pool, Access to hot tub, and a sauna. Barbecue grills, an arcade/games room, and a garden are also featured at the family-friendly Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock.
Property amenities
Beach
- On the beach
- Beach loungers
- Beach towels
Pool/Spa
- Heated pool
- Hot tub
- Massage
- Outdoor pool
- Private pool
- Sauna
Internet
- Available in the house: Free WiFi
Parking and transport
- Car required
- Parking on site
Kitchen
- Blender
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Electric kettle
- Hob
- Ice maker
- Kitchen island
- Lobster/crab pot
- Microwave
- Oven
- Paper towels
- Refrigerator
- Spices
- Toaster
Dining
- Chef service
- Dining table
Bedrooms
- 7 bedrooms
- Bedsheets provided
- Sofa bed
Bathroom
- 5 bathrooms
- Bathtub
- Bathtub or shower
- Hair dryer
- Shampoo
- Shower
- Soap
- Toilet paper
- Towels provided
Living spaces
- Dining table
- Fireplace
- Living room
- Separate dining area
Entertainment
- Books
- DVD player
- Games
- Smart TV with cable/satellite channels
- Stereo
Outdoor areas
- Balcony
- Barbecue grill
- Dock
- Fenced yard
- Firepit
- Garden
- Outdoor furniture
Laundry
- Laundry facilities
- Washing machine
Work spaces
- Desk
- Desk chair
- Office
Comfort
- Air conditioning
- Heating
Pets
- Pet friendly
- Welcoming dogs only
- Up to 23 kg per pet
Suitability/Accessibility
- Smoke-free property
- Note from host: We take this seriously, thanks
Services and conveniences
- Concierge services
- Iron/ironing board
- Meal delivery service
Location highlights
- In a rural location
- In the city centre
- Near a health/beauty spa
- Near a hospital
- Near an outlet shopping centre
- Near the bay
- Near the marina
- On a lake
- On the waterfront
Things to do
- Arcade/game room
- Bicycles
- Boat
- Foosball table
- Golf
- Heated pool
- Kayak
- Optional golf privileges
- Table tennis
- Tennis
- Water sports equipment
- Birdwatching nearby
- Casino nearby
- Cycling nearby
- Ecotours nearby
- Fishing nearby
- Golfing nearby
- Hiking/biking trails nearby
- Horseback riding nearby
- Hunting nearby
- Jet skiing nearby
- Motor boating nearby
- Sailing nearby
- Swimming nearby
- Water skiing nearby
- Water tubing nearby
- Winery tours nearby
Safety features
- Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
- Smoke detector (host has indicated there is a smoke detector on the property)
- First aid kit
- Fire extinguisher
- Deadbolt lock
General
- Bicycles
- Garden
- Unit size: 5,400 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 30
Check-out
Check-out before 10:30 AM
Contactless check-out
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Rules
Signed rental agreement required. See full house rules thanks.
Security: WiFi door lock for convenience for you & your guests. Exterior security cameras onsite; facing water and away from house
Pets: 1 dog. Not allowed on furniture or off-leash. Fully-refundable deposit req'd + $150 pet fee. Required to manage turnaround for the next guest
Pets
- Pets are welcome
- Only dogs are allowed
- Maximum 1 (weight limit: 50 lb per pet)
- Restrictions apply
- For more information, you can reach out to the property at the number on the booking confirmation Service animals are exempt from fees.
- Note from host: Must ask at booking. A fee plus deposit required.
Children and extra beds
- Children are welcome.
- Note from host: Love kids! House designed with a kids' floor!
Events
No events allowed
Only small, indoor parties
Smoking
Smoking is not permitted
We take this seriously, thanks
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
Note from host: Only small, indoor parties
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
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.
We should mention
- To make arrangements for your pet, contact the property directly using the information on your booking confirmation.
Property is also known as
House
Newer Luxury Waterfront Beach Pool Dock
Newer Luxury Waterfront - Beach, Pool & Dock Woolford