Entire home
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Family-friendly fun on the beach, with outdoor pool
Photo gallery for Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock





Reviews
9.8 out of 10
Exceptional
7 bedrooms5 bathroomsSleeps 18501.7 sq m
Popular amenities
Explore the area

Woolford, MD
- Place, Harriet Tubman Underground Railroad National Historical Park17 min drive
- Place, Choptank River Lighthouse22 min drive
- Place, Gerry Boyle Park at Great Marsh24 min drive
- Airport, Easton, MD (ESN-Easton - Newnam)48 min drive
Rooms & beds
7 bedrooms (sleeps 18)
3rd Floor Full's Bedroom
2 Double Beds
3rd Floor Twins Bedroom
+1
5 Single Beds
First Floor Den/Bdrm
1 Double Sofa Bed
Guest Room 2nd Floor
2 Single Beds
Guest Suite 2nd Floor
1 Queen Bed
Guest Suite 2nd Floor
1 Queen Bed
Master 2nd Floor
1 King Bed
5 bathrooms
3rd Floor Bath
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo
Ground Floor Bath
Soap · Towels provided · Bathtub or shower · Toilet · Shower only · Shampoo · Hair dryer
Guest Suite 1 Bath
Soap · Towels provided · Bathtub or shower · Toilet · Shower only · Shampoo · Hair dryer
Guest Suite 2 Bath
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer
Huge Master Bath
+1
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Jetted bathtub · Shampoo · Hair dryer
Spaces
Deck or patio
Porch or lanai
Kitchen
Office
Balcony
Separate dining area
Outdoor play area
Garden
Dining area
About this property
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
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly
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House Rules
Check in after 4:00 PM
Minimum age to rent: 30
Check out before 10:30 AM
Children
Children allowed: ages 0–17
Love kids! House designed with a kids' floor!
Events
No events allowed
Only small, indoor parties
Pets
Pets allowed: dogs less than 23 kg per pet (limit one pet total)
Must ask at booking. A fee plus deposit required.
Smoking
Smoking is not permitted
We take this seriously, thanks
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
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
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 the city centre and on the beach. The area's natural beauty can be seen at Blackwater National Wildlife Refuge and Bill Burton Fishing Pier State Park, while Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center are cultural highlights. Travelling with kids? Consider Richardson Maritime Museum and Ruark Boatworks. Jet skiing and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with hunting and horse riding nearby.

Woolford, MD
What's nearby
- Blackwater National Wildlife Refuge - 12 min drive - 11.4 km
- Harriet Tubman Underground Railroad National Historical Park - 17 min drive - 17.7 km
- Harriet Tubman Museum and Educational Center - 21 min drive - 23.0 km
- Choptank River Lighthouse - 22 min drive - 23.6 km
- Gerry Boyle Park at Great Marsh - 24 min drive - 24.7 km
Getting around
Restaurants
- Madison Bay - 8 min drive
- Woolford General Store - 8 min drive
- Boats & Hose - 16 min drive
- The Neck District Grill - 36 min drive
- Maryland Blue - 7 min drive
Frequently asked questions
About the host
Hosted by John
At first we rented out Saddle Beach a few weeks each summer to offset cost. Now we spend most of our time on the West Coast. Home is rented weekly in summer and weekends throughout the year. It's tough to be far away but we're still there often! Our full-time caretakers, Teri and Ken are wonderful and frankly, amazing. We also have a support group of great local vendors and contractors whose families have been the area for generations.
We love to help create vacation memories. Let us help you plan a great stay – enjy the property but you've got the potion to see the area as well. Go biking, hiking, sightseeing, crabbing, fish and boat around the area! Try the local restaurants and drive through the countryside – we have the areas only national wildlife refuge just 15 minutes away. Ask, ask ask! We want to help you plan! We have several repeat visitors each year. We are a real family and we have tremendous experience enabling family and similar vacations. We really do enjoy helping others make their own vacation memories on the Eastern Shore and the Chesapeake Region.
Why they chose this property
Size, beauty, location and amenities. Saddle Beach is the perfect vacation home for extended families and groups. It's gorgeous, with everything you need for best experience > on the property... or venture out to countless attractions, restaurants and recreation. Classic, private wraparound porches are a dream... The home was built with meticulous detail and an open floor plan, yet everyone says it feels warm and inviting. We built it for our family after a decade of planning.
The property is expansive and private and invites a week-long family event much like the family compounds of New England. It's a luxury property on the most elegant enclave of fine homes in the county, yet only ten minutes from the town of Cambridge, Maryland. The water is wide, calm and simply gorgeous! The Chesapeake Bay region is rural and water is everywhere.
What makes this property unique
You'll fall in love with the deep, stone wrap around porches, hand-cut, reclaimed walnut floors, and yet find it hard to stay inside with your own private pool, beach, dock, tidal pond and estate grounds.
Languages:
English, Spanish
Premier Host
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