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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Newer Luxury Waterfront - Beach, Pool & Dock

Bedrooms 6
Space 5,400 sq. ft.
Property type house
Minimum Stay 2 - 7 nights


About the property

6/7BR 5BA Sleeps 18+ - Massive porches - mile-wide views - sandy beach

Family retreat perfection!

(We have two, literally identical homes! - the other is pet friendly)

This fabulous, newer waterfront owner’s home is on 500 feet of private Chesapeake waterfront, 10 mins from the lovely town of Cambridge, & close to St Michaels, Easton and Oxford.

Over 5 acres of secluded estate. A grand vacation home with wraparound 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.

Six/Seven bedrooms. 5 bathrooms and it’s all spread out on 3 beautiful floors.

'Saddle Beach' is on Dorchester County's exclusive McKeil Point just off the Chesapeake Bay. The property has a mile-wide view and a 200' dock. The home is exceptionally furnished, has 4200sf of living area with another 1200sf of open and screened porches.

6 bedrooms, a den with sofa-bed and full bath. 5 baths, a large eat-in kitchen with 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, hand-cut wide-plank walnut floors. A tidal pond is just off the living room.

The Property:

A perfect Family Retreat!

Gorgeous wraparound 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 loblolly 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 & lounge chair 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.

The Area:

A local country store, restaurant and boat ramp is 3 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 colder days and nights. 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 from 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 nine and 19 miles away.

More Details

Member since: 2005
Speaks: english, spanish
Response time:
Within a few hours
Response rate:
Calendar last updated:
March 20, 2018

About 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. Homes are rented weekly in summer and weekends throughout the year. We are there often ourselves. Our caretakers, Michele and Jamie are like family and wonderful. We have a support group of great local vendors and contractors whose families have been the area for generations.

For years we have listed our home. We don’t break even on these, but they work for our needs and the rentals help us keep them in the family.

We love to enable vacations. Have a great stay – see the area as well as enjoy our property. Go crabbing, fish and boat around the area! Try the local restaurants and drive through the countryside – there’s no place like it in the country. Ask, ask ask! We want to help you plan! We have several repeat visitors each year.

We are real people, a real family and we have tremendous experience enabling family and similar vacations. Since we can rarely take our family there now, we enjoy helping others make their own vacation memories on the Eastern Shore and the Chesapeake.

John purchased this house in 2005

Why John chose Woolford

This home was built with meticulous detail and an open floorplan, yet still feels warm and inviting to it's guests - 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.

The water is wide, calm and simply gorgeous!

Guestbook comments from the owner

Our family traveled from Indiana to Maryland this past July for a week of just being truly was the best week ever.

We had fourteen people, 6 of the fourteen were children ranging from ages 2-14... My children are older and it is so much fun to see them at different stages in life, I think the best stage is when they are adults, and to see them with their own children...we went boating, crabbing, swimming, played games and sat around the campfire.

The house was perfect, plenty of room, everything was in order when we arrived, and if we had any questions during our stay we texted Jon and he was very prompt with an answer. We also took one day and traveled to Washington D.C. making memories with our children and grandkids is the most important thing to our family, and we really made some great ones.... looking forward to doing this again..
Jul 2017
  • 1 of 1


Woolford House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 5400 sq. ft.
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:30 AM
  • Max. occupancy: 20 ...
  • Min. age of primary renter: 30 ...
  • Children welcome ...
  • Parties/events not allowed ...
  • Pets not allowed ...
  • Non smoking only ...
Location Type:
  • Beach ...
  • Beach View ...
  • Beachfront ...
  • Downtown ...
  • Rural ...
  • Water View ...
  • Waterfront ...
  • Waterfront ...
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Activities Guide
  • Air Conditioning ...
  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Clothes Dryer ...
  • Fireplace ...
  • Heating ...
  • Internet
  • Laundry Soap
  • Linens Provided ...
  • Living Room ...
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Mosquito Magnet
  • Parking ...
  • Parking Off Street
  • Parking On Street
  • Shampoo
  • Telephone ...
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine ...
  • 4 Ring Stove
  • Blender
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Grill
  • Ice Maker
  • Kitchen ...
  • Lobster Pot
  • Microwave ...
  • Oven ...
  • Refrigerator ...
  • Stove ...
  • Stove
  • Toaster ...
  • Dining Area
  • seating for 12 people
  • 5 Bathrooms
  • Master - toilet , tub , shower , jetted tub , Jacuzzi tub and separate, huge shower w/ steam room
    Guest Suite 1 - toilet , shower
    Guest Suite 2 - toilet , combination tub/shower
    3rd Floor Suite - toilet , tub
    Ground FLoor - toilet , shower
  • All baths boast tile floors or granite throughout.
  • 6 Bedrooms, Sleeps 20
  • Master 2nd Floor - 1 king , Attached bath with tub and steam shower
    Guest Suite 2nd Floor - 1 queen , Attached bath with shower
    Guest Suite 2nd Floor - 1 queen , Jack/Jill bath
    Guest Room 2nd Floor - 2 double , portacrib avail. Hall bath
    3rd Floor Bedroom Fulls - 2 double , Two large, Full beds. Hall bath
    3rd Floor Bedroom - 5 twin/ single , Four twins and a trundle. Hall bath
    3rd Floor Rec area - 1 sleep sofa /futon , Hall bath
    Den/Bedroom 1st Floor - 1 sleep sofa /futon , Office has a full/double sofabed & private bath with shower
  • Five of the bedrooms are bed/bath suites One bath has a hallway door for the 6th bedroom All bedrooms are luxuriously appointed.
  • Books
  • Books for Adults
  • Books for Kids
  • CD Player
  • DVD Player
  • Radio
  • Satellite / Cable ...
  • Stereo
  • Television
  • Toys
  • VCR
  • Balcony
  • Barbecue
  • Beach Towels
  • Bicycles
  • Boat ...
  • Boat Dock
  • Boat with Paddles
  • Canoe
  • Deck / Patio ...
  • Golf ...
  • Kayak / Canoe
  • Lawn / Garden
  • Outdoor Grill ...
  • Outdoor Grill Gas
  • Patio
  • Porch / Veranda ...
  • Sand Box
  • Screen Porch / Veranda
  • Tennis ...
  • Terrace
  • Unscreened Porch / Veranda
  • Walkway to Water
  • Water Sports Gear ...
  • Wood Deck
  • 4 bicycles
  • 6 garden chairs
  • 3 beach chairs
  • wheelchair inaccessible ...
Pool / Spa:
  • Jacuzzi
  • Outdoor Pool
  • Private Pool ...
  • Sauna ...
  • Spa Whirlpool
  • Steam Shower
  • Whirlpool
  • Whirlpool
Onsite Services:
  • Car Optional
  • Massage
  • autumn foliage
  • bay/sound
  • churches
  • cinemas
  • coin laundry
  • festivals
  • forests
  • library
  • marina
  • museums
  • playground
  • pond
  • recreation center
  • restaurants
  • synagogues
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • horseback riding
  • outlet shopping
  • paddle boating
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • equestrian events
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • hunting
  • hunting big game
  • hunting small game
  • jet skiing
  • pier fishing
  • roller blading
  • sailing
  • sound/bay fishing
  • surf fishing
  • swimming
  • tennis
  • water skiing
  • water tubing
Canoe and Kayak provided Bicycles provided Motorized skiff available for rent from nearby marina Dock accommodates boats up to 40'. 3' MLW at dock.


Excellent! 4.6/5 -
(15 traveler reviews)

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Newer Luxury Waterfront - Beach, Pool & Dock
average rating of 4.6 based on 16 reviews

Beautiful home in a stunning setting!

  • 5 of 5

Our group of three families had a wonderful weekend stay at this lovely home. The home is spacious, bright, clean, and beautifully furnished. The water views are gorgeous- especially at sunrise and sunset. The owners are very helpful and responsive to questions about the house and the surrounding area. We hope to return soon!

  • Submitted: Dec 19, 2017
  • Stayed: December 2017
  • Source: HomeAway
Owner's Response: This guest was lovely! We book full in the summer, yet have so many families and couples stay throughout the year. The town and surrounding areas have so much to offer from recreation to dining the sightseeing, but the property makes the trip… We’re glad to have helped make a special weekend for these wonderful folks and look forward to having them back!.
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0 0

Beautiful home that met all our expectations.

  • 4 of 5

The property was one of the few that met our requirements for our 18 member family ranging in age from 14 to 92. The pool was a necessity and got used constantly with the 90-100 degree temps. There was a free boat ramp a few miles away and it was only a 4 mile boat ride to the center of the Chesapeake Bay where the crabbing and striper fishing was excellent.

The dock also offered fair crabbing and good boat docking.

The property is somewhat secluded on a narrow peninsula that extends into the Little Chop Tank river, but restaurants, country store, and a wildlife sanctuary are close by. The water in the river was relatively calm allowing perfect canoeing , but swimming was not possible due to the large numbers of jelly fish in the river.

Outside maintenance could be improved with replacement of several loose boards on the boardwalks.

  • Submitted: Jul 24, 2017
  • Stayed: July 2017
  • Source: HomeAway
Owner's Response: Such a great guest! Loved having their family! We do appreciate the suggestions and the boards were addressed the day they left. Sea Nettles are in the Chesapeake Bay and rarely dense up as far north as we are. But we had little rain up to that week and the higher salinity contributes to it. With this week's rains they are all but gone. One of the few things we can't control :) Can't wait to have their family back!
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2 0

Great getaway

  • 5 of 5

We are a mens church group which schedules a getaway once a year. In the past we have rented Jon's other property, Hudson Shores and found it really meets our needs. Last year Jon suggested that we try Saddle Beach. Listen to this man. He is a great host who knows his properties. Great location, great house, great views.

The men made it clear that we will be returning to Saddle Beach this year. Between fishing / crabbing, kayaking, swimming in the pool, or just enjoying the house they were able to relax and fellowship.

Town is close enough if you run out of something, (these men can eat when they relax), but why leave this property.

  • Submitted: Mar 16, 2017
  • Stayed: September 2016
  • Source: HomeAway
Owner's Response: Most of our guests are family groups, but this is a group of gentlemen that of been coming for years. There's no better compliment than to have repeat guests year after year and we're grateful. And they are gentlemen in every sense.
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2 0

Wonderful weekend retreat!

  • 5 of 5

We had an amazing stay - Jon was super helpful and responsive prior to and during our stay! The home is absolutely beautiful and the setting is idyllic - we loved having our own beach! The bedrooms were super cute and comfortable and the main room was plenty large enough for our group to relax and watch movies. The house is very well equipped - we had more than enough of what we needed in the kitchen to feed 11 of us. Would definitely return and absolutely would recommend the property others!

  • Submitted: Feb 18, 2017
  • Stayed: January 2017
  • Source: HomeAway
Owner's Response: What a lovely guest and group!! It really make us happy to be a part of family and group getaways and is such a pleasure to hear they had an excellent stay. We hope to have them back soon as we do so may others.
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4 0

Lovely family reunion home with pool and river

  • 5 of 5

Our family gathering was everything we hoped because of this vacation home. The house met the needs for the 13 of us, from 4 to 67 years old. We especially loved the different seating areas, and I think the kids turned into prunes because they were in the pool so much. We played games, had sing-alongs, went biking, kayaking and explored towns and restaurants.

We truly appreciate all the thought that went into this home! Jon was a joy to work with: so helpful and raesponsive.

  • Submitted: Jul 12, 2016
  • Stayed: July 2016
  • Source: HomeAway
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3 0

Excellent place for multiple families!

  • 5 of 5

Crabbing, Swimming, Biking, Kayaking, Relaxing, Etc. Kids loved the crabbing part. Not many places you can do all those sort of things. Best rental house we've ever had. 3 families with a total of 12 people, had a wonderful time. We never felt we were 'on top' of each other. Everyone had enough space in and out of the modern home. A true Chesapeake experience. We look forward in returning.

  • Submitted: Oct 12, 2009
  • Stayed: August 2009
  • Source: HomeAway
Owner's Response: Lovely guests; thanks for such a nice review. Providing a place for extended families to enjoy their coveted, once-a-year reunion is one of the great pleasures we get from our home.
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7 0


Nearest Airport
80 Miles
Nearest Barpub
2 Miles
Madison Bay
Nearest Golf
10 Miles
Hyatt Chesapeake Bay Resport
Nearest Train
80 Miles
Nearest Motorway
8 Miles
Route 50 and Route 16
Nearest Restaurant
2 Miles
Nearest Beach
30 Metres
On Property
Car: recommended

Waterfront luxury in a new, private compound for you, your family and guests. Just 10 minutes from Cambridge on a river just off the Chesapeake bay. Swimming, exploring, sunbathing, private pool, boating, crabbing, fishing and sightseeing. Incredible biking. The Cambridge, Easton, St. Michaels Oxford area has too many attractions to list. All the amenities you could want are close by. There is a pristine acre-sized pond next to the house that often provides rest to swans, ducks and geese. Wildlife abounds; you may find yourself crabbing and fishing all day. Boar use included.

The neighborhood consists of a mile-long peninsula of the finest homes, stretching far into The Little Choptank River. The quiet street invites scenic bike rides or long walks to watch the sunsets. The Chesapeake Bay with it's fishing, cruising and endless sunsets is a stone's throw away.

The town of Cambridge is less than ten mins away, & it’s not much further to visit Oxford, Easton, or S

Golf: The town of Cambridge is very close with choice restaurants (including some fun places on the water), a beautiful section of historic homes and interesting shops. The Hyatt Chesapeake has much for the visitor including a great spa, the golf course, marina, three restaurants, and night-time movies with food service at the indoor Wintergarden pool for all. There are two restaurants on the water just moments away, and another dozen choices just minutes further.

In the summer, there are more than ample cultural, historical, culinary, architectural, and nature festivals shows and concerts. Drive beyond 30 minutes and visit Crisfield Island, Ocean City, Maryland, or the Delaware Shore for a day at the ocean, or see the famous wild ponies of Chincoteague Island.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $500
Cleaning $299
Tax Rate 11.0%

- Short stays available for non-Summer weekends
- * Major Holidays such as Thanksgiving, Winter holidays and New Years, along with events (i.e. race) rates are higher and may require a minimum stay.
- Credit Card payment available - 3% fee applies
Each Guest over 18 guests incurs a charge of $25 per night
** If you book through Homeaway we still require a signed agreement, as we have done for ten years for our mutual protection.
Rates subject to change without notice

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.