Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted

Top rated by guests
Our home blends into towering pines, lawns & hundreds of feet of waterfront
Kitchen & dining areas open to living rooms
Kitchen
Gorgeous pool just off the kitchen /porch
Exterior
review stars
9.8Outstanding
(76 Ratings)
Exceptional property for family vacations, providing a beautiful setting, well-equipped amenities, and various activities like fishing, kayaking, and swimming. Highly recommended.
From real guest reviews summarized by AI
Don't miss out! Price and availability may change
9.8 / 10
Outstanding(76 Ratings)

House in Maryland

18 guests · 7 bedrooms · 5 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this house rental

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 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.
** - We've been renting our 5-Star property for 20 years and always share phone and email (required) to ensure we can be the very best host and so we can reach each other during your stay if needed! In addition, email allows us to send our welcome information which includes photos and links that can't be sent through the platform!
** - Outdoor (only) security cameras face the driveway and water

Amenities at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted

Non-smoking
Pets allowed

Map of Maryland


Ratings and reviews

9.8 / 10
Outstanding(76 Ratings)
review starsSummary of reviews
Exceptional property for family vacations, providing a beautiful setting, well-equipped amenities, and various activities like fishing, kayaking, and swimming. Highly recommended.
From real guest reviews summarized by AI
10 / 10Outstanding·Dec 2025
The home is in a stunning location, and was perfect for our family gathering over the Thanksgiving holiday. Everything you need for a relaxing, enjoyable getaway is provided in this home, and we’d absolutely stay there again!
10 / 10Outstanding·Aug 2025
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.
10 / 10Outstanding·Aug 2025
As beautiful as the photos appear, they do NOT do this place justice! Just a beautiful place, incredibly peaceful, well-appointed and equipped for families, groups, or any type of rental. Loved our time here!
5 / 10·Nov 2021
I was at Jonathan’s place for a yoga /meditation retreat with some colleagues and it was absolutely amazing! The water views and private dock were beautiful! There is also a pond with a deck and some chairs and a little beach. Lots of unique spaces to hang out outdoors. The house itself is very large and open and well furnished. The kitchen is well stocked and open to the living room and dining room. The bedrooms are all a nice size and most have private bathrooms inside the rooms. Communication with Jonathan was wonderful. He always answered promptly and was available for questions. He even let us check in early and check out late to accommodate our retreat schedule . The neighborhood is also very quiet and private. We rode the bikes provided down the private road which is a couple of miles long. Lovely all around and I would highly recommend this house !!

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?

We found 2 amenities for this rental. This includes non-smoking, and pets allowed.