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Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
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 ownerâs home is on 500 feet of private Chesapeake waterfront. Itâs 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. Itâs 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
We had an absolutely wonderful stay at this vacation rental! The property was amazing, and we had everything we needed for a relaxing getaway. The views of the bay were incredible, especially at sunrise and sunset.Communication with the owner was excellent from start to finish, and check-in/out was simple and stress-free. This was easily one of the best vacation rentals weâve stayed in, and we would absolutely return. Highly recommend to anyone looking for a relaxing spot with family and friends.
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 weâd absolutely stay there again!
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!
We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we even found a restaurant on our side of the bridge that could seat all 16 of us for seafood. If you need a beautiful house in an equally lovely Eastern Shore setting, you will be happy with this one.
We stayed at Saddle House during 2024 Ironman Maryland, with 2 Ironmans competing and lots of support traveling to stay. I was concerned choosing a house about 20 minutes from the start/finish but it was an amazing choice with great bike route access.
House is secluded and serene, amazing cleanliness, kitchen with everything you could ever need. Pictures are very accurate to the product you get. Jon was a great help finding things to do, house has incredible resources that support you during your stay like recommendations for everything you could think of. Kids loved the pool, everyone enjoyed the dock and many outdoor areas. Big enough house for everyone to have their own space and separate if needed.
Everyone that stayed with us loved the house and would come back again! Highly recommend to anyone looking for a getaway.
We enjoyed our stay a great deal. Jon is a great host, the house was comfortable and spacious, and the view of the night sky from the pier was spectacular.
A big, beautiful home with a well stocked kitchen, plenty of beds and space to gather!
This home boasts a wrap around porch, a built in pool, a pond and a 240' dock over the Chesapeake bay! From the dock, we fished, crabbed and caught the morning sunrise! The canoes, kayaks and bicycles provided were well used and appreciated. We are 8 adults and 12 children ranging from 1 year to 14 years old. A memorable, fun time was had by all. Communicating with Jon was always a pleasure. Thank you for sharing this amazing home.
Our June 2024 stay could not have been better!
Given the consistent stellar reviews, our extended Family traveled from Ohio to this wonderful Woolford waterfront home with already high expectations.
With that acknowledgment, we found the home, grounds and amenities simply perfect for our group ranging from 18-months to sixty-six years old!
The ground floor offered ample space for the kids to roam, play and watch TV. Most of our time was spent in the screened in porch, covered deck and pool area. The second and third floors offered great bedrooms plus a sitting area in which the adults could retreat for some quite relaxation!
The kitchen was extremely well-stocked with ample cooking utensils, a Keurig coffee maker and every size of pots and pans you could imagine!
The kids loved checking the crab traps, kicking the soccer ball in the yard and spending most of the day in the wonderful in-ground pool!
It is clear that Jon, the host, is dedicated to his guests positive experience, communicating consistently prior, during and after our stay. Most impressive, he actually called us from a Wedding he was attending upon our arrival Saturday to ensure our check-in went well!
In summary, I would highly recommend both this property and am confident you will receive "white glove" above and beyond service!
Wonderful house. Well stocked with supplies. Great open floor plan along with a couple separate spaces on the main floor. Our group had 7 adults and our eight grandchildren six and under. Pool has gated access which was a key feature with all our little ones. The owner provided much info regarding things to do in the area. The bedroom spaces worked out great with our mix. We really enjoyed the crab traps and the dock for fishing. It was mostly casting practice but the kids loved it. We enjoyed the fire pit in the evening. It is a relatively secluded location but within a couple miles of a country store and seafood market and about 10 miles from the town of Caimbridge with a Walmart for any shopping needs. I would highly recommend this for a family vacation like we had.
What a beautiful property! We did a quick couples getaway and couldnât have had a nicer weekend. The house is a beautiful, wraparound porch country home. Floorplan was really well designed and the decor was spot on. Looking forward to coming back next fall as well!
Spectacular! That sums up this gorgeous house and property. What an awesome spot with water all around. It felt like we were away from it all; but also close to the quaint town of Cambridge and beauty of Blackwater refuge. Jon was great to connect to and responsive to every question and need. We were 14 college friends now in our 60's and the house never felt crowded. There are so many spaces inside and out to gather. The kitchen was well stocked and the 2nd frig came in handy. Jon set us up with his crab guy and we started with a bushel of hard shells. The leftovers were made into the best crab cakes ever!! This place is extra special, we loved it! Thank you!!
We couldn't have asked for a better vacation. The house was large enough to accommodate all 11 of us and had enough space that we didn't feel on top of each other. The kids loved the 3rd floor zone. The house was well equipped with everything we needed for a fun time. The dock was perfect for catching fish, crabs, and even rays. The kayaks were great for early morning or late afternoon rides. The pool was huge and allowed us to cool off. The host was very responsive to our questions. We enjoyed it so much we've already booked the house for next year.
I was looking for a river vacation with my familyâŠsomething different than the Outer Banks we usually do. We ended the river and dock the most. The kids crabbed off it with the pots all week and caught 8 keepers.
We were able to keep the boat tied there for our early morning crabbing and fishing trips. It would have been better if we could have used the boat lift thereâŠwe had a pretty good storm and heavy rain that had us out there bailing out the boat in the midst of the heavy rain around 9:30 PM.
Caught 1 1/2 bushels of VERY nice hard crabs over the course of our stay that were so clean and delicious. Caught a few fish, but nothing big.
The pool was also a favorite.
Air conditioning was excellent and the tubs are all excellent. My bed was comfortable. The kitchen had everything you could need and the extras they provide was very nice: toilet paper, soap, p towels, etc.
We had a few glitches but our host was excellent in dealing with those issues very quickly.
Improvements would be to not have us clean and put away all the towels before we left. That was a problem.
We absolutely enjoyed our stay at Saddlebeach. The house and grounds were everything we were hoping for and more. There were 15 of us- 10 adults and 5 kids ranging in age from 2 to 10. There was plenty of bedroom and bathroom space. The children were especially happy to have the pool to jump into and the dock to fish from. The list of restaurants Jon provided was very useful - we found Old Salty's which we really liked.
We all had a wonderful time and are looking forward to coming back next summer
We ended up at Jon's property b/c our original VRBO had a last minute utility breakage that wasn't going to be able to be fixed by the time of our arrival. Being good neighbors (which says a lot), they worked with Jon to offer us a comparable stay on this property instead. The communication & amount of helpful detail on the area that I got from Jon FAR exceeded anything I've had from other rentals anywhere, and his outreach was not only super detailed, but personable & friendly, by text, email and by phone. If you're wondering what you're going to "do" in the area, go ahead & rent & when Jon sends you his list of things in the area you won't wonder any more. I wish this host had properties elsewhere in the US too! The property itself is GORGEOUS - I hope occasion will bring our group back again at another time to explore other seasons. Sufficiently isolated to feel free & easy, yet close enough to town for meals out every night if we wanted (and a big ol kitchen if we didn't), this place really has it all, and every person in my group was pleased. It's a bit odd for paper products to not be already available, but Walmart is easy, and the property is a bit further from BWI than we would have liked, but you don't get gorgeous countryside right near an international airport. Totally worth it :) It was March when our group travelled, and I bet the lakefront & surrounding areas are even more beautiful in the summer & fall. Definitely recommended, would absolutely rent again.
Saddle Beach was roomy, well equipped and very comfortable for our Family Holiday getaway! We enjoyed card & board games by the indoor gas fireplace, and talks around the outdoor fire pit. Cornhole games, long walks/runs, and trips to the wildlife refuge and Tubman Museum filled out the week. Good times for all!