Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
4.9
Outstanding(70 Reviews)House in Chesapeake Bay, NC
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
Includes essentialsGarden, Pool, Pets allowed and more
About this house rental
** Pool open April 1 - Book 3 nights get the 4th FREE through April **
Families and groups LOVE our 7 Bedroom, 5 Bath luxury property
5+ acres, 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
Families and groups LOVE our 7 Bedroom, 5 Bath luxury property
5+ acres, 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
Amenities
Pool
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
Hot tub or spa
TV
Garden
Family friendly
Map of Chesapeake Bay, NC
Reviews
4.9
Outstanding(70 Reviews)4.9
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.
4.9
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.
4.9
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.
4.9
What a beautiful property! We did a quick couples getaway and couldn’t 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!
4.9
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!!
4.9
great property!
4.9
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.
4.9
I was looking for a river vacation with my family…something 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 there…we 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.
4.9
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
4.9
Great for families, and we have a big one. 8 adults and 7 kids (2 to 11 year olds) and plenty of room for all.
4.9
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.
4.9
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!
4.9
Wonderful weekend at this delightful property on the Eastern Shore. Quiet. Peaceful. Just perfect.
4.9
We spent Thanksgiving at this property, and we had a ball! Family members from Texas and California flew in and family from DC drove over. The kitchen was well stocked for roasting a turkey and making all the sides, including two kinds of stuffing. Thank goodness for double ovens! Everyone slept comfortably, and there was plenty of room to spread out. We did s'mores over the fire pit, took long walks, rode bikes and sat out on the dock watching the water. It couldn't have been any better. The owners were so helpful with suggestions of where to go. The seafood from the Kool Ice & Seafood was outstanding. And Emily's Produce was so amazing, we stopped by pretty much every day. The den area was so big with comfortable seating, and we sat around the fireplace and watched the Thanksgiving Day parade, played games, puzzles, visited, etc. We would love to come back. It's just a beautiful area of the United States.
4.9
We had 7 families gather for a weekend away and Saddle Beach was perfect! Large family room inside where everyone could comfortably gather and excellent options outside for activities. We only wish the weather had been better so we could have spent MORE time outside!
4.9
Jon is a super attentive host and his place is one of the nicest properties in the Woolford/Cambridge area. Kids caught crabs off the dock and enjoyed the canoes and kayaks Jon supplied. House had more than enough space for the adults and kids to all relax and eat together.
4.9
The house provided great accommodations for our large, extended family, and the pool and third floor were great for the grandchildren.
It was a very hot week, so we understand the challenges for the AC, but we couldn’t get the main floor or the third floor cool.
4.9
A very nice property. We made great use of the pool, kayaks, bikes & fire pit. There was ample space for everyone. We had a few issues, but Jon was communicative and sent someone out to resolve them.
4.9
We stayed at Jonathan's home for our multigenerational family reunion and Easter gathering. The home was incredible, with more than enough space to spread out for the adults and kids, and it had all the supplies and amenities we needed for family meals, daytime activities (from swimming in the pool to kayaking), and nightttime smores by the water. Jonathan was an incredible host. He was highly responsive, transparent, and worked with us to accomodate our particular needs. We will definitely stay here again in the future. Thank you for making this such a memorable experience!
4.9
Our family had a wonderful week in Woolford, MD. The house was just "as advertised" with room for games, lively conversations, and quiet reading. The dock was perfect for fishing and all our young people caught [and threw back] several fish. The kayaks and bikes were put to good use by everyone. Jon was friendly and answered our questions promptly. The house was well equipped with towels and kitchen supplies. Thank you for sharing your lovely home.
4.9
Large house that easily accommodated the 14 people we had. The pool made the trip for the kids. Slightly difficult getting in and out of our boat with the dock high above the waterline, and no spring line pilings, but we managed with a Bahama style anchor line. I'm just use to floating docks. Quiet is an understatement. Not even much boat traffic. Great place. Not disappointed.
Only suggestion: Move the WalMart closer to the house.
4.9
Saddle Beach was the perfect weekend home for our family gathering. The setting on the river is gorgeous. We enjoyed the outdoor spaces like the docks and pool and the interior common areas are also attractive and spacious. Jon was very helpful and accommodating leading up to our stay. Thank you!
4.9
Just a wonderful property, with everything we could have asked for to help celebrate a wonderful occasion for our Mom. Both the actual accommodations, rooms, beds, baths, amenities, as well as the layout of the property were just great, whether we wanted to be together to celebrate, or spend quiet time reading a book, fishing, or just taking in the beautiful views! Several great gathering places inside and out, and we used them all! Would definitely recommend and hope to visit again!
4.9
My friends and I had an amazing stay at Jon’s property this winter. The accommodations were immaculate and Jon was very easy to get in touch with, and provide great recommendations for the area.
4.9
Our family had lots of room to spread out, to sit down and eat together, and to be active outdoors! Something for everyone…fishing, kayaking, walking, football and cornhole…or enjoying the quiet with a book, some knitting, or a nap! Great house in an amazing spot…and easy to get to civilization for necessities and SEAFOOD!
4.9
We had our family Christmas over Thanksgiving break at this home. We had a total of 12 people ranging in age from 11 to 75. The location is great. It was too cold to enjoy the water but the kayaks were available. There were enough bikes for those who wanted to use them. We enjoyed the nearby Blackwater NWR and the Harriet Tubman Underground Railroad Historical Park. The house itself is well maintained and we had no problems. The owner called us on Thanksgiving to see how we were doing and to wish us a happy holiday. All in all, a great place to stay.
4.9
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 !!
4.9
This house / property was excellent for our annual family get-together...especially after the last isolated Covid year. The house provided us with multiple dining areas (for eatting and games / puzzles) and also bedroom choices. The teens especially liked their third floor bedrooms / entertainment area. We all made use of the outside amenities of screened porch, side deck (family photos) , pool, fire pit and kayaks.
There were some minor maintenance issues which the owner addressed.
We found the following visitor areas to be close and interesting : the newer Harriet Tubman museum / video, Blackwater National Refuge, Chesapeake Ghost Walk and the St. Michael's Skipjack sail. (The last two we reserved for our private family experience).
4.9
Easy check in and out. Enjoyed the use of the kayaks. Pool very refreshing. Crabbing was great.
4.9
We had a wonderful stay including boating, kayaking, swimming, fishing, campfires and crabs! The house was perfect for our group and the owner was very accommodating.
4.9
We chose this place to stay during a duck hunting trip because it was centrally located for all the spots where we would be hunting. The house was a perfect fit. The location was just right. We were able to spread out in the house and the views were amazing. Everything was exactly as advertised. Would highly recommend and we will be going back next year.
4.9
We made a last minute decision to spend a few days away from the city (DC) and in seclusion somewhere along the Chesapeake and this house met all our criteria. Beautiful, spacious (we were 5 people), well kept, nicely furnished (interesting pieces and decor from France) with all the amenities you'd need. It seemed we were the only people around, other than the locals, which was nice. The instructions and suggestions by the owner were spot on and helpful. Definitely will look to returning for more than just a few days.
4.9
We really enjoyed this peaceful retreat. Great for family gatherings with lots of space and great outdoor options. Even though it was cold and windy we went canoeing and our kids played on the little beach. We would love to return in warmer weather.
4.9
Our annual friends getaway this year was fabulous! The location of this beautiful home right on the water, the pier, the view, fire pit and kayaks all made our stay very enjoyable. See you next year!
4.9
We had a great long weekend at this property. The house was super clean, spacious, and comfortable. It offered plenty of varied options to sleep, sit, and relax. Kitchen was well equipped with modern appliances and stocked with utensils, cooking supplies, etc.Owner was very responsive and flexible and provided some very detailed tips for the local area, many of which we took advantage of. He even checked in on us via text message during the stay, which we've never experienced before with vacation rentals.Our kids loved the beach and found plenty of interesting shells. We tried our hand at crabbing and came up empty but the kids still enjoyed it. We took out the kayaks (which were in great condition) one afternoon for their first kayak trip and that was really neat. Area around the property is very quiet and peaceful. Sitting on the dock to read a book was really nice.The only negative point about our trip was the mosquitos. They were intense. While first unpacking the car (prior to applying bug spray), I got at least ten bites. No exaggeration. Bug spray definitely helped but if you missed a spot, they found it. Even with bug spray, they were constantly bouncing off you. As a result, we weren't able to spend time on the wooden platform by the pond. They thinned out considerably by the firepit and beach and disappeared completely on the dock.Also, just note that digital entertainment options are limited. Internet (as noted by the owner) is too slow for streaming. There is satellite TV but limited channels. Luckily for us, there were at least several children-focused channels. There's a handful of DVDs around and two DVD players in the house. That was all fine for us. We caught up on reading and other activities, but some families might want to bring media and maybe even additional players.That all said, it was a great place to spend a few days to relax and see the surrounding area and we'd definitely recommend it for other renters!
4.9
Blissful week on the Chesapeake Bay
FAQs
How much does this house cost compared to others in Chesapeake Bay?
The average price for a rental in Chesapeake Bay is $266 per night. This rental is $709 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
Yes, a swimming pool is available for use at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock. Enjoy the water!
Is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock 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, Pets, Dock?
We found 14 amenities for this rental. This includes pool, air conditioner, pets allowed, kitchen or kitchenette, and internet / wifi.
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