Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Select date
-
Select date
1 night
All properties in Dorchester County

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

Dorchester County, Maryland, 21677
Show on map
Complete address will show after booking
We Price Match
hotel overview picture
Amenities
Golf course
Pool
Horse riding
Hiking
Sauna
Tennis court
Table tennis room
Wi-Fi in public areas
All amenities
Property Description
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 waterAbout pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).Must ask at booking. A fee plus deposit required..About checkOut:Check out before 10:30 AM.About children:Children allowed: ages 0-17.Love kids! House designed with a kids' floor!.About customRules:Signed rental agreement required. See full house rules thanks..Security: WiFi door lock for convenience for you & your guests. Exterior security cameras onsite; facing water and away from house,Pets: 1 dog. Not allowed on furniture or off-leash. Fully-refundable deposit req'd + $150 pet fee. Required to manage turnaround for the next guest.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.We take this seriously, thanks.About minBookingAge:Minimum age to rent: 30.About events:No events allowed.Only small, indoor parties.
Show more
9.8/10
Outstanding
Cleanliness9.8
Amenities9.8
Location9.8
Service9.8
All 11 reviews
Surroundings
Airport: Easton Airport
(49.6 km)
Landmarks: Old Trinity Church
(5.4 km)
View on map

Overview

Rooms

Guest Reviews

Services & Amenities

Policies

Host

7

7 Bedrooms Private Vacation Home

7 bedrooms: 7 single beds 1 sofa bed 2 queen beds 2 double beds and 1 king bed
Free Wi-Fi
Non-smoking
Air conditioning
Refrigerator
TV
Towels
Room Details
Check Availability

Guest Reviews

9.8/10
Outstanding
11 reviews
Verified Reviews
  • Cleanliness9.8
  • Amenities9.8
  • Location9.8
  • Service9.8
Average for similar properties in Dorchester County

Book now and leave a review after your stay to earn up to 120 Trip Coins (approx. PHP 70.81). Trip Coins can be used to save instantly on room rates.

Most Mentioned
L‍i‍n‍d‍a‍ ‍S‍.
August 25, 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.
c‍a‍t‍h‍y‍ ‍L‍.
July 17, 2024
Vacation paradise 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.
W‍i‍l‍l‍i‍a‍m‍ ‍P‍.
June 26, 2024
Exceeded Our Expectations! 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!
C‍h‍r‍i‍s‍t‍i‍n‍e‍ ‍F‍.
December 5, 2023
Perfect Weekend Getaway 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!
R‍o‍b‍i‍n‍ ‍Z‍.
October 26, 2023
Waterfront wonderland! 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!!
W‍i‍l‍l‍i‍a‍m‍ ‍P‍.
July 28, 2023
Saddlebeach 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
J‍o‍a‍n‍n‍e‍ ‍A‍.
July 31, 2023
Fun at Saddle Beach 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.
C‍a‍r‍o‍l‍ ‍N‍.
April 11, 2023
Sunshine, dolphins and campfire, oh my! 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.
M‍a‍r‍k‍ ‍S‍.
January 17, 2023
Eastern Shore Respite Wonderful weekend at this delightful property on the Eastern Shore. Quiet. Peaceful. Just perfect.

Services & Amenities

Table tennis room
More Amenities
Internet
Pool
Front desk services
Public areas
Health & wellness
Activities
Facilities for children

Property Policies

Check-in and Check-out Times
Check-in: after 16:00
Check-out: Before 10:30
Child policies
Children of all ages are welcome at this property.
Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.

Cribs and Extra Beds
Please contact the hotel for details about crib and extra bed policies.

Age Requirements
The main guest checking in must be at least 30 years old

Property host

John
Speaks: English, Spanish

About this property

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 waterAbout pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).Must ask at booking. A fee plus deposit required..About checkOut:Check out before 10:30 AM.About children:Children allowed: ages 0-17.Love kids! House designed with a kids' floor!.About customRules:Signed rental agreement required. See full house rules thanks..Security: WiFi door lock for convenience for you & your guests. Exterior security cameras onsite; facing water and away from house,Pets: 1 dog. Not allowed on furniture or off-leash. Fully-refundable deposit req'd + $150 pet fee. Required to manage turnaround for the next guest.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.We take this seriously, thanks.About minBookingAge:Minimum age to rent: 30.About events:No events allowed.Only small, indoor parties.
Show Full Description

Frequently Asked Questions

What’s the cancellation policy at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock?

The cancellation policy at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock depends on your room type and booking terms.

What are the check-in and check-out times at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock?

Check-in at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock starts from 16:00, and the standard check-out time is by 10:30.

How do I get to Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock from the nearest airport?

The nearest airport is Easton Airport, located about about 42 mins from hotel by car (49.6 km) away.

About This Property

Nearest AirportEaston
Distance to Airport49.56KM
Hotel Star Rating4