Consider a stay at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted and take advantage of golfing on-site, a firepit and a garden. For some rest and relaxation, visit the sauna or hot tub, and indulge in a massage. Free in-room WiFi, with a speed of 500+ Mbps (good for 6+ people or 10+ devices), is available to all guests, along with a playground and an arcade/games room.
Reviews
9.89.8 out of 10
Exceptional
Entire home
7 bedrooms5 bathroomsSleeps 16502 sq m
Popular amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly
Add dates for prices
About this property
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 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
Property amenities
Beach
On the beach
Beach loungers
Beach towels
Pool/Spa
Heated pool
Hot tub
Massage
Outdoor pool
Private pool
Sauna
Internet
Available in the house: Free WiFi
Parking and transport
Car required
Parking on site
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Ice maker
Kitchen island
Lobster/crab pot
Microwave
Oven
Paper towels
Refrigerator
Spices
Toaster
Dining
Chef service
Dining table
Bedrooms
7 bedrooms
Bedsheets provided
Sofa bed
Bathroom
5 bathrooms
Bathtub
Bathtub or shower
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Fireplace
Living room
Separate dining area
Entertainment
Books
DVD player
Games
Smart TV with cable/satellite channels
Stereo
Outdoor areas
Balcony
Barbecue grill
Dock
Fenced yard
Firepit
Garden
Outdoor furniture
Laundry
Laundry facilities
Washing machine
Work spaces
Desk
Desk chair
Office
Comfort
Air conditioning
Heating
Pets
Pet friendly
Welcoming dogs only
Up to 23 kg per pet
Suitability/Accessibility
If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
In-room accessibility
No lift
Smoke-free property
Note from host: We take this seriously, thanks
Services and conveniences
Concierge services
Iron/ironing board
Meal delivery service
Location highlights
In a rural location
In the city centre
Near a health/beauty spa
Near a hospital
Near an outlet shopping centre
Near the bay
Near the marina
On a lake
On the waterfront
Things to do
Arcade/game room
Bicycles
Boat
Foosball table
Golf
Heated pool
Kayak
Optional golf privileges
Table tennis
Tennis
Water sports equipment
Birdwatching nearby
Casino nearby
Cycling nearby
Ecotours nearby
Fishing nearby
Golfing nearby
Hiking/biking trails nearby
Horseback riding nearby
Hunting nearby
Jet skiing nearby
Motor boating nearby
Sailing nearby
Swimming nearby
Water skiing nearby
Water tubing nearby
Winery tours nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
Signed rental agreement required. See full house rules thanks. Rates are set for 12 months. Ask about rates for stays that are longer than 12 months
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 peteposit req'd + $150 pet fee. Required to manage turnaround for the next guest
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total (up to 23 kg per pet)
Note from host: Must ask at booking. A fee plus deposit required.
Children and extra beds
Children are welcome
Note from host: Love kids! House designed with a kids' floor!
Events
No events allowed
Only small, indoor parties
Smoking
Smoking is not permitted
We take this seriously, thanks
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Note from host: Only small, indoor parties
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
We should mention
This property does not have any lifts
A car is required for transport to and from this property
About the area
Located in Woolford, this holiday home is in the city centre and on the beach. The area's natural beauty can be seen at Blackwater National Wildlife Refuge and Bill Burton Fishing Pier State Park, while Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center are cultural highlights. Travelling with kids? Consider Richardson Maritime Museum and Dorchester Arts Center. Jet skiing and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and horse riding nearby. Visit our Woolford travel guide
Harriet Tubman Underground Railroad National Historical Park
18 min drive - 18.4 km
Long Wharf Park
22 min drive - 23.6 km
Christ Rock Park
16 min drive - 17.2 km
Harriet Tubman Museum and Educational Center
22 min drive - 23.0 km
Getting around
Cambridge Station
22 min drive
Easton, MD (ESN-Easton - Newnam)
46 min drive
Restaurants
Boats & Hose
16 min drive
The Neck District Grill
36 min drive
Soft & Salty Seafood
45 min drive
The 948 Club
36 min drive
Millie's at Madison Bay
8 min drive
Frequently asked questions
Does Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
Is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted pet-friendly?
Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.
How much is parking at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?
On-site parking is available at the property.
What time is check-in at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?
Check-in begins at 4:00 PM.
What time is check-out at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?
Checkout is at 10:30 AM.
Where is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted located?
Located in Woolford, this beachfront holiday home is in the city centre and within 9 mi (15 km) of Blackwater National Wildlife Refuge, Christ Rock Park and Harriet Tubman Underground Railroad National Historical Park. Snows Turn Park and Bettys Island are also within 12 miles (20 km).
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Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted Reviews