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

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

A two-story house with a red roof, a covered porch, and a swimming pool. -  Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted (Woolford)
A sandy beach with a wooden pier extending into calm water. -  Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted (Woolford)
A swimming pool with lounge chairs and a house in the background. -  Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted (Woolford)
A dining area with a wooden table and chairs, a floral armchair, and a view through a glass door. -  Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted (Woolford)
A wooden deck with chairs and a table by a calm lake, surrounded by trees. -  Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted (Woolford)
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

9.8 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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles
  • Garden
  • Unit size: 5,400 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 30

Check-out

Check-out before 10:30 AM
Contactless check-out

Special check-in instructions

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
View more Holiday homes in Woolford
Map
Woolford, MD

What's nearby

  • A wooden boardwalk extending into a grassy field.
    Blackwater National Wildlife Refuge
    7 min drive - 6.5 km
  • A modern building with large glass windows, a metal roof, and a small tree in the foreground.
    Harriet Tubman Underground Railroad National Historical Park
    18 min drive - 18.4 km
  • A marina with numerous sailboats docked at wooden piers.
    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