Entire home

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

Family-friendly beachfront vacation home with outdoor pool

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

Outdoor pool, a heated pool
Exterior
Outdoor dining
Fridge, microwave, oven, stovetop
On the beach, sun loungers, beach towels

Reviews

9.8 out of 10
Exceptional

Entire home

7 bedrooms5 bathroomsSleeps 185400 sq ft

Popular amenities

  • Beach view
  • Barbecue grill
  • Pool
  • Pet friendly
  • Parking available

Explore the area

View in a map
Woolford, MD
  • Harriet Tubman Museum and Educational Center
    ‪28 min drive‬
  • Choptank River Lighthouse
    ‪29 min drive‬
  • Long Wharf Park
    ‪29 min drive‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪58 min drive‬

Room options

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About the neighborhood

Woolford

On the beach.At this Woolford vacation home, you'll be within 6 miles (10 km) of Blackwater National Wildlife Refuge and 9 miles (15 km) of Harriet Tubman Underground Railroad National Historical Park. Also within 9 miles (15 km) are Harriet Tubman State Park Visitors Center and Christ Rock Park.

What's nearby

  • Blackwater National Wildlife Refuge - 16 min drive - 7.1 miles
  • Harriet Tubman Museum and Educational Center - 28 min drive - 14.3 miles
  • Choptank River Lighthouse - 29 min drive - 14.7 miles
  • Long Wharf Park - 29 min drive - 14.7 miles
  • Gerry Boyle Park at Great Marsh - 31 min drive - 15.3 miles

Getting around

  • Cambridge Station - 22 min drive
  • Easton, MD (ESN-Easton - Newnam) - 46 min drive

Restaurants

  • ‪Madison Bay - ‬8 min drive
  • ‪Woolford General Store - ‬8 min drive
  • ‪Boats & Hose - ‬16 min drive
  • ‪The Neck District Grill - ‬36 min drive
  • ‪Madison Bay Restaurant - ‬7 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

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 water

Similar properties

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 transportation

  • Car required
  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • 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
  • One pet total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed
  • 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 center
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • 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

Policies

Check-in

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

Check-out

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

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Rules

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

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 (weight limit: 50 lbs per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees
  • 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

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
Onsite parties or group events are strictly prohibited
Note from host: Only small, indoor parties
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. Note from host: Only small, indoor parties For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

Property is also known as

House
Newer Luxury Waterfront Beach Pool Dock
Newer Luxury Waterfront - Beach, Pool & Dock Woolford

Frequently asked questions

How close is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock to the airport?

This vacation home is 30.4 mi (46-min drive) away from the Easton, MD (ESN-Easton - Newnam) airport, the closest popular airport to the property.

Does Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock to the beach?

This vacation home is on the beach. Don't forget your sunscreen!

Does Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock?

No, there is no casino at this vacation home.

What time is check-in at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock?

Check-in begins at 4:00 PM.

Is there free parking at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock?

Free parking is not available at this vacation home.

Does Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock have a pool?

This vacation home features an outdoor pool.

Does Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock have a spa?

This vacation home doesn't have a spa, but it does offer massages.

How close is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock to downtown Woolford?

This vacation home is 2.8 mi away from Woolford.