Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock | House in Woolford

9.8 (74 Reviews) |   Pet Friendly   7 Bedrooms  5 Bathrooms  18 Guests
Woolford House | Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

7 Bedroom House in Woolford

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

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock is located in Woolford. Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock provides accommodation, featuring TV, Bedding/Linens, Spa, among other amenities. This House features TV, Bedding/Linens, Spa, to make your stay a comfortable one.

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock has 7 Bedrooms , 5 Bathrooms, and max occupancy of 18 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Woolford has interesting places to visit. If you want to learn more about the House in Woolford, such as places to visit and things to do nearby, you can check below to learn more.

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Woolford, 21677, USA

Amenities

Air Conditioner
Parking
Pet Friendly
Pool
TV
View
Private Pool
Ocean View
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Spa
Fireplace/Heating
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Soap
  • Bathtub or shower
  • Shampoo
  • Toilet paper
  • 5 bathrooms
  • Jetted bathtub
  • Towels provided
  • Hair dryer
Bedroom
  • Sofa bed
  • Bed sheets provided
  • 7 bedrooms
  • Dining table
  • Living room
  • Dining room
  • Fireplace
Kitchen
  • Stovetop
  • Ice maker
  • Refrigerator
  • Paper towels
  • Microwave
  • Spices
  • Oven
  • Toaster
  • Dishwasher
Laundry
  • Laundry facilities
  • Washing machine and dryer
  • Near laundromat
Ocean view
  • Beach sun loungers
  • On the beach
  • Beach towels
Parking
  • Onsite parking
  • Car required
Pet Friendly
  • Welcoming dogs only
  • 1 total (up to 50 lbs per pet)
  • Pet friendly
Accessibility
  • Note from host: We take this seriously, thanks
  • Smoke-free property
Activities
  • Golf privileges
  • Kayak on site
  • Cycling nearby
  • Water skiing nearby
  • Boat on site
  • Bicycle on site
  • Hunting nearby
  • Fitness facilities nearby
  • Golfing on site
  • Hiking nearby
  • Power boating nearby
  • Swimming nearby
  • Water sports equipment
  • Birdwatching nearby
  • Water tubing nearby
  • Ecotours nearby
  • Tennis on site
Entertainment
  • Table tennis
  • Foosball table
  • Arcade/game room
  • Games
  • Books
  • Smart TV with cable/satellite service
  • Stereo
  • DVD player
General
  • Unit size: 5400 sq ft (502 sq m)
  • Spanish
  • English
  • Near the bay
  • In a rural location
  • Near a health or beauty spa
  • Near a hospital
  • In the city center
  • Near outlet shopping
  • On the waterfront
  • On the lake
  • Office
  • Desk
  • Desk chair
Guest Services
  • Stair gate
  • Children's dinnerware
  • Children's toys
  • Children's books
  • Babysitting service available
  • Playground
  • Children's games
  • Iron/ironing board
  • Chef
  • Local meal delivery service
  • Concierge services
Internet
  • Free WiFi
Outdoors
  • Fenced yard
  • Balcony
  • Barbecue grill
  • Outdoor furniture
  • Garden
  • Dock
  • Firepit
Security/Safety
  • Fire extinguisher
  • First aid kit
  • Deadbolt lock
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
Spa
  • Fence around the pool
  • Outdoor pool
  • Private pool
  • Heated pool
  • Massages
  • Hot tub
  • Sauna

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
Child Policy
Children are welcome. note from host: love kids! house designed with a kids' floor!
Event Policy
No events allowed;only small, indoor parties
Pet Policy
1 total (up to 50 lbs per pet) note from host: must ask at booking. a fee plus deposit required. pets allowed restrictions apply; for more information contact the property at the number on the booking confirmation service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy
Smoking is not permitted;we take this seriously, thanks
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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property note from host: only small, indoor parties onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

Ronald S.
Jun 1, 2025 11:43:50 PM
Review Score:   10
Summary: We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we even found a restaurant on our side of the bridge that could seat all 16 of us for seafood. If you need a beautiful house in an equally lovely Eastern Shore setting, you will be happy with this one.
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FAQ's

Is this Woolford house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Woolford house have a swimming pool?

Yes, this Woolford house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Woolford house?

Best-rates for the Woolford house starts from $942 per night with includes Fireplace/Heating, Internet, Kitchen, Parking, Ocean View, Security/Safety, Pool, View, Balcony/Terrace, Sports/Activities, Wellness Facilities, Entertainment, Barbecue/Outdoor Cooking, Child Friendly, Air Conditioner, Pet Friendly, Private Pool, Guest Services, Hot Tub, Laundry, TV, Bedding/Linens, Spa with all other facilities. BedroomVillas.com.au matches every traveler with their perfect villa, resort, or rental and whether you are traveling with a group, friends, family, or pets.

Is Woolford house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Woolford house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Woolford house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Woolford house?

Based on the information reported by the owner or manager, the Woolford house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Woolford house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Woolford house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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