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Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock - Free Night thru April

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock - Free Night thru April

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

Our home blends into towering pines, lawns & hundreds of feet of waterfront
Gorgeous pool just off the kitchen /porch
One of two beach areas on the property.  Shown at low tide.
Exterior
House + Pool + Lawns + + pond + waterfront

Overview of Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock - Free Night thru April

Reviews
9.8 out of 10 Exceptional
7 bedrooms5 bathroomsSleeps 18502 sq m

Popular amenities

  • PoolPoolPool
  • Hot tubHot tubHot tub
  • FireplaceFireplaceFireplace
  • Pet-friendlyPet-friendlyPet-friendly
  • KitchenKitchenKitchen
  • Barbecue grillBarbecue grillBarbecue grill

Check out the area

Map
Woolford, MD
  • Popular LocationHarriet Tubman Underground Railroad National Historical Park18 min drive
  • Popular LocationHarriet Tubman Museum and Educational Center21 min drive
  • Popular LocationChoptank River Lighthouse23 min drive
  • AirportEaston, MD (ESN-Easton - Newnam)46 min drive

Rooms & beds

7 bedrooms (sleeps 18)

3rd Floor Bedroom Fulls

2 Double Beds

3rd Floor Twins Bedroom

+1
5 Single Beds

First Floor Den/Bdrm

1 Double Futon

Guest Room 2nd Floor

2 Single Beds

Guest Suite 2nd Floor

1 Queen Bed

Guest Suite 2nd Floor

1 Queen Bed

Master 2nd Floor

1 King Bed

5 bathrooms

3rd Floor Suite

Bathtub · Toilet

Ground Floor

Toilet · Shower only

Guest Suite 1

Toilet · Shower only

Guest Suite 2

Bathtub or shower · Toilet

Master

Bathtub · Toilet · Shower only · Jetted bathtub

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Balcony
Separate dining area
Outdoor play area
Garden
Dining Area

About this property

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock - Free Night thru April

** Pool open April 1 - Book 3 nights get the 4th FREE through April **
Families and groups LOVE our 7 Bedroom, 5 Bath luxury property

5+ acres, 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 loblolly 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
** - 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

Property manager

John
Premier Host
Premier Host

Languages

English, Spanish
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Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Pet-friendly

House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 10:30 AM

Children

Children allowed: ages 0–17
Love kids! House designed with a kids' floor!

Events

No events allowed
Only small, indoor parties

Pets

Pets allowed: dogs less than 50 lb per pet (limit one pet total)
Must ask at booking. A fee plus deposit required.

Smoking

Smoking is not permitted
We take this seriously, thanks
Signed rental agreement required. See full house rules thanks.
Security: WiFi door lock for convenience for you & your guests. Exterior security cameras onsite; facing driveway & water.
Pets: 1 dog. Not allowed on furniture or off-leash. Add. refundable deposit required + a pet fee. Required to manage turnaround for the next guest

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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

We should mention

A car is required for transport to and from this property

About the area

Woolford

Located in Woolford, this holiday home is in the city centre and on the beach. Choptank River Lighthouse and Cove Point Lighthouse are local landmarks, and some of the area's activities can be experienced at Layton's Chance Vineyard and Winery and St. Michaels Winery. Travelling with kids? Consider Richardson Maritime Museum and Ruark Boatworks. Jet skiing and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby.
Map
Woolford, MD

What's nearby

  • Harriet Tubman Underground Railroad National Historical Park - 18 min drive
  • Harriet Tubman Museum and Educational Center - 21 min drive
  • Choptank River Lighthouse - 23 min drive
  • Long Wharf Park - 23 min drive
  • Dorchester County Visitors Center - 23 min drive

Getting around

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

Restaurants

  • Lindy's Seafood - 7 min drive
  • Woolford Country Store - 8 min drive
  • Madison Bay Rnr - 8 min drive
  • Mc Cray's Castaways - 8 min drive
  • Palm Beach Willies - 15 min drive

Frequently asked questions

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

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock - Free Night thru April pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 50 lb per pet.

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

Check-in begins at 4:00 PM.

What time is check-out at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock - Free Night thru April?

Checkout is at 10:30 AM.

Where is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock - Free Night thru April located?

Located in Woolford, this beachfront holiday home is in the city centre and within 9 mi (15 km) of Blackwater National Wildlife Refuge, Harriet Tubman State Park Visitors Center and Harriet Tubman Underground Railroad National Historical Park. Long Wharf Park and Harriet Tubman Museum and Educational Center are also within 12 miles (20 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 59 out of 66 reviews" "
Rating 8 - Good. 6 out of 66 reviews" "
Rating 6 - Okay. 0 out of 66 reviews" "
Rating 4 - Poor. 0 out of 66 reviews" "
Rating 2 - Terrible. 1 out of 66 reviews" "

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Christine F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Dec 2023

10/10 Excellent

Robin Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!!
Stayed 3 nights in Oct 2023

10/10 Excellent

Lindsay W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
woolford
great property!
Stayed 7 nights in Aug 2023

10/10 Excellent

Jean M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Family Vacation
We couldn't have asked for a better vacation. The house was large enough to accommodate all 11 of us and had enough space that we didn't feel on top of each other. The kids loved the 3rd floor zone. The house was well equipped with everything we needed for a fun time. The dock was perfect for catching fish, crabs, and even rays. The kayaks were great for early morning or late afternoon rides. The pool was huge and allowed us to cool off. The host was very responsive to our questions. We enjoyed it so much we've already booked the house for next year.
Stayed 7 nights in Jul 2023

10/10 Excellent

Joanne A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Jul 2023

About the host

Hosted by John

Host profile image
At first we rented out Saddle Beach a few weeks each summer to offset cost. Now we spend most of our time on the West Coast. Home is rented weekly in summer and weekends throughout the year. It's tough to be far away but we're still there often! Our full-time caretakers, Teri and Ken are wonderful and frankly, amazing. We also have a support group of great local vendors and contractors whose families have been the area for generations. We love to help create vacation memories. Let us help you plan a great stay – enjy the property but you've got the potion to see the area as well. Go biking, hiking, sightseeing, crabbing, fish and boat around the area! Try the local restaurants and drive through the countryside – we have the areas only national wildlife refuge just 15 minutes away. Ask, ask ask! We want to help you plan! We have several repeat visitors each year. We are a real family and we have tremendous experience enabling family and similar vacations. We really do enjoy helping others make their own vacation memories on the Eastern Shore and the Chesapeake Region.

Why they chose this property

Size, beauty, location and amenities. Saddle Beach is the perfect vacation home for extended families and groups. It's gorgeous, with everything you need for best experience > on the property... or venture out to countless attractions, restaurants and recreation. Classic, private wraparound porches are a dream... The home was built with meticulous detail and an open floor plan, yet everyone says it feels warm and inviting. We built it for our family after a decade of planning. The property is expansive and private and invites a week-long family event much like the family compounds of New England. It's a luxury property on the most elegant enclave of fine homes in the county, yet only ten minutes from the town of Cambridge, Maryland. The water is wide, calm and simply gorgeous! The Chesapeake Bay region is rural and water is everywhere.

What makes this property unique

You'll fall in love with the deep, stone wrap around porches, hand-cut, reclaimed walnut floors, and yet find it hard to stay inside with your own private pool, beach, dock, tidal pond and estate grounds.

Languages:

English, Spanish

Premier Host

Premier Host
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