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

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Lake
Property grounds
Exterior
1 bedroom, desk, iron/ironing board, travel crib
Interior
Reviews
9.8

Exceptional

Entire home

1 bedroom5 bathroomsSleeps 185400 sq ft

Popular amenities

  • Hot TubHot TubHot Tub
  • FireplaceFireplaceFireplace
  • Pet friendlyPet friendlyPet friendly
  • PoolPoolPool
  • KitchenKitchenKitchen
  • Barbecue grillBarbecue grillBarbecue grill

Explore the area

Map
Woolford, MD
  • Popular LocationHarriet Tubman Museum and Educational Center21 min drive
  • Popular LocationChoptank River Lighthouse23 min drive
  • Popular LocationLong Wharf Park23 min drive
  • AirportEaston, MD (ESN-Easton - Newnam)46 min drive

Room options

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 State Park Visitors Center. Harriet Tubman Underground Railroad National Historical Park is within 9 miles (15 km) and Harriet Tubman Museum and Educational Center is within 12 miles (20 km).

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

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

** 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 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

Property manager

John

Languages

English, Spanish

Property amenities

Beach

  • On the beach
  • Beach loungers
  • Beach towels

Pool/Spa

  • Fenced private pool
  • Heated pool
  • Massage
  • Outdoor pool
  • Sauna
  • Spa tub

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

  • Bedroom
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Jetted bathtub
  • Jetted bathtub
  • Shampoo
  • 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
  • Fenced yard
  • Firepit
  • Garden
  • Outdoor furniture

Laundry

  • Laundromat nearby
  • 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

  • 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 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 on site
  • Bicycles on site
  • Boat on site
  • Foosball table on site
  • Golf on site
  • Heated pool on site
  • Kayak on site
  • Optional golf privileges on site
  • Table tennis on site
  • Tennis
  • Water sports equipment on site
  • 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

  • 1 unit
  • 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

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!

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. Contactless check-in and contactless check-out are available.

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.

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 60 out of 67 reviews" "
Rating 8 - Good. 6 out of 67 reviews" "
Rating 6 - Okay. 0 out of 67 reviews" "
Rating 4 - Poor. 0 out of 67 reviews" "
Rating 2 - Terrible. 1 out of 67 reviews" "

9.4/10

Cleanliness

Reviews

10/10 Excellent

Michael B.

Liked: Cleanliness
Chesapeake Family Vacation
Wonderful house. Well stocked with supplies. Great open floor plan along with a couple separate spaces on the main floor. Our group had 7 adults and our eight grandchildren six and under. Pool has gated access which was a key feature with all our little ones. The owner provided much info regarding things to do in the area. The bedroom spaces worked out great with our mix. We really enjoyed the crab traps and the dock for fishing. It was mostly casting practice but the kids loved it. We enjoyed the fire pit in the evening. It is a relatively secluded location but within a couple miles of a country store and seafood market and about 10 miles from the town of Caimbridge with a Walmart for any shopping needs. I would highly recommend this for a family vacation like we had.
Stayed 7 nights in May 2024

10/10 Excellent

Christine F.

Liked: Cleanliness
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
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
woolford
great property!
Stayed 7 nights in Aug 2023

10/10 Excellent

Jean M.

Liked: Cleanliness
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
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

10/10 Excellent

William P.

Liked: Cleanliness
Saddlebeach
We absolutely enjoyed our stay at Saddlebeach. The house and grounds were everything we were hoping for and more. There were 15 of us- 10 adults and 5 kids ranging in age from 2 to 10. There was plenty of bedroom and bathroom space. The children were especially happy to have the pool to jump into and the dock to fish from. The list of restaurants Jon provided was very useful - we found Old Salty's which we really liked. We all had a wonderful time and are looking forward to coming back next summer
Stayed 7 nights in Jul 2023

10/10 Excellent

Carol N., Smith Mountain Lake, Va.

Liked: Cleanliness
Sunshine, dolphins and campfire, oh my!
Great for families, and we have a big one. 8 adults and 7 kids (2 to 11 year olds) and plenty of room for all.
Stayed 4 nights in Apr 2023

10/10 Excellent

Amy K.

Liked: Cleanliness
Gorgeous property, Great hosts
We ended up at Jon's property b/c our original VRBO had a last minute utility breakage that wasn't going to be able to be fixed by the time of our arrival. Being good neighbors (which says a lot), they worked with Jon to offer us a comparable stay on this property instead. The communication & amount of helpful detail on the area that I got from Jon FAR exceeded anything I've had from other rentals anywhere, and his outreach was not only super detailed, but personable & friendly, by text, email and by phone. If you're wondering what you're going to "do" in the area, go ahead & rent & when Jon sends you his list of things in the area you won't wonder any more. I wish this host had properties elsewhere in the US too! The property itself is GORGEOUS - I hope occasion will bring our group back again at another time to explore other seasons. Sufficiently isolated to feel free & easy, yet close enough to town for meals out every night if we wanted (and a big ol kitchen if we didn't), this place really has it all, and every person in my group was pleased. It's a bit odd for paper products to not be already available, but Walmart is easy, and the property is a bit further from BWI than we would have liked, but you don't get gorgeous countryside right near an international airport. Totally worth it :) It was March when our group travelled, and I bet the lakefront & surrounding areas are even more beautiful in the summer & fall. Definitely recommended, would absolutely rent again.
Stayed 4 nights in Mar 2023

8/10 Good

Chris L., Pittsburgh, PA

Liked: Cleanliness
Christmas Holiday Family Getaway
Saddle Beach was roomy, well equipped and very comfortable for our Family Holiday getaway! We enjoyed card & board games by the indoor gas fireplace, and talks around the outdoor fire pit. Cornhole games, long walks/runs, and trips to the wildlife refuge and Tubman Museum filled out the week. Good times for all!
Stayed 11 nights in Dec 2022