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"Endless Summer" Waterfront on the Chesapeake Bay!

2.0 star property
Woolford vacation home with private pool

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Photo gallery for "Endless Summer" Waterfront on the Chesapeake Bay!

Interior
Exterior
Fridge, microwave, oven, stovetop
Terrace/patio
Smart TV, foosball

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Pool
  • Barbecue grill
  • Parking available

Explore the area

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

Room options

About the neighborhood

Woolford

In Woolford .You'll be within 9 miles (15 km) of Blackwater National Wildlife Refuge and 12 miles (20 km) of Harriet Tubman Underground Railroad National Historical Park. Harriet Tubman State Park Visitors Center and Christ Rock Park are within 12 miles (20 km).
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What's nearby

  • Blackwater National Wildlife Refuge - 18 min drive - 7.5 miles
  • Harriet Tubman Museum and Educational Center - 29 min drive - 14.7 miles
  • Choptank River Lighthouse - 30 min drive - 15.1 miles
  • Long Wharf Park - 30 min drive - 15.1 miles
  • Gerry Boyle Park at Great Marsh - 32 min drive - 15.8 miles

Getting around

  • Cambridge Station - 21 min drive
  • Easton, MD (ESN-Easton - Newnam) - 43 min drive

Restaurants

  • ‪Madison Bay - ‬9 min drive
  • ‪Woolford General Store - ‬9 min drive
  • ‪The Neck District Grill - ‬39 min drive
  • ‪Maryland Blue - ‬9 min drive
  • ‪Marley's Cafe - ‬9 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.

"Endless Summer" Waterfront on the Chesapeake Bay!

A private waterfront Oasis! This exceptional 4 bedroom, 3 bathroom Rural waterfront Eastern Shore home sits on over 6 acres and boast endless water activities, including an indoor heated pool! Along with kayaking, crabbing or fishing. You can drift off to sleep to sounds of nature and resting geese in the oversized main suite with a perfect waterfront view! Enjoy the Eastern Shore lifestyle in this beautiful backyard, complete with mesmerizing views and a firepit.
Crab or fish from the pier for dinner or take in an amazing sunset!
The property even has access to a sandy Beach to sit and relax with your favorite beverage. Amazing wildlife on the property to enjoy and admire which include two different species of deer, herrings, bald eagles and ospreys!
If this isn't enough you are only minutes from the Blackwater National Wildlife Refuge. Additionally the Harriet Tubman museum is located directly next to the Blackwater Refuge. Take in the local seafood at nearby waterfront restaurants, explore the beautiful nature that the area has to offer and take a well deserved break from the daily grind. You will have access to the property managers direct phone number to during your stay to assist with any questions or issues should they arise. No more waiting on endless email responses, text messages or voicemails from a large rental company. We strive to make your stay a memorable one! So don't hesitate and book now for a unforgettable Chesapeake Bay experience on Marylands Eastern Shore!

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Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
  • Kitchen
  • Washer
  • Dryer
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4.9 out of 5, Exceptional, 133 reviews
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Property amenities

Pool/Spa

  • Heated pool
  • Indoor pool
  • Private pool

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Separate dining area

Entertainment

  • Smart TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • Smoking not allowed

Things to do

  • Foosball table
  • Heated pool
  • Kayak

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)

Policies

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 pets
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

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
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
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 professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.

Frequently asked questions

How close is "Endless Summer" Waterfront on the Chesapeake Bay! to the airport?

This vacation home is 31.2 mi (43-min drive) away from the Easton, MD (ESN-Easton - Newnam) airport, the closest popular airport to the property.

Does "Endless Summer" Waterfront on the Chesapeake Bay! have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does "Endless Summer" Waterfront on the Chesapeake Bay! offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at "Endless Summer" Waterfront on the Chesapeake Bay!?

No, there is no casino at this vacation home.

Is there free parking at "Endless Summer" Waterfront on the Chesapeake Bay!?

Free parking is not available at this vacation home.

Does "Endless Summer" Waterfront on the Chesapeake Bay! have a pool?

This vacation home features an indoor pool.

Does "Endless Summer" Waterfront on the Chesapeake Bay! have a spa?

There are no spa services available at this vacation home.

How close is "Endless Summer" Waterfront on the Chesapeake Bay! to downtown Woolford?

This vacation home is 3.1 mi away from Woolford.

Reviews

"Endless Summer" Waterfront on the Chesapeake Bay! Reviews

10

Exceptional

9.6/10

Cleanliness
Rating 10 - Excellent. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

Reviews

10/10 Excellent

Tuan N.

Liked: Cleanliness
Perfect water front location for seclusion, quiet fishing and crabbing on the pier and late night fire pits!
Stayed 3 nights in Oct 2025

10/10 Excellent

Christopher T.

Liked: Cleanliness
Great location
Stayed 3 nights in Sep 2025

10/10 Excellent

Dov K.

Liked: Cleanliness
All was great
Stayed 8 nights in Aug 2025

10/10 Excellent

Jennifer B., Southwest PA

Liked: Cleanliness
We wanted a restful, peaceful break without crowds, and this rental was perfect in those and many other respects. The host was very helpful and accommodating with a few questions we had upon arrival, and he worked hard to make sure our stay was perfect. The house and property are beautiful and spacious. Housekeeping was excellent—all the floors, surfaces, drawers, and shelves were exceptionally clean, and having high-quality linens and towels already in place was wonderful. The kitchen has plenty of cookware, utensils, new tableware, and storage. The master suite is enormous; it has a beautiful bathroom with great lighting and features. The views from the house, deck, pool, and dock were amazing. The dock appears to be brand new and was perfect for coffee or wine walks and watching the sunrise. There are several spots to launch the kayaks from the shore, and the water was calm enough for even a novice like me to handle paddling. We saw many kinds of shore birds, and deer and foxes came right through the yard. From the dock, we saw crabs, fish, and a cownose ray. The lane out to the main road is great for a quiet walk. We were grateful to have the pool for cooling off. The Woolford Store is only about 3 miles away -- great cheesesteaks and sandwiches! They have bug spray and other supplies, as well. We would strongly recommend this rental if you are looking for peace, quiet, and the opportunity to connect/reconnect with family and nature.
Stayed 4 nights in Jul 2025