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"Endless Summer" Waterfront on the Chesapeake Bay!

2.0 star property
Vacation home in Woolford with private pool and kitchen

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

Interior - "Endless Summer" Waterfront on the Chesapeake Bay! (Woolford)
Terrace/patio - "Endless Summer" Waterfront on the Chesapeake Bay! (Woolford)
Fridge, microwave, oven, stovetop - "Endless Summer" Waterfront on the Chesapeake Bay! (Woolford)
Exterior - "Endless Summer" Waterfront on the Chesapeake Bay! (Woolford)
Smart TV, foosball - "Endless Summer" Waterfront on the Chesapeake Bay! (Woolford)
Escape to a serene waterfront oasis at this Eastern Shore retreat. With an indoor heated pool, kayaking, and crabbing, endless water activities await. Drift off to sleep with sounds of nature in the oversized main suite with perfect waterfront views.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms

Popular amenities

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

Add dates for prices

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!

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)

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Policies

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total pets

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

About the neighborhood

Map
Woolford, MD

What's nearby

  • Blackwater National Wildlife Refuge - 13 min drive - 12.0 km
  • Harriet Tubman State Park Visitors Center - 17 min drive - 17.7 km
  • Harriet Tubman Underground Railroad National Historical Park - 18 min drive - 18.4 km
  • Harriet Tubman Museum and Educational Center - 22 min drive - 23.6 km
  • Choptank River Lighthouse - 23 min drive - 24.3 km

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
  • ‪Church Creek Cafe - ‬13 min drive
  • ‪Maryland Blue - ‬9 min drive

Frequently asked questions

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

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

Is "Endless Summer" Waterfront on the Chesapeake Bay! pet-friendly?

Yes, this property allows dogs (limit 1 total).

How much is parking?

Onsite parking is available at the property.

Where is "Endless Summer" Waterfront on the Chesapeake Bay! located?

Situated in Woolford, this vacation home is within 12 mi (20 km) of Blackwater National Wildlife Refuge, Harriet Tubman Underground Railroad National Historical Park, and Harriet Tubman State Park Visitors Center. Christ Rock Park and Snows Turn Park are also within 12 mi (20 km).

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Reviews

"Endless Summer" Waterfront on the Chesapeake Bay! Reviews

10

Exceptional

9.6

Cleanliness

10

Location
Rating 10 - Excellent. 5 out of 5 reviews
Rating 8 - Good. 0 out of 5 reviews
Rating 6 - Okay. 0 out of 5 reviews
Rating 4 - Poor. 0 out of 5 reviews
Rating 2 - Terrible. 0 out of 5 reviews

Reviews

10/10 Excellent

Dov K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
All was great
Stayed 8 nights in Aug 2025

10/10 Excellent

Jennifer B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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