Entire home
"Endless Summer" Waterfront on the Chesapeake Bay!
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Reviews
10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 12
Popular amenities
Rooms & beds
4 bedrooms (sleeps 12)
Bunk Room
2 Single Bunk Beds
Master Suite
1 King Bed
Queen
1 Queen Bed
Queen
1 Queen Bed
3 bathrooms
Bathroom 1
Bathroom 2
Bathroom 3
Spaces
Deck or patio
Kitchen
Separate dining area
Dining area
About this property
"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!
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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10.0 out of 10, Exceptional, (58 reviews)
House Rules
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs (limit 1 total)
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
On-site parties or group events are strictly prohibited
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
About the area
Woolford
Woolford is home to this holiday home. Harriet Tubman Underground Railroad National Historical Park and Choptank River Lighthouse are local landmarks, and the area's natural beauty can be seen at Blackwater National Wildlife Refuge and Bill Burton Fishing Pier State Park. Richardson Maritime Museum and Dorchester Arts Center are also worth visiting.
Woolford, MD
What's nearby
- Blackwater National Wildlife Refuge - 13 min drive - 12.0 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
- Dorchester County Visitors Center - 23 min drive - 24.4 km
- Gerry Boyle Park at Great Marsh - 25 min drive - 25.3 km
Getting around
Restaurants
- Madison Bay - 9 min drive
- Woolford General Store - 9 min drive
- Church Creek Cafe - 13 min drive
- The Neck District Grill - 39 min drive
- Millie's at Madison Bay - 9 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.8/10
Cleanliness
9.8/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
Verified
2 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Sep 2025
Verified
10/10 Excellent
J H.
30 Dec, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
J H.
Stayed 6 nights in Dec 2025
Verified
10/10 Excellent
Tuan N.
13 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tuan N.
Stayed 3 nights in Oct 2025
Verified
10/10 Excellent
Dov K.
7 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Dov K.
Stayed 8 nights in Aug 2025
Verified
10/10 Excellent
Jennifer H.
30 Nov, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Jennifer H.
Stayed 4 nights in Nov 2025
Verified
10/10 Excellent
Jennifer B.
14 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jennifer B.
Stayed 4 nights in Jul 2025
About the host
Hosted by Doug Parks
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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