Entire home
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
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Reviews
9.8 out of 10, Loved by Guests
Top 10% based on
7 bedrooms5 bathroomsSleeps 18501.7 sq m
Popular amenities
Explore the area

Woolford, MD
- Place, Blackwater National Wildlife Refuge12 min drive
- Place, Harriet Tubman Underground Railroad National Historical Park17 min drive
- Place, Harriet Tubman Museum and Educational Center21 min drive
- Airport, Easton, MD (ESN-Easton - Newnam)48 min drive
Rooms & beds
7 bedrooms (sleeps 18)
3rd Floor Full's Bedroom
2 Double Beds
3rd Floor Twins Bedroom
+1
5 Single Beds
First Floor Den/Bdrm
1 Double Sofa Bed
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 Bath
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo
Ground Floor Bath
Soap · Towels provided · Bathtub or shower · Toilet · Shower only · Shampoo · Hair dryer
Guest Suite 1 Bath
Soap · Towels provided · Bathtub or shower · Toilet · Shower only · Shampoo · Hair dryer
Guest Suite 2 Bath
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer
Huge Master Bath
+1
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Jetted bathtub · Shampoo · Hair dryer
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, Dock Pet permitted
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- Pool
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- Washing machine
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10.0 out of 10, Exceptional, (31 reviews)
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 23 kg 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
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
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. The area's natural beauty can be seen at Blackwater National Wildlife Refuge and Bill Burton Fishing Pier State Park, while Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center are cultural highlights. Travelling with kids? Consider Richardson Maritime Museum and Dorchester Arts Center. Jet skiing and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and hiking nearby.

Woolford, MD
What's nearby
- Blackwater National Wildlife Refuge - 12 min drive - 11.4 km
- Harriet Tubman Underground Railroad National Historical Park - 17 min drive - 17.7 km
- Harriet Tubman Museum and Educational Center - 21 min drive - 23.0 km
- Dorchester County Visitors Center - 22 min drive - 23.7 km
- Choptank River Lighthouse - 22 min drive - 23.6 km
Getting around
Restaurants
- Madison Bay - 8 min drive
- Woolford General Store - 8 min drive
- Boats & Hose - 16 min drive
- Church Creek Cafe - 12 min drive
- The Neck District Grill - 36 min drive
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.6/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
1 December 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in Nov 2025
Verified
10/10 Excellent
Michael E.
12 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Michael E.
Stayed 7 nights in Aug 2025
Verified
10/10 Excellent
Linda S.
24 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Linda S.
Stayed 7 nights in Aug 2025
Verified
10/10 Excellent
Lauren I.
23 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay!
Lauren I.
Stayed 7 nights in Jun 2024
Verified
10/10 Excellent
Susan G.
29 May 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family fun
Susan G.
Stayed 3 nights in May 2021
Verified
10/10 Excellent
Kerry N.
27 June 2020
Liked: Check-in, communication, location, listing accuracy
Great Stay!
Kerry N.
Stayed 7 nights in Jun 2020
Verified
10/10 Excellent
Carol N.
11 April 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Sunshine, dolphins and campfire, oh my!
Carol N.
Stayed 4 nights in Apr 2023
Verified
10/10 Excellent
Lindsay W.
29 August 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
woolford
Lindsay W.
Stayed 7 nights in Aug 2023
Verified
10/10 Excellent
Christine F.
5 December 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Weekend Getaway
Christine F.
Stayed 2 nights in Dec 2023
Verified
10/10 Excellent
Beth H.
22 July 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Saddlebeach Property
Beth H.
Stayed 7 nights in Jul 2020
Verified
10/10 Excellent
Ronald S.
1 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely home, well-outfitted for a big group
Ronald S.
Stayed 4 nights in May 2025
Verified
10/10 Excellent
evan w.
30 August 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful setting and plenty of space
evan w.
Stayed 7 nights in Aug 2022
Verified
10/10 Excellent
LISA S.
25 July 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Vacation on the bay
LISA S.
Stayed 7 nights in Jul 2020
Verified
8/10 Good
Chris L.
18 January 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Christmas Holiday Family Getaway
Chris L.
Stayed 11 nights in Dec 2022
Verified
10/10 Excellent
Mark S.
16 January 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Eastern Shore Respite
Mark S.
Stayed 3 nights in Jan 2023
Verified
10/10 Excellent
Jennifer Z.
28 November 2018
Outstanding!
Jennifer Z.
Stayed 3 nights in Nov 2018
Verified
10/10 Excellent
Anthony D.
25 April 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
80th Birthday Celebration
Anthony D.
Stayed 3 nights in Apr 2022
Verified
10/10 Excellent
John B.
23 July 2022
Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness
Great house for a large group
John B.
Stayed 7 nights in Jul 2022
Verified
10/10 Excellent
John F.
1 December 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice escape in the Chesapeake
John F.
Stayed 3 nights in Nov 2020
Verified
10/10 Excellent
cathy L.
16 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Vacation paradise
cathy L.
Stayed 7 nights in Jul 2024
Verified
10/10 Excellent
William P.
27 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Saddlebeach
William P.
Stayed 7 nights in Jul 2023
Verified
10/10 Excellent
F.E. and Diane M.
9 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family, Fun, Fishing
F.E. and Diane M.
Stayed 7 nights in Jul 2022
Verified
10/10 Excellent
Jean M.
7 August 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Family Vacation
Jean M.
Stayed 7 nights in Jul 2023
Verified
10/10 Excellent
Charlotte B.
13 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Home, Breathtaking views, amazing host
Charlotte B.
Stayed 3 nights in Apr 2022
Verified
10/10 Excellent
Gene C.
6 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
As advertised
Gene C.
Stayed 7 nights in Jun 2022
About the host
Hosted by John
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
They consistently provide great experiences for their guests
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