See all properties
Entire home

"Endless Summer" Waterfront on the Chesapeake Bay!

Choose dates to view prices

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

Exterior
Smart TV, foosball
Terrace/patio
Indoor pool, a heated pool
Fridge, microwave, oven, stovetop

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning

Explore the area

View in a map
Woolford, MD
  • Place, Blackwater National Wildlife Refuge
    ‪13 min drive‬
  • Place, Harriet Tubman Underground Railroad National Historical Park
    ‪18 min drive‬
  • Place, Harriet Tubman Museum and Educational Center
    ‪22 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪49 min drive‬

Room options

About the neighborhood

Woolford

This vacation home is located 6.3 mi (10.1 km) from Blackwater National Wildlife Refuge and 9.3 mi (15 km) from Harriet Tubman Underground Railroad National Historical Park. The vacation home includes a private pool, a kitchen, and a patio.
View more Vacation Homes in WoolfordOpens in a new window

What's nearby

  • Blackwater National Wildlife Refuge - 13 min drive - 7.5 miles
  • Christ Rock Park - 17 min drive - 11.1 miles
  • Harriet Tubman Underground Railroad National Historical Park - 18 min drive - 11.5 miles
  • Harriet Tubman Museum and Educational Center - 22 min drive - 14.7 miles
  • Choptank River Lighthouse - 23 min drive - 15.1 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
  • ‪Church Creek Cafe - ‬13 min drive
  • ‪Soft & Salty Seafood - ‬47 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!
The vacation home is air-conditioned and features a kitchen, 3 bathrooms, and a patio. There's space to spread out with 4 bedrooms and a dining area. Other standard amenities include a private pool, a washing machine, and a coffee maker.

Similar properties

Meeting facility
Historic Inns of Annapolis
Historic District
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
9.0 out of 10, Wonderful, 1,842 reviews
$173 nightly
The price is $197
May 25 - May 26
Total with taxes and fees
Historic Inns of Annapolis

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
Information provided by the property may be translated using automated translation tools

Pets

  • This property welcomes pets
  • Dogs only
  • 1 total pets
  • Service animals exempt from fees

Children and extra beds

Children allowed: ages 0-17

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

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector and a smoke detector.

Frequently asked questions

What is there to do close to this vacation home?

This vacation home is located in Woolford, close to Ragged Island, Spocott Windmill, and Christ Rock Park.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

Yes, this vacation home has an indoor pool.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay free of charge?

Although dogs can't stay for free, they are welcome at this vacation home.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is Easton, MD (ESN-Easton - Newnam), which is about 20.6 mi away.

"Endless Summer" Waterfront on the Chesapeake Bay! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 7 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Shana M.

Liked: Cleanliness
Amazing property with an amazing view. Kids had a great time playing in the pool and the dog had fun exploring the property.
Stayed 4 nights in Apr 2026

10/10 Excellent

J H.

Liked: Cleanliness
We had a great visit at “Endless Summer “. Everything was as advertised. House, pool and property were great. Enjoyed seeing eagles on the dock in the mornings. Communication with the host was timely and helpful.
Stayed 6 nights in Dec 2025

10/10 Excellent

Jennifer H., Glen Allen, USA

Liked: Cleanliness
The host was very responsive and helpful when we had requests (to change our check in day). The house is wonderfully spacious- as good as the pictures. The weather was cold as it was Thanksgiving, but the pool was comfortable, and we enjoyed Smores at the firepit (we brought our own firewood (there are plenty of twigs for kindling, but not large pieces of wood on the grounds). Linens provided were clean, soft, and plentiful. Views and seclusion are exceptional. We are a group of 4 adults and 5 teenagers, and we were very comfortable in the home. The foosball table got plenty of use, and the large couch and big flat, adjustable tv were great for movie watching. Would happily start again. I recommend bringing your own paper products, Tupperware, and dish soap & pods if you are staying more than a couple days and mostly cook in.
Stayed 4 nights in Nov 2025

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