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"Endless Summer" Waterfront on the Chesapeake Bay!

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

A sunset over a calm body of water with a pier extending into the water.
Miscellaneous
A wooden deck leading to a grassy area with a view of a body of water and a distant shoreline.
A wooden pier leading to a house by a calm body of water, surrounded by trees and grassy areas.
A wooden pier extending into calm water with clear skies above.

Reviews

9.8 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Heated pool
    Swim in comfort year-round in the heated pool, a rare find in this location.
4 bedrooms3 bathroomsSleeps 12

Popular amenities

  • Private pool
  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View map
Woolford, MD
  • Place, Blackwater National Wildlife Refuge
    ‪8 min drive‬
  • Place, Christ Rock Park
    ‪17 min drive‬
  • Place, Harriet Tubman Underground Railroad National Historical Park
    ‪19 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪60 min drive‬

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!

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House Rules

Check in after 4:00 PM
Minimum age to rent: 24
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 1 total)
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 4218261vb
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.
View more Holiday homes in WoolfordOpens in a new window
Map
Woolford, MD

What's nearby

  • Blackwater National Wildlife Refuge - 8 min drive - 7.2 km
  • Christ Rock Park - 17 min drive - 17.8 km
  • Harriet Tubman Underground Railroad National Historical Park - 19 min drive - 19.1 km
  • Harriet Tubman Museum and Educational Center - 23 min drive - 23.6 km
  • Long Wharf Park - 23 min drive - 24.3 km

Getting around

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

Restaurants

  • ‪Woolford General Store - ‬9 min drive
  • ‪Church Creek Cafe - ‬13 min drive
  • ‪Madison Bay - ‬9 min drive
  • ‪Hudson Manor - ‬37 min drive
  • ‪The Neck District Grill - ‬39 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 at "Endless Summer" Waterfront on the Chesapeake Bay!?

On-site parking is available at the property.

What time is check-in at "Endless Summer" Waterfront on the Chesapeake Bay!?

Check-in begins at 4:00 PM.

What time is check-out at "Endless Summer" Waterfront on the Chesapeake Bay!?

Checkout is at 10:00 AM.

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

Situated in Woolford, this holiday home is 3.9 mi (6.2 km) from Blackwater National Wildlife Refuge and within 12 miles (20 km) of 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 miles (20 km).

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 window
Rating 10 - Excellent. 11 out of 12 reviews
Rating 8 - Good. 0 out of 12 reviews
Rating 6 - Okay. 1 out of 12 reviews
Rating 4 - Poor. 0 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Michael G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everyone had a great time and enjoyed all the amenities of the house and property.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Shana M.

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

6/10 Okay

Teo V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was great in responding to my questions prior check in. House was very clean and indoor pool was nice for the kids. Home description of 2.5 baths but didn't not mentioned master bathroom does not have a door. To use master bath, you would have to kick people in that room out and lock the room door. Otherwise everyone has to wait and use the 1 bath shared on other side. That's was the most inconvenient and annoying part of this house.
Stayed 3 nights in Jul 2026
Response from VrboOwner on 27 July 2026
First let me say we are grateful you chose our wonderful property. You obviously missed the door that closes off the area to the bathroom from the rest of the house. So your description of the master bathroom not having a door is absolutely incorrect. Such a shame you left a subpar review over something that you failed to recognize that was so blatantly obvious. If you would have simply contacted me I could have described to you how close the door the master area. Thanks again
Verified review

10/10 Excellent

Cathy T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was very responsive. All questions answered quickly and accurately. We came in early May, and used the kayaks, and the children played a lot in the indoor pool and had great fun. Some of our party were bird photographers. Every day there were bald eagles, kestrels, a green heron, and several songbirds. The sunrise and sunsets were beautiful. Everyone in our three generation family was able to enjoy being there to help us celebrate my husband’s birthday.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Christopher T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Tuan N.

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

10/10 Excellent

Deb M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We came for a short weekend get-a-way and the Endless Summer certainly provided exactly what we needed. It was peaceful, quiet and absolutely beautiful. The house is huge and would definitely work for a large family gathering. The bedroom layout is really nice for privacy. It was too cold to test the Chesapeake waters, but the indoor pool was such a great option for relaxing.I would say that there is a Keurig machine and a regular drip coffee maker that I didn't see in the write up but were glad to find they were well provisioned coffee wise. And for anything we needed Cambridge was near by and super easy to get to.It was the exact break we needed and we appreciated all Endless Summer had to offer.
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

J H.

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

10/10 Excellent

Dov K.

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

10/10 Excellent

Jennifer H.

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

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
Verified review

10/10 Excellent

Ismael C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We were there for Eagleman 70.3 so we wanted to be close to the area. Even though we were a little bit away from where the race was the location was perfect because we were able to relax as a team and enjoy family style dining. There was plenty of room for all to relax and sit out by the dock when they wanted too. The indoor pool was a hit after being out in the sun all day. I would stay there again even if I’m not coming to Cambridge for a race.
Stayed 4 nights in Jun 2026

About the host

Hosted by Doug Parks

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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