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"Endless Summer" Waterfront on the Chesapeake Bay!

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

A wooden pier leading to a house with a deck and outdoor seating area, surrounded by trees and a body of water.
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.
A covered deck with Adirondack chairs, a glass door leading to a grassy area, and a small building with shutters.
A modern indoor swimming pool with clear water, surrounded by white walls and large windows.
A living room with a sectional sofa, a coffee table, and a small side table with a plant. There is a kitchen area with wooden cabinets and a dining area visible in the background.

Reviews

9.8 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
    ‪8 min drive‬
  • Place, Harriet Tubman Underground Railroad National Historical Park
    ‪19 min drive‬
  • Place, Northern Chesapeake Bay
    ‪22 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪59 min drive‬

Room options

About the neighborhood

Woolford

This vacation home is located 3.9 mi (6.2 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.
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What's nearby

  • Blackwater National Wildlife Refuge - 8 min drive - 4.5 miles
  • Harriet Tubman Underground Railroad National Historical Park - 19 min drive - 11.9 miles
  • Northern Chesapeake Bay - 22 min drive - 13.5 miles
  • Harriet Tubman Museum and Educational Center - 23 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
  • ‪The Neck District Grill - ‬39 min drive
  • ‪Soft & Salty Seafood - ‬47 min drive
  • ‪Hudson Manor - ‬37 min drive
  • ‪J-Bird's Church Creek Cafe - ‬13 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.

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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
  • Bed sheets 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

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 24

Check-out

Check-out before 10:00 AM

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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 24

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. Blackwater National Wildlife Refuge is also within a driving distance of 3.9 mi.

Will I be able to park at "Endless Summer" Waterfront on the Chesapeake Bay!?

No, this vacation home doesn't offer parking.

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.

What amenities will couples enjoy at "Endless Summer" Waterfront on the Chesapeake Bay!?

There are many amenities for couples at this vacation home, including a private pool, a private pool in some house, as well as an indoor pool.

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

No, but guests can enjoy a heated pool at this vacation home.

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.

Does "Endless Summer" Waterfront on the Chesapeake Bay! have connecting rooms available?

No, there aren't connecting guestrooms 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.

Can I book a room with a balcony at "Endless Summer" Waterfront on the Chesapeake Bay!?

Yes, every house at "Endless Summer" Waterfront on the Chesapeake Bay! comes with a patio.

"Endless Summer" Waterfront on the Chesapeake Bay! Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 13 out of 14 reviews
Rating 8 - Good. 0 out of 14 reviews
Rating 6 - Okay. 1 out of 14 reviews
Rating 4 - Poor. 0 out of 14 reviews
Rating 2 - Terrible. 0 out of 14 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

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

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

10/10 Excellent

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

10/10 Excellent

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

6/10 Okay

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
Verified review

10/10 Excellent

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

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

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

10/10 Excellent

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

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

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

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had the best time at Endless Summer! Great house and lovely property. The beds were comfortable and the pool was wonderful. We saw turtles, a variety of birds including eagles, deer and rabbits each morning while drinking coffee by the water. Lovely pier and we enjoyed kayaking, crabbing and fishing. Would have been helpful to have a bit more kitchen items (i.e. trash bags, paper products, cleaning items) at least to start off. If you plan to stay and cook in; consider bringing those types of items. Would definitely love to visit this property again in the near future.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

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