Chesapeake Bay Retreat offers a tranquil escape on the Bay with stunning sunsets and ocean liner views. Guests will enjoy a heated pool, kayaking, grilling, bonfires, and traditional Chesapeake activities like fishing & crabbing. The 22 ½ acre estate offers wildlife featuring deer, turkeys, and eagles. Comfortable accommodations for 16+ include TV rooms and private bathrooms. Nearby restaurants, and a public boat launch enhance the experience. The retreat delivers endless relaxation & adventure The space **UNDER NEW MANAGEMENT**
22 1/2 acre Chesapeake Bay estate
475' shoreline
Heated Pool
Outdoor Bar
Paved driveway
New furniture indoor and out Guest access The entire property is for you use and enjoyment Other things to note -Spectacular Sunsets and Scenic Views
Nestled along the serene shores of the Chesapeake Bay, this Retreat offers an idyllic escape from the hustle and bustle of everyday life. The picturesque waterfront property promises an unforgettable experience with its stunning amenities and breathtaking views.
One of the retreat's most enticing features is its amazing westerly sunsets, providing a spectacular display of colors over the horizon each evening.
Guests will also enjoy breathtaking views of the grand ocean liners as they navigate the waters of the Chesapeake Bay, creating a perfect backdrop for relaxation and reflection.
You can enjoy all from scenic balcony or from the newly installed dock.
-Endless Activities and Amenities
Chesapeake Bay Retreat is a haven for fun and adventure, offering a plethora of activities and amenities to suit every preference, kids and adults alike:
** Heated Swimming Pool: Dive into the refreshing waters of the pool, ideal for both relaxation and exercise. ** Kayaks: Explore the bay at your leisure with the kayaks provided, offering a unique opportunity to connect with nature.
** Grilling and Bonfires: Savor delicious meals grilled to perfection and unwind by the warmth of a crackling bonfire under the stars.
** Fishing & Crabbing: Engage in the traditional Chesapeake Bay pastime of fishing and crabbing, promising both excitement and a delicious reward. All can be experienced from the 125' long pier and new dock.
** Wildlife & Sightseeing: Engage nature’s serenity, just in the front yard, of this 22 ½ acre estate. You will be able to see deer (whitetail and the elusive Sika), turkeys, eagles, and so many more.
-Comfortable Guesthouse Accommodations
The guesthouse at the retreat is designed for comfort and convenience, providing a cozy sanctuary for up to six guests.
It includes a TV room perfect for relaxation and entertainment, along with a private bathroom for added comfort.
-Your Perfect Getaway Awaits
Chesapeake Bay Retreat is more than just a vacation spot—it's a destination where tranquility and adventure coexist harmoniously. Whether you're seeking solitude or excitement, this waterfront paradise is sure to deliver an unforgettable experience making all of your wonderful memories even more nostalgic.
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The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds, gather used towels and store extra beds
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Kindly collect all trash and deposit into dumpster located on driveway
Close propane tank valve
Please set thermostats:
Heating: 60
A/C: 78
Close all umbrellas and lay down on ground
Return all (6) pool lights to Main House, 1st floor TV stand
Failure to complete these may result in a negative review from the host.
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
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Cambridge
Cambridge is home to this holiday home. Spocott Windmill and Choptank River Lighthouse are local landmarks, and some of the area's activities can be experienced at Knapp's Narrows Marina & Inn and Tilghman Island Marina. Richardson Maritime Museum and Dorchester Arts Center are also worth visiting.
Harriet Tubman Museum and Educational Center - 26 min drive - 26.9 km
Choptank River Lighthouse - 27 min drive - 27.6 km
Gerry Boyle Park at Great Marsh - 27 min drive - 26.5 km
Getting around
Cambridge Station - 33 min drive
Easton, MD (ESN-Easton - Newnam) - 52 min drive
Restaurants
Madison Bay - 43 min drive
Soft & Salty Seafood - 10 min walk
Palm Beach Willies - 51 min drive
Millie's at Madison Bay - 43 min drive
Maryland Blue - 43 min drive
Frequently asked questions
Does Chesapeake Bay Retreat have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at Chesapeake Bay Retreat?
As of 6 May 2026, prices found for a 1-night stay for 2 adults at Chesapeake Bay Retreat on 9 May 2026 start from NZ$1,486, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Chesapeake Bay Retreat pet-friendly?
Yes, this property allows pets (limit 2 total).
How much is parking at Chesapeake Bay Retreat?
On-site parking is available at the property.
What time is check-in at Chesapeake Bay Retreat?
Check-in begins at 4:00 PM.
What time is check-out at Chesapeake Bay Retreat?
Checkout is at 10:00 AM.
Where is Chesapeake Bay Retreat located?
Situated in Cambridge, this holiday home is within 3 miles (5 km) of Chesapeake Bay, Northern Chesapeake Bay and Ragged Island. Spocott Windmill is 7.4 mi (12 km) away.