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Chesapeake Bay Retreat

Photo gallery for Chesapeake Bay Retreat

A deck with two lounge chairs and a striped umbrella, overlooking a body of water. - Chesapeake Bay Retreat (Cambridge)
An aerial view of a coastal property with a large house, a swimming pool, and a dock extending into the water. - Chesapeake Bay Retreat (Cambridge)
A room with a large window, a gray armchair with a blue pillow, a wooden dresser, and a patterned rug. - Chesapeake Bay Retreat (Cambridge)
A pool with a surrounding deck, a covered outdoor seating area, and a building with a red roof. - Chesapeake Bay Retreat (Cambridge)
A spacious room with a large window offering a view of the sea, a wooden floor, and a white door. - Chesapeake Bay Retreat (Cambridge)
A firepit, a garden and a playground are just a few of the amenities provided at Chesapeake Bay Retreat. Stay connected with free in-room WiFi, with a speed of 500+ Mbps (good for 6+ people or 10+ devices), and guests can find other amenities such as laundry facilities.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

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About this property

Chesapeake Bay Retreat

  • 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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About the area

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. Visit our Cambridge travel guide
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Map
Cambridge, MD

What's nearby

  • A large suspension bridge over a calm body of water with a sunset in the background.
    Northern Chesapeake Bay
    6 min drive - 2.2 miles
  • A lighthouse on a wooden pier with a boat docked nearby.
    Choptank River Lighthouse
    27 min drive - 17.2 miles
  • Ragged Island
    9 min drive - 3.2 miles
  • Spocott Windmill
    15 min drive - 9.0 miles
  • Gerry Boyle Park at Great Marsh
    27 min drive - 16.7 miles

Getting around

  • Cambridge Station
    33 min drive
  • Easton, MD (ESN-Easton - Newnam)
    52 min drive

Restaurants

  • Madison Bay
    43 min drive
  • The Neck District Grill
    11 min drive
  • Soft & Salty Seafood
    10 min walk
  • Hudson Manor
    15 min drive
  • Millie's at Madison Bay
    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.

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.

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Reviews

Chesapeake Bay Retreat Reviews

10

Exceptional

10

Cleanliness

9.4

Location
Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was such a great property 22 acres beautiful views. The pool was fantastic. The pier was great fishing. We had great quality family time and loved that there was an outdoor apartment that could sleep at least four people. That was pleasantly surprising as I thought all the bedrooms were in the main house. The host was really kind and on top of everything. Very accommodating. I’ll be back for sure!!! Mosquitos were my only annoyance. Bring lots of spray!
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location is beautiful, house was clean and comfortably accommodated 8 adults, 4 children and dog. We thoroughly enjoyed the pool, deck and dock. We even caught a few crabs! Ernest was very accessible via text to answer questions. We would definitely return!
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was perfect for our long weekend near Cambridge for the Ironman competition. Ernest was amazing and always responded to any questions in a timely manner.
Stayed 3 nights in Jun 2026