Chesapeake Dream (Eastern Shore)

Chesapeake Dream is a renovated waterfront farmhouse on 5.6 private acres, offering sweeping Chesapeake Bay views and a true Eastern Shore escape. Designed for guests who want space, scenery, and direct access to the water, this vacation rental blends classic farmhouse character with modern comfort in a setting that feels open, peaceful, and deeply connected to nature. From sunrise to sunset, the bay becomes part of your stay, visible from throughout the home and across the property.

This Chesapeake Bay vacation rental comfortably hosts a maximum of 12 guests, including children and infants, making it ideal for family vacations and friend group getaways that value shared experiences without overcrowding. The generous layout allows everyone to spread out while still coming together easily in the home’s main living areas and outdoor spaces.

For boaters and water lovers, Chesapeake Dream offers an exceptional waterfront experience. With private shoreline access and a dock on site, guests are welcome to bring their own boat and take advantage of nearby public boat ramps. Days can be spent boating across the bay, fishing from the dock, crabbing along the water’s edge, or kayaking directly from the property using the two provided kayaks with life jackets during the season.

Outdoor enthusiasts will find this Eastern Shore getaway especially rewarding. The property is well suited for fishing, crabbing, deer and duck hunting, and bird watching, either directly on site or through nearby guides and excursions. Quiet mornings with coffee on the porch, afternoons watching wildlife through the telescope, and evenings unwinding in the hammock or swing create a natural rhythm that makes it easy to disconnect from daily routines.

The outdoor living spaces are designed to make the most of the bay views and fresh air. A large screened porch and an open air balcony provide comfortable seating for everything from slow mornings to long conversations at sunset. As evening settles in, gather around the bayside wood burning fire pit or the outdoor fireplace, with firewood provided, and take in the changing colors of the sky reflected across the water.

From late spring through summer, the heated swimming pool becomes a favorite gathering spot. Available from May through September, the pool offers a refreshing escape on warm days, with optional heating available for added comfort. A seasonal pool house bathroom with a shower allows guests to move easily between swimming, lounging, and outdoor dining without tracking water through the home.

Entertaining is seamless thanks to the outdoor kitchen, which includes a gas BBQ grill and refrigerator. Prepare fresh meals, grill seafood, and serve drinks poolside while enjoying uninterrupted Chesapeake Bay views. This setup is ideal for summer cookouts, celebrations, and relaxed evenings spent outdoors with family and friends.

Inside, the home is fully air conditioned and heated with a central air system and split units to ensure year round comfort. The living spaces are welcoming and thoughtfully equipped with a gas fireplace for cooler evenings, high speed Wi Fi for work or streaming, and a Sonos Bluetooth sound system that allows you to enjoy music throughout the house.

The fully stocked kitchen supports everything from casual breakfasts to full family dinners. A farmhouse sink, large island with stool seating, and stainless steel appliances make cooking both functional and enjoyable. Guests have access to a gas stove and oven, dishwasher, microwave, air fryer, toaster, slow cooker, blender, and a mini fridge for drinks. A coffee pot and Keurig are stocked with coffee pods and grounds, while cooking and baking basics, tableware, cutlery, basic spices, and grilling utensils are all provided.

Sleeping accommodations are arranged to comfortably support groups of up to 12 guests. The second floor features two queen bedrooms along with a private master suite offering a king bed, TV, soaking tub, shower, and ample storage. The third floor includes an additional queen bedroom and a loft style kids bedroom with one double bed and three twin beds. A large sofa in the first floor living room provides flexible lounging space, and two pack n plays are available for younger guests.

Every detail has been considered to make your stay easy and comfortable. Linens, pillows, towels, shampoo, conditioner, body wash, laundry detergent, dishwasher detergent, and dish soap are all provided. Guests will also find ceiling fans, a washer and dryer, hair dryer, first aid kit, basic cleaning supplies, and ample clothing storage throughout the home.

Chesapeake Dream offers driveway parking for up to ten vehicles and provides guest access to the dock, bay, and seasonal swimming pool. While boat lifts are not available for guest use, the dock is ready for fishing, crabbing, and easy access to the water. With nearby boat rentals, historical landmarks, hiking trails, golf courses, and charming towns to explore, this Eastern Shore vacation rental is perfectly positioned for both adventure and downtime.

Whether you are planning a family vacation, a friends’ retreat, or a seasonal escape focused on the outdoors, Chesapeake Dream delivers space, scenery, and Chesapeake Bay access in one unforgettable setting. This waterfront farmhouse invites you to enjoy the land, the water, and the simple pleasure of being together in a place designed for meaningful moments and lasting memories.