Family-Friendly rentals near Chesapeake Bay

Osprey's roost: Spring and summer 2025

Hidden treasure! Come join the osprey along the Potomac River in the Northern Neck of Virginia! This 4 bedroom/3 bath custom home is at the end of a quiet lane and sits on a point of land between the Potomac River and Blackbeard’s Pond, making for magnificent river views from sunrise to sunset. Enjoy swimming, canoeing, Bocce on the lawn, barbecue on the deck! Osprey’s Roost is the perfect retreat to rest and recharge, ideal for a romantic week away, a girls’ weekend or a family gathering!

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

A "True" Chesapeake Bay Waterfront Experience!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!

"No Bad Days" in this Fabulous Beachhouse w/ Dock!

You'll have "No Bad Days" in this beautiful beachfront home on the Rappahannock River with 123' of private beach and private dock with jetski lift. This stylish, comfortable home is well equipped with many inside and outdoor amenities. Watch sunset at the outdoor firepit table or choose the indoor fireplace in colder months. High speed internet and Smart TVs keep you connected while you kayak, bike, fish and enjoy river living at its finest. The town of Deltaville is 2 miles away.

Urban Cottage,MD minutes from DC/National Harbor

Come and enjoy our spacious detached cottage,lounge on your private back deck overlooking private parkland forests. A real urban escape in an excellent location! Just a few blocks away from the MGM Resort / Casino, National Harbor, and shopping. Across the river from historic Alexandria and 10-minutes from Washington,DC. Great for a solo adventure,couples,and friends (up to 4 guests). Enjoy the seasonal steam house and personal wood-burning stove if you book in the cold months.

Sea Dreamer

Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

Walk to famous Tiki Bar on Solomons Island!

Cute studio apartment on charming Solomons Island. Walking distance to restaurants, live music, boat and kayak rentals. The kitchen has a full sized refrigerator, microwave, toaster, two burner hot plate and coffee maker. We provide all bedding and bath towels for two people. Enjoy your coffee ( provided) or wine on the deck in the fenced in side yard. One well-behaved pet is welcome. Please make sure you pay the pet fee.

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300-foot private beach. The year-round property has a pier, and in-ground pool (May-October) with amazing river views. Also hosts weddings+events up to 100 guests (additional event fee applies).

Cove Point Beach Cabin

My place is close to shopping, restaurants and dining in Lusby and Solomons Island, the Chesapeake Bay, and family-friendly activities. You’ll love my place because of the comfy beds, the coziness, and the views. My place is good for couples, solo adventurers, business travelers, and families (with kids). No pets allowed.