Waterfront holiday rentals in Delmarva Peninsula

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”). And be sure to visit our sister property, White Point Cottage!

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Historic Rousby Hall, Waterfront, Pool, Beach

*Summer dates released mid-January* Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

Hutch's Bluff - Waterfront near Williamsburg

Charming riverfront A-Frame home on 2 acres overlooking the Chickahominy River. Completely updated interior, including all furnishings and appliances. Wake in a King bed loft space with a majestic view of the river, or choose one of the two Queen bedrooms below. First floor all tile bathroom with a walk in shower. Stainless appliances and granite countertops. Bring your fishing gear, relax at the end of the pier, or enjoy the views from the large deck and fire pit.

Waterfront-View of Bay from your Bed- Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.