Holiday rentals in Delmarva Peninsula

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.

Strathmere Beachfront House

Luxury Beachfront Home Welcome to the Strathmere Beachfront home. A beautifully designed, luxury vacation home, where every detail is set to provide a you dream getaway. When you enter the home, you will be immediately taken by the panoramic ocean views from Atlantic City to Avalon. This well-appointed home, from chef’s kitchen Wolf and Sub-Zero appliances, to the Serena and Lily bedding, to the coastal / modern furniture, provides you and your family a welcoming environment. Treat yourself!

SandyPaws Cottage at Big Stone Beach on the DE bay

This is a newer cottage on the Delaware Bay near Milford, DE, only 25 minutes to Rehoboth Beach and the Atlantic Ocean. Sleeps 4, 2 bdr, 1 bath, a double and a queen bed. Large sunny great room with tv and DISH satellite. There is over 500 sq feet of deck space overlooking the bay and the freshwater marsh managed by the Nature Conservancy. Watch sunrise over the bay and sunset over the beautiful marsh filled with many species of birds. Dogs must be walked on a leash and do-do picked up!

Private Country Beach Retreat

Welcome to Mason Jar Retreats Beach Home. Our home is a private beachfront property with the best of both country and beach living. Located on 6 acres on a private road with only a few steps to take to your private oasis on the Chesapeake Bay. Enjoy sunsets from the beautiful porches while taking in the natural surroundings. Our home is only three miles from a vineyard and winery and 20 minutes to Cape Charles with lots of shopping and dining in a quaint beach town. *LGBTQ+Friendly Home

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 :)

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

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”).

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU

BEFORE BOOKING: Pool will be open 4/05/26 NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your reservation are allowed on the property. Fully restored top to bottom 1920s farm house. Every bedroom has its own full bathroom Full laundry room with extra refrigerator RH furniture All bedding/towels/paper towels/toilet paper/body wash/shampoo/conditioner/spices/laundry detergent included;Total turn key

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning 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).