Holiday houses in Issue

The River House, a Wicomico Beach Retreat

Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The acre+ plot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos, plus a fabulous sleeping loft for the kids!

Location · Family · Beach

Waterfront 4-BR home w/ hot tub & charging station

Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

Family · Location · Comfort

Lovely 5 bedroom home, TVs in all bedrooms.

Escape to this spacious and inviting 5 bedroom home, perfectly situated in a quiet neighborhood just a short walk from the beach. Designed for comfort and convenience, the well appointed kitchen is ready for home-cooked meals. A premium propane grill is also provided for our guests. Each bedroom is equipped with its own TV ensuring relaxation for all. There is a large fenced backyard with a fire pit perfect for relaxing under the stars. Pets are welcome. The home is also handicapped accessible.

Family · Location · Comfort

Happy Hour~Private dock, amazing sunsets, peaceful

Perfect for a private, scenic romantic get away or for a group of 4. Open for short- and long-stays. ‘Happy Hour’ is a uniquely furnished 2 bd/2 ba riverfront cottage at Cobb Island, Md, where you can chill to your heart’s content with panoramic views & sunsets on the Potomac River. Drop anchor! 2 bikes. Great fishing. 2 TVs, Wi-Fi, fully-equipped kitchen, W/D, deck, charming 1,100 sq.ft., 40s home. Enjoy the serenity. 3-ni. minimum reservation. Sleeps 4 max. No partiers. Unforgettable home!

Value · Location · Outdoor spaces

Crab Shack in Town walk to beach and restaurants

Centrally located in town and blocks from amenities, Crab Shack is a pet-free home that was renovated in 2022 and offers a place to rest, relax, and enjoy the cool breezes from Monroe Bay. Enjoy outdoor living with a spacious patio and dine outdoors in your own screened-in crab shack. Indoors, enjoy 3 spacious BR's and 2 full BA's, stocked kitchen, and inviting living and dining rooms. Walk just a few blocks to shops, restaurants, breweries, and the beachfront and enjoy expansive water views

Location · Value · Hospitality

The Observatory on Rose Manor

The Observatory on Rose Manor is your own private space. It’s 2 blocks from the heart of downtown & beach. We are the golf cart capital of Virginia; rent one when you're in town. We are just over an hour south of DC. Many historic sights, town events & live music here. This small town will take you back in time. This rental is on the grounds of Rose Manor. Rose Manor was built in 1896; it operated as the New Willard Hotel for over 50 years. Come relax on the porch & enjoy the water view.

Family · Location · Bathroom

*Where Eagles Soar* Peaceful Waterfront Retreat.

YOUR WATERFRONT OASIS AWAITS! If you are looking for a true getaway, look no further. Tucked away on a small, peaceful island, this hidden gem is uniquely surrounded by 3 bodies of water: The Potomac River, the Wicomico River, and Neale Sound. This quiet island oasis offers the perfect place to step away from the busy world! This cottage is incredibly special to us. For four generations, it has been a sanctuary for our family-filled with love, laughter, and countless memories.

Family · Location · Kitchen

Riverview on the Potomac

Relax and unwind at 'Riverview on the Potomac'. • 5 mins drive to pier and beach access • 15 min to Ingleside Vineyards • Fully equipped backyard with outdoor kitchen, bar, hammock swings, fire pits, and plenty of seating to enjoy with your family and friends • Large jet tub in the master bathroom • Beach necessities (toys, wagon, chairs, umbrella) • Family Friendly: high chair, pack-n-play, baby gate, and board games • Two dedicated workspaces for days you need to work

Value · Location · Checkout

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. Childlren under the age of 12 and pets are not allowed.

Location · Value · Walkability

‘Pipe Dream’ - 3BD/2.5BTH - Awesome water view!

'Pipe Dream' is a unique two-story home in Colonial Beach, perfect for multiple families. This 3BD/2.5BTH house faces Monroe Bay, offering stunning sunset views of the water from both the first and second-story porches. The first floor includes a living room, kitchen, dining area, and the main bedroom. The second floor features a spacious recreation room, giving adults and children their own areas to relax and enjoy.

Location · Value · Indoor spaces

Gatton Farm Guesthouse

Gatton Farm Guesthouse is a two bedroom, one bathroom second floor dwelling above a detached garage located in picturesque Newburg, Maryland. Being on 15 acres and only one thousand feet from the Potomac River, guests will enjoy views of Canadian geese, wild turkeys, bald eagles and white tail deer. Gatton Farm is also considered a historical site as it was once the residence of famous guitarist Danny Gatton.

Location · Family · Bathroom

Peaceful waterfront home, 1-hour from DC

Beautiful home with stunning sunset views on the lower Potomac River. Home features a private pier, fire pit, theater room, and play area for kids! Only 1 hour from DC, 90 mins from Richmond. Easily accessible from anywhere in the DMV area. Full kitchen, and large screened in back porch. This is a vacation home-come true.

Value · Location · Walkability