Vacation rentals in Cobb Island

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!

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!

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

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!

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

Rest & Recharge, A-frame Cabin on Winery Grounds

This serene cabin is on the Ingleside Vineyard's property. Have a glass or two of wine and walk around the vineyards and then retreat to your own private a-frame cabin oasis. A beautiful view of the Roxsbury Estate where abundant wildlife can be viewed all around the property and the pond is stocked and ready to be fished. Within driving distance to wineries, Stratford Hall, George Washington & James Monroe's birthplace, Westmoreland State Park, and the beach town of Colonial Beach.

Colonial Beach Retreat • Private Beach Access

Escape to your own private slice of Colonial Beach. This entire 3-bedroom, 2-bath home comfortably sleeps up to 6 and offers rare private beach access just steps away. Enjoy mornings with coffee on the deck, evenings around the firepit, and peaceful sunsets with ducks and swans drifting by. Just a short drive (under 6 miles) to the boardwalk, shops, and dining. Relax, recharge, and stay awhile. Please read the "Other details to note section" prior to booking your stay. Thank you!

Waterfront Cottage in Colonial Beach at Placid Bay

Luxury Cottage with private water views full of natural wildlife. You will love the open floor plan with a chef's kitchen stocked with All the essentials including beverages and coffee. Sleep late with private bedrooms that include luxurious bedding Enjoy the expansive outdoor space complete with Patio, Pergola, Fire Pit, and large deck with outdoor kitchen. Walk down to the 28ft foot dock where you can fish, relax in the sun or take the Kayaks for a ride Close to DC and NOVA

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. However, the space is small and it is really a studio apartment as I think the pictures make evident.

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

Sunset Point-Waterfront home&shared pier for boat!

Perfect escape with waterfront views and pier. Calling all water and boat lovers! The house is fully outfitted with all amenities you will need. Located on the point and only a quick walk to Dockside restaurant, Colonial Beach Yacht center, town boat ramp, beach and more! Pier access for fishing, swimming or you can bring your boat! Rent a golf cart to travel around town. You will fall in love with the welcoming, fun, quiet little town!

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Welcome to Sunset View Cottage. A spacious and bright two-level waterfront home with a private dock and beach access in Leonardtown, MD. Enjoy swimming off the dock and beach in the Potomac River. Full western views across the widest part of the river make for unbelievable sunsets. Your ideal family vacation, couples getaway, or work-from-home retreat just 90 minutes outside DC. Visit us on IG @sunsetviewcottage