Holiday rentals in Chaptico

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 --

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

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!

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

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.

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

Summer Perfect, Water Front A-frame on Winery

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.

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.