Holiday rentals in Charles County

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!

Patuxent River View

🏡Stay at this peaceful, amenity‑rich guest house near North Beach, Chesapeake Beach, and Herrington Harbour, with quick access to Washington, DC, Baltimore, and Annapolis. Enjoy a fully stocked kitchen, coffee, fast WiFi, a seasonal pool, and a shaded gazebo designed for comfort and convenience. Perfect for wedding weekends, family visits, work trips, and quiet coastal getaways, this cozy home base makes it easy to relax, cook, stream, and recharge between festivities and exploring the area.

Barnyard Retreat

We are BACK After a 2 year hiatus!! We cannot wait to see all of our wonderful guests again! Beautiful 750 sq. ft. in-law apartment set up in a very efficient setting with open living space and Jack-n-Jill bathroom. Space is very open with cathedral ceilings and sky-lighting. Apartment has it's own separate entrance and dedicated parking space. The apartment has fast, secure wi-fi and is set-up perfectly for traveling professionals! Please see additional info within our house rules section.

Beautiful Rural Suite near Washington, D.C.

Enjoy a rural environment only 50 minutes outside of Washington, D.C., and 45 minutes away from Andrew's Air Force Base. Located in a quiet wooded neighborhood with horses, goats, ducks, and more this property allows children space to run and play. Stores are less than 10 minutes down the road. This is a perfect little haven, fully equipped with a kitchen and laundry facilities. Parking is available for boats and trailers. Please Note: Sunday check-in is at 4pm, unless requested otherwise.

River Rock - Walk to Beach

Relax with the whole family at this peaceful place to stay. This modern home offers a fully equipped kitchen and stair-free, comfortable living spaces. The house features a fenced backyard with a gas grill, pellet smoker, and plenty of outdoor seating. Amenities include free coffee, WiFi, and smart TVs, making this home perfect for a fun and relaxing vacation. The private, neighborhood beach is a 5 minute walk from the house and leashed dogs are allowed on the beach year-round.

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.

Bayside Bungalow

This beach cottage is on the point with view of Monroe Bay from the backyard. Walking distance to breweries and restaurants. Only 3 blocks from the beach! Open floor plan with a kitchen, dining room, living room, and office/laundry room. There is a dedicated working from home space that includes a mouse, monitor, and keyboard. The backyard is fully fenced with a patio and table and chairs. The living room has a smart tv that includes Apple TV & a sound bar.

The Lake Oasis Retreat *cozy, serene, relaxing*

Escape to The Lovers’ Lake Oasis, a cozy four-season retreat designed for romance and relaxation. Soak in the hot tub under soft twilight lighting, take in peaceful Placid Lake views, or unwind in the secluded backyard. On warmer days, walk five minutes to the dock and launch a kayak. For a special touch, add our romantic decor package with roses, candles, chocolates, and bubbly ($320) to enjoy while stargazing from the hot tub. Serenity awaits. 🍾🥂❣️

The Farmhouse in Historic Occoquan Close to D.C.

This private home is spacious, bright, open, and welcoming. The second floor has 2 master suite bedrooms. One bedroom with a king bed, jacuzzi tub and shower plus a queen bed with a tub. The living room has convertible sofas and air mattresses. The home sleeps up to 10 and has lots of storage. Perfect for families and groups, but no parties please! We have a strict NO pets rule because one of the owners has life threatening allergies.

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.

River Refresh - Waterfront with Spa on Placid Bay

Nestled along the gentle curves of Mattox Creek, River Refresh stands as a serene sanctuary, a perfect retreat from the hustle and bustle of everyday life. The house, adorned with a soft palette of earthy tones, seamlessly blends into the surrounding natural beauty, creating an atmosphere of peace and relaxation.