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!

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.

*Waterfront Island Hideaway-A true hidden Gem*

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.

The Daisy in Historic Occoquan (Mins to DC)

Modern & spacious condo in the heart of walkable historic Town of Occoquan. Full kitchen, bath, a comfortable queen bed, work station & free parking. The Town of Occoquan offers unique experiences (kayaking, fishing, birdwatching and shopping) all within walking distance. Excellent dinning choices from award winning restaurants to casual eateries. Mins to I-95, 123, VRE. D.C. (35min); Fort Belvoir (20min); The Pentagon (25min); Quantico (25min); Potomac Mills (10min). Tysons (25min).

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.

Riverfront Retreat-HotTubIDock|Fenced YardINear DC

Escape to the Riverpoint. This unique house embodies the charm of a Swiss chalet A-Frame, complemented by a picturesque boathouse on a serene canal of the Port Tobacco River. You’ll love the Riverpoint’s amenities: Fully-fenced large backyard, Dog friendly, Canoe launch, Italian dual oven range, Hot Tub, Fire Pit, Game Room, Movie room, and more! This retreat promises relaxation & adventure for all families / groups! You may not want to pass it up!

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.

The Cottage on The Farm - Bring Your Horse!

The Cottage at Bit O Berry Farm, LLC is a quaint little cottage on our private horse farm. Wake up to the view of horses out your bedroom window. Relax from the hustle and bustle of life with nature all around. Horses, dogs, cats, pigs and chickens reside here. Historical St Mary's County has great things to offer, from fishing and boating to winery's, fresh markets and much more!

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.