Holiday rentals in Charlotte Hall

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Top-rated holiday rentals in Charlotte Hall

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Top guest favourite
A serene dock extends over calm waters, surrounded by lush greenery. A small orange kayak is secured nearby. In the background, a custom waterfront home is nestled among tall trees, providing a natural and tranquil setting.
Home in Mechanicsville
5 out of 5 average rating, 91 reviews

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

Guest favourite
The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.
Cabin in Lusby
4.91 out of 5 average rating, 233 reviews

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 --

Top guest favourite
Farm stay in Huntingtown
5 out of 5 average rating, 87 reviews

Luxury Farmette -Private & Secluded-1hr to DC

Plan your tranquil getaway to the countryside and escape to a luxury dream farmhouse. Located on 5 acres, the fully renovated home offers peace in a quiet, private location. Guests have access to a pool and outdoor shower, fire pit, a covered grilling area and a playground for children. The home is located approximately 1hr from Washington DC and is the perfect place for a retreat, family vacation and everything in between! Plenty of parking available for those traveling with boat/camper/RV.

Top guest favourite
Apartment in Mechanicsville
4.99 out of 5 average rating, 94 reviews

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.

Top guest favourite
A cozy sitting area features a comfortable blue sofa adorned with cushions. Large glass doors provide access to the outdoor space, complemented by colorful curtains. A small dining table and chairs are visible outside, framed by a patterned area rug on the wooden floor.
Guest suite in La Plata
4.89 out of 5 average rating, 290 reviews

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.

Top guest favourite
A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.
Home in Leonardtown
4.99 out of 5 average rating, 108 reviews

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!

Guest favourite
Guest house in Hague
5 out of 5 average rating, 8 reviews

Bell House

Two-bedroom guesthouse with deck overlooking the Lower Machodic Creek (Coles Point, Hague VA) the perfect setting for enjoying sunrise and sunset. Shared property, but the second floor guesthouse is all yours. The first floor is a garage we use for storage. Salt water lap pool, 100 feet of beach on Lower Machodic Creek with expansive views of the Potomac River, kayaks, private dock, and 20 acres to explore. Great for a family vacation, couples getaway, girls weekend, you name it!

Superhost
The exterior of a two-story brick house is presented, framed by well-maintained green lawns and colorful landscaping. A clear sky highlights the structure, while a walkway leads up to the front door, surrounded by mature trees and shrubs adding to the serene atmosphere.
Home in Mechanicsville
4.64 out of 5 average rating, 11 reviews

Perfect Maryland Get Away

Forget your worries in this spacious and serene space. The home is located in a small quiet community. Being the last house on the Col-de-sac, you are surrounded by private area and 2 acres of beautiful woodlands! The house is a spilt foyer, the top half being where you would stay and the bottom half being the property managers seperate area. The top level has 3 spacious bedrooms, 2 bathrooms, living room, full size kitchen and dining area and a washer and dryer too.

Top guest favourite
Guest house in Brandywine
5 out of 5 average rating, 53 reviews

Quiet cottage in the woods. King-bed suite.

Take it easy at this unique and tranquil getaway. Open floor plan with all the modern conveniences. King size bed, with space for an additional queen size air mattress. Washer, dryer, shower/bathtub. Note, there is no smoking or vaping allowed inside the Cottage, and absolutely no "4/20" products allowed on the property. Two night minimum for all reservations, and due to documented medical allergy concerns we are unable to host pets/animals of any kind.

Top guest favourite
A gravel driveway leads through a landscaped yard lined with trees, leading to a two-story house in the background. The vibrant green grass is complemented by the clear blue sky above, creating a serene and inviting outdoor setting.
Guest suite in Bryantown
4.96 out of 5 average rating, 72 reviews

Beautiful countryside retreat within reach of DC

A recently renovated, peaceful getaway-from-it-all , yet close enough to places of interest. Enjoy the retreat like setting, quiet mornings with coffee, deer and birds. Then head out to DC, Annapolis, Baltimore or just unplug in this peaceful and secluded one bedroom with full kitchen.

Guest favourite
A dining area features a round wooden table surrounded by two black chairs, with a floral centerpiece. Off to one side, a wooden cabinet with glass doors holds various items. The kitchen area includes dark countertops and a sink, illuminated by overhead lighting.
Flat in Prince Frederick
4.96 out of 5 average rating, 23 reviews

Cozy nest for one or two

Keep it simple at this peaceful and centrally-located place.this one bedroom apartment is located centrally between Prince Frederick and Solomon’s on the main highway easy accessible.

Guest favourite
A spacious living area is framed by tall windows that provide views of the outdoor greenery. The high wooden ceiling features exposed beams, and natural light enhances the inviting atmosphere. A cozy sofa arrangement is visible, along with a patterned area rug on the wooden floor.
Home in Huntingtown
4.95 out of 5 average rating, 73 reviews

House near Patuxent River

Take it easy at this unique and tranquil getaway. Quiet and peaceful neighborhood. Water privilaged community. Less than an hour from Annapolis, DC, and Solomons Island.

Popular amenities for Charlotte Hall holiday rentals