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Compare 125 Vacation Homes in Charlotte Hall with updated reviews, rates, and availability.

The driveway allows for plenty of parking for guests!

"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."

Large front deck with lights and private fenced yard

"The overall cleanliness of the cottage was a 10/10. Everything was neat and clean. Other than snow not being shoveled and the steps being slippery I have no complaints. "

Welcome to Hawthorn House, centrally located and just 1 block from main street!

"This house has been beautifully restored and was the perfect getaway for 2 couples & 2 kids under 5. The rooms are spacious, the front porch & back deck are great outdoor spaces, and the kids loved running around the backyard and hanging in the hammocks. The linens were soft & clean & plentiful, and we had everything we needed in the kitchen & for using the grill. Also, the host was very responsive & accommodating. We literally couldn’t ask for more in a vacation rental house. Thank you for...

View from back deck looking onto the private dock and creek

"This was a great stay. Very nice, comfortable, great layout, convenient location. I highly recommend. "

"Classic cottage, very clean and well-supplied. Comfy bed in main bedroom! Beautiful property on the river - quiet and peaceful. Lovely sitting areas both inside and out. Restorative!"

Sunroom off the kitchen and living room with a magnificent view of the Chesapeake Bay

"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "

"This house was just what we needed for our business associates. "

"Quite and friendly neighbors "

Warm and Homey with Beautiful River Front Views

"Awesome property/location/amenities/host! We enjoyed every nano-second of our stay, and that is due to the host/hostess and the property they maintain and provide in the best way possible. We couldn't have wished for a better experience and hope to visit again and again. If you are planning to visit Cobb Island, this is the property you want to be at. Every inquiry before arrival was responded to promptly, and upon arrival, we were amazed at how clean and well addressed all our needs were...

Sit on the patio and enjoy your coffee in the morning.

"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "

Lusby Vacation Rental | 4BR | 3BA | 3,720 Sq Ft | Stairs Required

"Our family was looking for a place to gather to visit our Aunt who lives in the area. Six of us stayed at the Waterfront Lusby home and hosted a dinner for our Aunt and cousins. There was plenty of space for our gathering in addition to the comfortable accommodations for our weekend stay. The neighbors were very friendly and welcoming."

"This property is outstanding! Absolutely spotless and host super to work with. Great neighborhood, easy walking and our dogs loved it too!"

"The host had the house under renovation and caused us to have to find a hotel 1.5 hours away from the event we were coming to"

"We were here for Thanksgiving, but were thinking the whole time that this would be a great spot in warmer weather. With the water access and spacious accommodations it would be a great basecamp."

Leonardtown Vacation Rental | 4BR | 4BA | 6,500 Sq Ft | Steps Required

"We had a wonderful time. My husband spent the days crabbing from the pier, my brother fishing from the pier. We all went out kayaking. Beautiful sunsets. Enjoyed a crazy night of ping pong, playing cards and online Jackbox games. Plenty of space and loved the large kitchen and bathroom for every bedroom. None of us wanted to leave."

living room, there is TV with netflix/ prime streaming.

"Great place to stay while in the area. Thank you!"

"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."

AED 1,870 total

includes taxes & fees

5 Mar - 6 Mar

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Other property types in Charlotte Hall

"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."