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Compare 120 Vacation Homes in Charlotte Hall with updated reviews, rates, and availability.

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
The driveway allows for plenty of parking for guests!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.6 out of 10, Exceptional, (29)
"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 RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Charming 3-bedroom retreat in White Plains
Private kitchen

Charming 3-bedroom retreat in White Plains

The price is AED 400
AED 561 total
includes taxes & fees
18 Jan - 19 Jan
Charming 3-bedroom retreat in White Plains
Waterfront Relaxing Getaway
Property grounds

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (19)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Sunroom off the kitchen and living room with a magnificent view of the Chesapeake Bay

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (112)
"Very nice place we found, great views, very clean, quiet, great place to relax for the weekend. everything went well and we would highly recommend anyone for a stay here. we will be back next year"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
The Lyellton House: Waterview Home within walking distance to many amenities
Evening at the Lyellton House

The Lyellton House: Waterview Home within walking distance to many amenities

9.8 out of 10, Exceptional, (8)
"From beginning to end - absolutely perfect! Property owner was the best! Extremely helpful & organized! The property was amazing and worked just great for our Family - Adults and children. The home was beautiful, clean and had everything you could think of and would need for an excellent getaway!! Thank you!"
The price is AED 1,080
AED 2,597 total
includes taxes & fees
5 Jan - 6 Jan
The Lyellton House: Waterview Home within walking distance to many amenities
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
Sit on the patio and enjoy your coffee in the morning.

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

9.8 out of 10, Exceptional, (19)
"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
living room, there is TV with netflix/ prime streaming.

Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

10.0 out of 10, Exceptional, (10)
"Great place to stay while in the area. Thank you!"
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
Waterfront home on Monroe Bay in the heart of Colonial Beach.

Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area

10.0 out of 10, Exceptional, (25)
"We had a great time. House was very roomy, and the views were lovely. Would love to visit again."
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
Spectacular Waterfront Retreat with Pier

Spectacular Waterfront Retreat with Pier

10.0 out of 10, Exceptional, (7)
"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!"
Spectacular Waterfront Retreat with Pier
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown
Open concept living room and kitchen allows family and friends to stay together to socialize and reconnect.

Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

10.0 out of 10, Exceptional, (12)
"Myself, my partner, my 7 family members and our 2 pups stayed here for our annual vacation to Colonial Beach & our experience was nothing short of spectacular. The host is super fast at replying, made our check in process easy, and was super hospitable. They even accommodated our last minute wish to check in early! The ONLY thing I can think of that can be improved is the level of cleanliness. Everything was beautiful and clean except for areas underneath the rugs, which were covered with sand...
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown
Waterfront Lusby Escape w/ Fire Pit & Kayaks!
Lusby Vacation Rental | 4BR | 3BA | 3,720 Sq Ft | Stairs Required

Waterfront Lusby Escape w/ Fire Pit & Kayaks!

10.0 out of 10, Exceptional, (6)
"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."
Waterfront Lusby Escape w/ Fire Pit & Kayaks!
Tranquil Private Getaway Minutes to Patuxent River
Living area

Tranquil Private Getaway Minutes to Patuxent River

10.0 out of 10, Exceptional, (1)
Tranquil Private Getaway Minutes to Patuxent River
Hawthorn House Remodeled 3BR Walk to Town!
Welcome to Hawthorn House, centrally located and just 1 block from main street!

Hawthorn House Remodeled 3BR Walk to Town!

10.0 out of 10, Exceptional, (3)
"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...
Hawthorn House Remodeled 3BR Walk to Town!
Waterfront Leonardtown Retreat w/ Dock Access!
Leonardtown Vacation Rental | 4BR | 4BA | 6,500 Sq Ft | Steps Required

Waterfront Leonardtown Retreat w/ Dock Access!

10.0 out of 10, Exceptional, (1)
"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."
Waterfront Leonardtown Retreat w/ Dock Access!
3 Bedrooms Relaxing Rustic House on Saint Thomas CreeK
Property grounds

3 Bedrooms Relaxing Rustic House on Saint Thomas CreeK

3 Bedrooms Relaxing Rustic House on Saint Thomas CreeK
Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly
Exterior

Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly

10.0 out of 10, Exceptional, (5)
"This property is outstanding! Absolutely spotless and host super to work with. Great neighborhood, easy walking and our dogs loved it too!"
Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
Living area

2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!

10.0 out of 10, Exceptional, (2)
"Quite and friendly neighbors "
The price is AED 771
AED 1,448 total
includes taxes & fees
6 Jan - 7 Jan
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
Unplug and unwind at your Leonardtown waterfront vacation home!
Miscellaneous

Unplug and unwind at your Leonardtown waterfront vacation home!

8.8 out of 10, Excellent, (5)
"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."
Unplug and unwind at your Leonardtown waterfront vacation home!
Waterfront home, dock, pool, pickleball, dog-friendly, fireplaces, a/c, jacuzzi

Waterfront home, dock, pool, pickleball, dog-friendly, fireplaces, a/c, jacuzzi

2.0 star property
10.0 out of 10, Exceptional, (2)
Waterfront home, dock, pool, pickleball, dog-friendly, fireplaces, a/c, jacuzzi
4BDRM River front house with Private Beach in Hollywood
Property grounds

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.6 out of 10, Exceptional, (5)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Charlotte Hall

Cozy Cottage with access to and partially obstructed views of the bay.
Exterior

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (16)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Outdoor dining

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

10.0 out of 10, Exceptional, (38)
"Heather and Ed are superb hosts. The home was very clean, well stocked and in the perfect location! "
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (124)
"We chose to celebrate our 10th wedding anniversary here for a quiet weekend away with our dog. The house provided everything we needed and the owners were great to deal with. Highly recommend!! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.