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Compare 115 Vacation Homes in Charlotte Hall with updated reviews, rates, and availability.

Discover the charm of Colonial Beach
Discover the charm of Colonial Beach
10.0 out of 10, Exceptional, (3)
"I was in the area for one night for business and had my young granddaughter with me. The room was very comfortable and well furnished. Lots of apps available on the TV. Location is close to plenty of restaurants and the beach. The continental breakfast was very nicely set and had lots of variety. I plan on coming back NOT for business just so I can enjoy another stay. Highly recommend."
The price is SAR 533
SAR 657 total
includes taxes & fees
14 Nov - 15 Nov
Discover the charm of Colonial Beach
Historic charm with modern amenities
Historic charm with modern amenities
2.0 star property
10.0 out of 10, Exceptional, (1)
"The room we stayed in had a separate bedroom, living room and bathroom. Oversized refrigerator was handy. Will definitely stay here again."
The price is SAR 616
SAR 702 total
includes taxes & fees
14 Nov - 15 Nov
Historic charm with modern amenities
Inviting and Serene Home on Monroe Bay Creek
View from back deck looking onto the private dock and creek
Inviting and Serene Home on Monroe Bay Creek
10.0 out of 10, Exceptional, (62)
"Absolutely lovely property. Everything is modern and clean. Beautiful nautical decor. On the water with lots of room and space. We loved it so much, we plan to use it again!!!"
Inviting and Serene Home on Monroe Bay Creek
Waterfront with spectacular view, close to restaurants and bars
Exterior
Waterfront with spectacular view, close to restaurants and bars
10.0 out of 10, Exceptional, (29)
"Would definitely stay again"
Waterfront with spectacular view, close to restaurants and bars
WATERFRONT!!! The River's Roost on The Patuxent River
Property grounds
WATERFRONT!!! The River's Roost on The Patuxent River
10.0 out of 10, Exceptional, (18)
"This house is absolutely fabulous! Very spacious, stocked with necessary supplies and many amenities. Beautiful property and views of the water, sunrises and sunsets. We especially liked all the wonderful decks, kitchen on the bottom level, many bathrooms, and comfortable furnishings. John and Christina were excellent host. They responded immediately to any concerns or questions. They were easy to communicate with during the check-in and check-out process. I would definitely love to...
WATERFRONT!!! The River's Roost on The Patuxent River
Colonial Beach Cottage, 7 minutes walk to beach!
Large front deck with lights and private fenced yard
Colonial Beach Cottage, 7 minutes walk to beach!
9.8 out of 10, Exceptional, (21)
"Very clean and comfortable. Fenced in lot was great for letting our dog walk around off leash. Off street parking was a plus. Don't miss breakfast at Lenny's a short walk away or the model train store next door."
Colonial Beach Cottage, 7 minutes walk to beach!
Secluded waterfront house to relax or enjoy water activities from private pier
backyard and pier
Secluded waterfront house to relax or enjoy water activities from private pier
9.8 out of 10, Exceptional, (25)
"Overall very pleased. Seemed like a lot of money for the property but I guess that’s what waterfront cost. House was very clean and well equipped. Loved the mini-splits in each room. The only reason I gave “cleanliness” four stars is because the outside trash can had a bunch of trash the smelled horrible and the recycling container also had trash in it. Michelle was great and very responsive. There’s a great market on the island but very few dining options and no fine dining. Very cozy...
Secluded waterfront house to relax or enjoy water activities from private pier
Riverside House w/ Kayaks, Piano & Fireplace
California Vacation Rental | 5BR | 2.5BA | 2,300 Sq Ft | Stairs Required
Riverside House w/ Kayaks, Piano & Fireplace
8.8 out of 10, Excellent, (10)
"Clean property and just what we needed to gather with family nearby"
Riverside House w/ Kayaks, Piano & Fireplace
Blue Heron Retreat on the Water
Private dock for kayaking , swimming , boating , fishing, and even crabbing
Blue Heron Retreat on the Water
10.0 out of 10, Exceptional, (10)
"The place was as described. Great communication and check in. All professional."
Blue Heron Retreat on the Water
Waterfront Relaxing Getaway
Property grounds
Waterfront Relaxing Getaway
9.8 out of 10, Exceptional, (18)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway
Mid-Century Modern and Marvelous on the Bay
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (69)
"Hands down our favorite place to stay! Would love to keep in a secret, but need to sing its praises. Nick is awesome and answers any questions you may have. The house is well appointed, lovely neighborhood and location is perfect to rest and relax. "
Mid-Century Modern and Marvelous on the Bay
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, (18)
"The property is perfect for family gatherings "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
"High Tide Tranquility"- Beach w/ BBQ
Private Community Beach
"High Tide Tranquility"- Beach w/ BBQ
10.0 out of 10, Exceptional, (5)
"Thank you Dawn!! She helped out after a double booking for another property. She was super accommodating to a last minute booking! The house is fantastic, it couldn’t have been more perfect for my husband and I, and a friend. It was located close to both Prince Frederick and Solomon’s Island. The beach access was great! We found a few teeth. Thank you for such a nice stay!! "
"High Tide Tranquility"- Beach w/ BBQ
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
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
Spacious comfy Home in White Plains / Waldorf close to DC and National harbor
Master bedroom California king bed
Spacious comfy Home in White Plains / Waldorf close to DC and National harbor
8.0 out of 10, Very Good, (1)
The price is SAR 1,003
SAR 2,063 total
includes taxes & fees
19 Nov - 20 Nov
Spacious comfy Home in White Plains / Waldorf close to DC and National harbor
Bright and airy waterfront getaway
Our 400 foot pier, great for fishing crabbing watching Osprey's or hanging out
Bright and airy waterfront getaway
9.6 out of 10, Exceptional, (10)
"This property was everything we wanted. We hope to return next year."
Bright and airy waterfront getaway
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
Unplug and unwind at your Leonardtown waterfront vacation home!
Miscellaneous
Unplug and unwind at your Leonardtown waterfront vacation home!
8.6 out of 10, Excellent, (4)
"We had a wonderful time staying at the property. The accommodations exceeded our expectations! The house was immaculately clean and comfortable. The location was perfect! Close to Leonardtown and beaches. Our hosts went above and beyond to make sure we had everything we needed and their communication made the entire experience seamless. Highly recommend this property. We are excited to return! "
Unplug and unwind at your Leonardtown waterfront vacation home!
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

Mid-Century Modern and Marvelous on the Bay
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (69)
"Hands down our favorite place to stay! Would love to keep in a secret, but need to sing its praises. Nick is awesome and answers any questions you may have. The house is well appointed, lovely neighborhood and location is perfect to rest and relax. "
Mid-Century Modern and Marvelous on 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, (36)
"Perfect size house. Clean/Comfortable Use of golf cart to get around was awesome. I’m already looking at my calendar for 2025 to come back. "
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, (123)
"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.