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Compare 153 Vacation Homes in Charlotte Hall with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (113)
"This place was a wonderful spot for our family to have a long weekend getaway. It's on a bluff right next to the ocean with a glorious view and a stairway access to the beach. The beds are comfortable, the house has lots of great spaces to relax or play games, and the beach is a wonderful space to explore, find seashells and possibly a fossil sharks tooth (we had no luck there, but we did find a whale vertebrae, so that's something!). But in any event, we highly recommend! "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area

10.0 out of 10, Exceptional, (30)
"My husband and i live up the road but we rented this house for his parents, for the weekend. The location is absolutely fantastic and the house is gorgeous. I could have sat on the back deck for hours. Dan was very responsive to all of my questions. I wouldn't hesitate to rent from him, again. "
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area

1 Mi to Colonial Beach Boardwalk: Home w/ Fire Pit

10.0 out of 10, Exceptional, (1)
1 Mi to Colonial Beach Boardwalk: Home w/ Fire Pit

Waterfront with spectacular view, close to restaurants and bars

10.0 out of 10, Exceptional, (31)
"Everything was great. "
Waterfront with spectacular view, close to restaurants and bars

Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub

Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub

Inviting and Serene Home on Monroe Bay Creek

10.0 out of 10, Exceptional, (64)
"This is such a perfect home and property on the river with many fun things to do. And an amazing host to go along with it, who provided many small details and touches that we didn’t expect, but truly enhanced the visit. Thanks!"
Inviting and Serene Home on Monroe Bay Creek

Perfect Pointe, Cobb Island, Maryland

10.0 out of 10, Exceptional, (52)
"Family adventure with our two adult children and their families. Perfect Pointe met all our needs and more. The house had plenty of space and comfort throughout. Outdoors provided numerous opportunities for any number of interests. Definitely plan a return! The Kling Family."
Perfect Pointe, Cobb Island, Maryland

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"We stayed for a motorcross race (son was racing). We didnt do much at the house. Its nestled back in a quiet point on the water. Easy commute to and from to the grocery/simple shopping stores. Starbucks right down the street for you coffee lovers. The interior decor is simple and antique."
Waterfront House with Dock, Kayaks, & Sailboat!

5 bedroom, 8 bed, 3 story house a block from beach

9.6 out of 10, Exceptional, (13)
"Everything went extremely smooth. Check in was easy. House was nice and clean. Had a lot of fun with the gaming stuff they had set up! The house had everything you could imagine and more! Owners were extremely nice and informative. Recommended good places to go and eat. Overall great experience and would definitely go again."
5 bedroom, 8 bed, 3 story house a block from beach

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

10.0 out of 10, Exceptional, (77)
"An absolutely beautiful, architecturally fascinating, spotlessly clean, well stocked home with views that go on for literally miles. We spent a late winter weekend there with a fire roaring in the fireplace and mussels on the stove. Hosts were exceptionally responsive and very attentive. Highly recommended. One of the best experiences we've ever had in home rentals! "
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay

10.0 out of 10, Exceptional, (43)
"Great time! First time in Colonial Beach. Low key family time. House was perfect location for us. Very enjoyable!"
Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay

4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick

4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick

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

Family Beach House: Spacious Deck, Grill & Views

9.6 out of 10, Exceptional, (4)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is AED 878
AED 1,911 total
includes taxes & fees
12 May - 13 May
Family Beach House: Spacious Deck, Grill & Views

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

10.0 out of 10, Exceptional, (13)
"Very clean, great location, and comfortable beds, we had a great time. Walking distance to bars, restaurants, and coffee shops. Very convenient, and the owner was easy to work with. "
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

New! Cozy River Cottage with great views of the water!

9.6 out of 10, Exceptional, (5)
"A very nice house with an amazing view 10/10 recommend"
New! Cozy River Cottage with great views of the water!

Colonial Beach Cottage, 7 minutes walk to beach!

9.6 out of 10, Exceptional, (26)
"We had a wonderful time at your cottage. It was in a great location with easy access to walk to the water and restaurants. Our dog loved the fenced in yard too! We would definitely recommend this place to others. Thank you for sharing your cottage."
Colonial Beach Cottage, 7 minutes walk to beach!

Cottage on The Point! Bring your bikes & golf cart, and your pets!

10.0 out of 10, Exceptional, (25)
"The cottage was very clean and had everything we needed. Lots of nice details and our two fur babies loved the big backyard. Thank you for a relaxing week! We will definitely be back."
Cottage on The Point! Bring your bikes & golf cart, and your pets!

Riverside House w/ Kayaks, Piano & Fireplace

9.0 out of 10, Wonderful, (13)
"This house is well-maintained and my business associates enjoy staying here. We will book this house every time it comes available."
Riverside House w/ Kayaks, Piano & Fireplace

Crab Shack in Town-Walk to beach and restaurants-Sleeps 6

10.0 out of 10, Exceptional, (5)
"This property was great! My family was very happy with the location in relation to the beach, gym, and a basketball court. They are already talking about coming back to this property."
Crab Shack in Town-Walk to beach and restaurants-Sleeps 6
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

Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area

10.0 out of 10, Exceptional, (30)
"My husband and i live up the road but we rented this house for his parents, for the weekend. The location is absolutely fantastic and the house is gorgeous. I could have sat on the back deck for hours. Dan was very responsive to all of my questions. I wouldn't hesitate to rent from him, again. "
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area

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

9.8 out of 10, Exceptional, (128)
"Great little weekend getaway very quiet and enjoyed the relaxation . Very cute and clean cottage on the water "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"We stayed for a motorcross race (son was racing). We didnt do much at the house. Its nestled back in a quiet point on the water. Easy commute to and from to the grocery/simple shopping stores. Starbucks right down the street for you coffee lovers. The interior decor is simple and antique."
Waterfront House with Dock, Kayaks, & Sailboat!
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.