Search Holiday Rentals in Southern Maryland

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Top Holiday Rentals in Southern Maryland

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, 108 reviews
"What a nice spot to unplug and relax! Waterfront property in a super quiet neighborhood. Hosts live next door; friendly and helpful, excellent communication. House was spotless, bed and furniture was comfortable, kitchen was all set up, spacious bathroom. There is a great screened porch that we spent most of our time on. Lots of wildlife to watch. Dog friendly with a big lot to enjoy. They have a nice grill and a fire pit. We also enjoyed a great dinner at Captain Billy's Crab House. Will be...
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
3.0 star property
10.0 out of 10, Exceptional, 1 review
"Suite was clean. Quiet you could not hear neighbors."
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
Wyndham at National Harbor - 2 Bedroom Deluxe
4.0 star property
9.4 out of 10, Exceptional, 6 reviews
"The room we stayed in was, without a doubt, beautiful. It was clean, spacious, and the amenities were many. However, until check-in we were completely unaware of the fact that we would be forced to attend a sales pitch for ownership at the resort. I would never have booked this listing had I known that.it was a very unfortunate discovery upon arrival, and a huge inconvenience during our family vacation."
Wyndham at National Harbor - 2 Bedroom Deluxe
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Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, 49 reviews
"Beautiful little house right on the beach of the Chesapeake. Loved it. Everything was great and we will definitely be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
Piney Point, private , Beach Front Cottage
10.0 out of 10, Exceptional, 76 reviews
"We are so grateful to have had some time in this wonderful home. It was amazing to have the water at our back door. Every member of the family loved our stay here. Thank you so much!"
Piney Point, private , Beach Front Cottage
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, 25 reviews
"I chose to stay at this property for the duration of my wedding weekend. It was really great to be able to spend that extra time with family all together! Getting ready at the house, rather than a hotel was also really nice because we had much more room to space out. The make up artist and hair stylist also complimented the ample natural light and space to work. The pool and hot tub were beautiful! The only downside was a lack of curtains in the master bedroom. The sunrise is beautiful but...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, 4 reviews
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Waterfront Relaxing Getaway
10.0 out of 10, Exceptional, 11 reviews
"I was looking for a nice, quiet, and relaxing, vacation. This property did not disappoint. The house was comfortable, cozy, well stocked, and so clean. The view is incredible. Just sitting outside watching the river was so "Zen". I had one of the most restful vacations ever. I was there for a little over two weeks and I would have stayed longer if I could have, Kim, the host, was very friendly and helpful. I look forward to staying at this beautiful property again."
The price is €402
per night
26 Jun - 27 Jun
Waterfront Relaxing Getaway
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, 102 reviews
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, 35 reviews
"Great place for a short moms getaway. Walking distances to many things. Heard live music from the porch. House is spacious and extremely clean"
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, 8 reviews
"we really, really like the retro look and really enjoyed the space. It was quiet and we were able to relax."
The price is €276
per night
25 Jun - 26 Jun
Soul Oasis - home on the Chesapeake Bay
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, 40 reviews
"Property and home were in excellent condition. Home made us feel welcome and secure. Host provides extras that make your stay convenient. Close to the restaurants and ice cream shop that serves Hershey ice cream. Love the people and neighborhood."
The Blue Crab Beach House - Free beach passes
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, 31 reviews
"Had an amazing time staying here. Place was just as beautiful as the pictures. Enjoyed time on the beaches and in the town. House was very relaxing and quiet making for an amazing stay."
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Dee's Lounge, Your Relaxation Oasis
9.8 out of 10, Exceptional, 7 reviews
"This home was beautiful and very accommodating for my guest and I. It was nice, cozy and clean and I didn’t need anything because she had it there. I will definitely book this again when I’m in the area. Thank you for your hospitality."
The price is €510
per night
24 Jun - 25 Jun
Dee's Lounge, Your Relaxation Oasis
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, 172 reviews
"Groomsmen stayed here for wedding. Great experience in a beautiful location. Swimming and kayaking right out the back door. Owners were very kind and helpful. Definitely recommend this beautiful spot."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Private Waterview Estate with 4 bedroom Suites & Hot Tub
9.8 out of 10, Exceptional, 18 reviews
"Great location and house! We all had a great time!"
Private Waterview Estate with 4 bedroom Suites & Hot Tub
Chesapeake Bay Vacation Rental w/ Boat Dock!
8.8 out of 10, Excellent, 5 reviews
"It was not as clean as it should have been. When i pay to stay somewhere, i expect clean."
Chesapeake Bay Vacation Rental w/ Boat Dock!
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
10.0 out of 10, Exceptional, 53 reviews
"We enjoyed this vacation home. It offer a wonderful location and lots of quality family time."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, 5 reviews
"We were in town for a friends wedding. This was the perfect location as it was right in between the Catholic Church for the nuptial mass and the reception site. This place certainly did not disappoint. There was plenty of space for our large family, the home was well equipped and stocked with the necessary items. It was a relatively short stay, but I wish we had a bit more time and better weather to enjoy the use of kayaks - our one free morning was a bit chilly for us Florida folks, and we had...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
2.0 star property
10.0 out of 10, Exceptional, 2 reviews
"Inside: We had a two-room setup (king bed and adjoining bathroom that had a stall and tub; then two queen beds and bath off the dining room). The room was very comfortable and spacious. The kitchen was great. We were given great starter amenities; The only issue we had was that we were unclear on whether we could ask for more or the cleaning staff to come in. The vibe seemed weird around Vrbo customers; it was not worth it to us to kick up dust. Additionally, the second floor community amenities...
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
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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.

Other types of properties in Southern Maryland you may be interested in

Gaylord National Resort & Convention Center
4.0 star property
8.4 out of 10, Very good, 1,008 reviews
"Great conference venue."
The price is €271
per night
21 Jul - 22 Jul
Gaylord National Resort & Convention Center
Holiday Inn Express Washington DC East - Andrews AFB, an IHG Hotel
2.5 star property
8.0 out of 10, Very good, 1,003 reviews
"Nice hotel close to metro station. Made traveling into DC very easy. Room was in good condition. Only inconvenience was back parking lot keycard to open the door was broken. If I return to DC again and choose to stay somewhere outside downtown area. I would definitely consider this hotel again."
The price is €104
per night
5 Jul - 6 Jul
Holiday Inn Express Washington DC East - Andrews AFB, an IHG Hotel
Hampton Inn & Suites National Harbor - Alexandria Area
2.5 star property
8.8 out of 10, Excellent, 1,001 reviews
"Denali was very friendly and accomodating. Room was really nice and clean. "
The price is €158
per night
2 Jul - 3 Jul
Hampton Inn & Suites National Harbor - Alexandria Area
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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