Southern Maryland Holiday Rentals

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Check prices for these dates

Tonight
13 Feb - 14 Feb
Tomorrow
14 Feb - 15 Feb
This weekend
14 Feb - 16 Feb
Next weekend
21 Feb - 23 Feb

Holiday Rentals in Southern Maryland

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Cozy Cottage with access to and partially obstructed views of the bay.
Miscellaneous

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

9.4 out of 10, Exceptional, (18)
"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."
Cozy Cottage with access to and partially obstructed views of the bay.
Soul Oasis - home on the Chesapeake Bay
Sun-loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (19)
"Beautiful place, very clean and nicely decorated. The only thing I wish was better was to have a bathroom upstairs and the stairs to be a bit easier to access, they are a bit tricky for those over 50:) nice view too!"
The price is NZ$502
includes taxes & fees
18 Feb - 19 Feb
Soul Oasis - home on the Chesapeake Bay
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, (127)
"This was our mid-Winter get away from the city. The home is cute, quiet, and well appointed. The host is welcoming and responsive. We had a lovely, restful stay. "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Screened Patio, Deck & Grill: Saint Inigoes Home!
Outdoor dining

Screened Patio, Deck & Grill: Saint Inigoes Home!

Screened Patio, Deck & Grill: Saint Inigoes Home!
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (30)
"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!
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (49)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
On the beach

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
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
MD/VA/DC. Smallwood State Park
Exterior

MD/VA/DC. Smallwood State Park

9.6 out of 10, Exceptional, (18)
"I had a research project with a large number of students. The location was excellent for this purpose. The hosts were very receptive to requests. The location is highly recommended!"
MD/VA/DC. Smallwood State Park
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
Living area

Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

10.0 out of 10, Exceptional, (5)
"Nice location. The house had everything we needed for our stay. The host was available by phone for any questions we had. I would stay again the next time I visit North Beach"
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
The Lazy Crab Beach House - Free beach passes
Property grounds

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (43)
"Would stay again."
The Lazy Crab Beach House - Free beach passes
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (2)
"Couldn’t have asked for better- I appreciate the communication and willingness to work with us on a quick turn around trip. Clean. Easy to get to. Accurate description. Quiet neighborhood. 10/10 would stay again. "
The price is NZ$754
includes taxes & fees
16 Feb - 17 Feb
The Cottage
Belle of the Chesapeake Bay
Beach

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (12)
"Our granddaughters live in the neighborhood and our youngest was having her first birthday! It was just my husband and myself, way more house than we needed but tons more comfortable than a hotel. The winter views of the Bay from the living room were awesome. I highly recommend you make a cup of coffee and watch the sunrise. A few surprises with the house itself, the most egregious for me was the fireplace pictured is not functional. The hosts have done a nice job with this house and are still...
Belle of the Chesapeake Bay
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Beach

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

9.8 out of 10, Exceptional, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
El Camino
Terrace/patio

El Camino

10.0 out of 10, Exceptional, (33)
"Very cute cabin. We enjoyed the peace and quiet. Ver close to our destin.ation, Point lookout."
El Camino
Guest quarters at the inn - 205
TV

Guest quarters at the inn - 205

9.4 out of 10, Exceptional, (12)
"The property was not only as described, but better than described, honestly words don’t do it justice. It was exactly what my best friend and I needed to get ready for a friends wedding, and have a comfortable place to stay for the weekend. We loved the classy decor, full length, mirror, soaking tub, and the big thank you for the welcome tray of snacks! The location is perfect, a block from the water, close to bars and restaurants, while being in a quiet neighborhood, and it’s proximity to...
Guest quarters at the inn - 205
4-bedroom house in awesome Temple Hills with AC, WiFi. Enjoy your stay
Private kitchen

4-bedroom house in awesome Temple Hills with AC, WiFi. Enjoy your stay

2.0 star property
2.0 out of 10, (1)
"The house was being used by someone else at the time of my reservation. I never got the code to the house but i was charged the money. And i never got an answer from the property manager. If you are looking to rent this property save your money because i was scammed."
4-bedroom house in awesome Temple Hills with AC, WiFi. Enjoy your stay
Private Beach Front Getaway at The Sunshine Beach Cottage.
On the beach, sun-loungers, beach towels

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (63)
"Beautifully appointed cottage. Literally right on the water. Quiet, serene and relaxing. Loved it and will be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
4-BR Unique Waterfront House - Your Perfect Escape
Interior

4-BR Unique Waterfront House - Your Perfect Escape

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
The price is NZ$894
includes taxes & fees
20 Feb - 21 Feb
4-BR Unique Waterfront House - Your Perfect Escape
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 types of properties in Southern Maryland you may be interested in

Gaylord National Resort & Convention Center
Exterior

Gaylord National Resort & Convention Center

4.0 star property
8.6 out of 10, Excellent, (1007)
"I've stayed at the Gaylord a number of times over the last 10 years. Service has always been excellent, staff always ready to help. This time around I needed room service more than ever, it was super fast and the staff was very patient with repeat calls. If I had to advise anyone anything, if you have sensitive breathing issues: Bring a humidifier. Particularly, if you intend on staying for more than a couple days. Maybe its because I've gotten older, but the rooms are very very dry. *This may...
The price is NZ$544
includes taxes & fees
14 Mar - 15 Mar
Gaylord National Resort & Convention Center
Holiday Inn Express Waldorf by IHG
Exterior

Holiday Inn Express Waldorf by IHG

2.5 star property
8.2 out of 10, Very good, (871)
"Friendly staff...nice breakfast and very clean."
The price is NZ$192
includes taxes & fees
2 Mar - 3 Mar
Holiday Inn Express Waldorf by IHG
Econo Lodge Andrews Air Force Base
Desk, laptop workspace, blackout curtains, iron/ironing board

Econo Lodge Andrews Air Force Base

2.0 star property
6.2 out of 10, (999)
"Overall it was suitable and good."
The price is NZ$127
includes taxes & fees
19 Feb - 20 Feb
Econo Lodge Andrews Air Force Base
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.