Southern Maryland Holiday Rentals

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Check prices for these dates

Tonight
2 Feb - 3 Feb
Tomorrow
3 Feb - 4 Feb
Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 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.

9.6 out of 10, Exceptional, (17)
"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, (18)
"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 AU$469
includes taxes & fees
3 Feb - 4 Feb
Soul Oasis - home on the Chesapeake Bay
Screened Patio, Deck & Grill: Saint Inigoes Home!
Outdoor dining

Screened Patio, Deck & Grill: Saint Inigoes Home!

Screened Patio, Deck & Grill: Saint Inigoes Home!
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, (126)
"Great location by the water and far enough from the hustle and bustle. Perfect size cottage for us for a relaxing new year’s celebration. "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
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!

9.6 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!
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
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
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
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
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 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 AU$699
includes taxes & fees
3 Feb - 4 Feb
The Cottage
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
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)
"The cabin was great, very cozy and clean. Host was very communicative and helpful. Overall an excellent stay!"
El Camino
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
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 AU$833
includes taxes & fees
3 Feb - 4 Feb
4-BR Unique Waterfront House - Your Perfect Escape
Hays Beach House - Hot Tub - Private Beach
Smart TV, fireplace, books

Hays Beach House - Hot Tub - Private Beach

10.0 out of 10, Exceptional, (4)
"We booked this bayside property for a short family vacation and the house and amenities were exactly what we needed during our time at Hays Beach. There were ample bedrooms and spaces for all of us to relax, the kitchen was well appointed. The beach in front of the house was perfect for our grandson to play in a small pool while the others lounged in chairs or were in the water directly in front of the house. The public beach was a short walk away and we enjoyed seeing all the wildlife on the...
Hays Beach House - Hot Tub - Private Beach
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.
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, (1010)
"Nice"
The price is AU$412
includes taxes & fees
17 Feb - 18 Feb
Gaylord National Resort & Convention Center
Holiday Inn Express Waldorf, an IHG Hotel
Exterior

Holiday Inn Express Waldorf, an IHG Hotel

2.5 star property
8.2 out of 10, Very good, (865)
"Parking lot fill of ice and snow, made it hard to park & hard to get in & out of vehicle without stepping on ice, sleet & snow."
The price is AU$183
includes taxes & fees
4 Feb - 5 Feb
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Econo Lodge Andrews Air Force Base
Desk, laptop workspace, blackout curtains, iron/ironing board

Econo Lodge Andrews Air Force Base

2.0 star property
6.4 out of 10, (1002)
"For the price and what's around it, its worth it."
The price is AU$116
includes taxes & fees
10 Feb - 11 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.