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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Southern Maryland vacation homes

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

1. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is ￥16,526
￥52,568 total
includes taxes & fees
Nov 9 - Nov 10
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

2. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is ￥20,375
￥48,013 total
includes taxes & fees
Oct 25 - Oct 26
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A lakeside view with chairs and a table, a rainbow, and trees.

3. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is ￥36,048
￥59,974 total
includes taxes & fees
Nov 2 - Nov 3
Bright and airy waterfront getaway
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

4. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is ￥13,863
￥60,078 total
includes taxes & fees
Oct 25 - Oct 26
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

5. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is ￥21,300
￥43,344 total
includes taxes & fees
Nov 2 - Nov 3
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

6. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"The house was cute and walkable to the bay. The bedrooms are large and there is plenty of space."
United States
Amy S.
The price is ￥24,293
￥57,150 total
includes taxes & fees
Nov 2 - Nov 3
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
A two-story house with a deck and a staircase leading to the upper floor.

7. MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
9.8 out of 10, Exceptional, (150 reviews)
"What a beautiful and quaint little place to stay! So peaceful and the hosts were absolutely delightful! We will definitely be back!"
United States
Tiffany Z.
The price is ￥24,685
￥44,612 total
includes taxes & fees
Nov 1 - Nov 2
MOUNT VERNON RETREAT 🌸
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

8. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is ￥38,869
￥79,189 total
includes taxes & fees
Nov 10 - Nov 11
Sunset Cottage - West River Access and Views!
A deck with outdoor furniture, a red door, and a house with windows.

9. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is ￥26,801
￥59,498 total
includes taxes & fees
Nov 18 - Nov 19
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

10. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is ￥28,211
￥68,431 total
includes taxes & fees
Oct 27 - Oct 28
3-bedroom house in Deale located on Bay many amenities and great views
A spacious living room with a large sofa, a television, and a view of the ocean.

11. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is ￥47,019
￥109,786 total
includes taxes & fees
Oct 25 - Oct 26
4-BR Waterfront Turret Home
A residential property with a staircase leading to a front door, surrounded by a well-maintained lawn and a variety of plants.

12. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (4 reviews)
"Warm and cozy- amazing home, beautiful area"
United States
Sodbileg
Rose Haven Coastal Cottage
A covered patio with a view of a lake, furnished with chairs and a table.

13. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (18 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is ￥31,346
￥64,065 total
includes taxes & fees
Nov 9 - Nov 10
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

14. 2 Acre Oasis with Private Beach! Family and dog friendly!

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (67 reviews)
"Everything about this property is wonderful for our family! A dreamy relaxing vacation"
United States
Carol L.
The price is ￥62,065
￥132,683 total
includes taxes & fees
Oct 26 - Oct 27
2 Acre Oasis with Private Beach! Family and dog friendly!
A pathway lined with trees and lights leading to a wooden building with a visible window.

15. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (15 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveler
The price is ￥72,409
￥133,405 total
includes taxes & fees
Nov 8 - Nov 9
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A modern living room with a grey sofa, a dining table with chairs, and large windows with autumn foliage views.

16. Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"Overall I had a wonderful stay... however I wish it was booked for a summertime day... the brand new pool looked very appealing & I wish I couldve enjoyed using it. Will have to try & stay again during the summer for a nice pool day!"
United States
Jay W.
The price is ￥66,861
￥122,301 total
includes taxes & fees
Nov 2 - Nov 3
Tranquil Modern Farmhouse
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

17. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (4 reviews)
"Dude. This is what I always hope a rental property will be. Comfy beds, best stocked kitchen, working hot tub, beautiful waterfront area with kayaks and a dock. And our mini golden doodle could come too?! It was absolute perfection."
United States
Dani B.
The price is ￥55,169
￥151,476 total
includes taxes & fees
Oct 29 - Oct 30
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A bedroom with a bed, two bedside tables, a TV, and a window.

18. Modern 4BR Retreat • DC • MGM • National Harbor

Modern 4BR Retreat • DC • MGM • National Harbor
Fort Washington
The price is ￥31,346
￥54,581 total
includes taxes & fees
Nov 3 - Nov 4
Modern 4BR Retreat • DC • MGM • National Harbor
A two-story house with a balcony, surrounded by trees and a wooden fence.

19. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (7 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is ￥48,273
￥117,886 total
includes taxes & fees
Oct 30 - Oct 31
Charming Waterfront 3-bedroom house in Piney Point
A hallway with a wooden floor, a white wall, and a ceiling with a central light fixture. There is a door on the left and a mirror on the right.

20. Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room

Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room
La Plata
9.6 out of 10, Exceptional, (4 reviews)
"Cane for a weekend of Faith and Fun and this is exactly what we needed. Comfortably suited our 10 needs and so much more. Peaceful, serene, beautiful animals, game room, so much to say. Hostess with the mostest!!!! Charity is a gem! My church family will be back!!!!!"
United States
Wadiya D.
The price is ￥56,775
￥118,495 total
includes taxes & fees
Nov 9 - Nov 10
Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room
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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Top Southern Maryland Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"The Hotel was excellent. However, Expedia did not disclose that there was an additional charge for resort fee that was not included in the quoted price from Expedia. There was an additional $33.00 when I checked into the hotel. I could have gone with a different online reservation cheaper."
William 1-night trip
Posted 21 hours ago
Rod 'N' Reel Resort

Find out more about Southern Maryland

Southern Maryland Vacation Homes information

Number of reviews
290
Accommodation
298 Vacation Homes
Lowest Price
￥43,344
Highest Price
￥151,476

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