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Southern Maryland Vacation Rentals

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Our top choices for Southern Maryland vacation rentals

1. 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 CA $182
CA $435 total
includes taxes & fees
Oct 25 - Oct 26
The Cozy Crab- Your Charming Haven in Lovely North Beach!

2. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is CA $238
CA $406 total
includes taxes & fees
Nov 2 - Nov 3
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

3. 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 CA $148
CA $489 total
includes taxes & fees
Nov 2 - Nov 3
Beachside Oasis with Beach Passes & King Suite by A Haven Away

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 CA $136
CA $559 total
includes taxes & fees
Oct 25 - Oct 26
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

5. Just a getaway piece of property

Just a getaway piece of property
Mechanicsville
10.0 out of 10, Exceptional, (1 review)
"Perfect place. Just what i was looking. Definitely recommend to anyone looking to stay close to the MIR track for any event"
United States
David L.
The price is CA $221
CA $319 total
includes taxes & fees
Oct 28 - Oct 29
Just a getaway piece of property

6. 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 CA $322
CA $536 total
includes taxes & fees
Nov 2 - Nov 3
Bright and airy waterfront getaway

7. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is CA $223
CA $512 total
includes taxes & fees
Nov 15 - Nov 16
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

8. 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 CA $193
CA $396 total
includes taxes & fees
Oct 27 - Oct 28
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

9. 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 CA $221
CA $399 total
includes taxes & fees
Nov 1 - Nov 2
MOUNT VERNON RETREAT 🌸

10. 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 CA $347
CA $709 total
includes taxes & fees
Nov 10 - Nov 11
Sunset Cottage - West River Access and Views!

11. 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)
"A great place to crash and explore the area."
United States
Sean B.
The price is CA $217
CA $518 total
includes taxes & fees
Nov 2 - Nov 3
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

12. Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is CA $335
CA $825 total
includes taxes & fees
Oct 25 - Oct 26
Anne & Fred`s Leonardtown Home W/ Arcade room!

13. 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 CA $239
CA $528 total
includes taxes & fees
Nov 18 - Nov 19
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

14. 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 CA $252
CA $611 total
includes taxes & fees
Oct 27 - Oct 28
3-bedroom house in Deale located on Bay many amenities and great views

15. 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 CA $280
CA $581 total
includes taxes & fees
Oct 27 - Oct 28
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

16. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.0 out of 10, Wonderful, (22 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is CA $314
CA $617 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

17. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is CA $479
CA $793 total
includes taxes & fees
Oct 25 - Oct 26
Plum Point Cottage #14

18. 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 CA $420
CA $1,042 total
includes taxes & fees
Oct 25 - Oct 26
4-BR Waterfront Turret Home

19. 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 CA $493
CA $1,373 total
includes taxes & fees
Oct 27 - Oct 28
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

20. SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden

SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden
Fort Washington
9.6 out of 10, Exceptional, (19 reviews)
"The property was very spacious and clean. Nice neighborhood."
United States
tracey
The price is CA $478
CA $1,068 total
includes taxes & fees
Nov 2 - Nov 3
SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden
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

Find out more about Southern Maryland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Southern Maryland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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