Southern Maryland Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in Southern Maryland

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (51)
"The Blue Crab Beach House was perfect for my wife and I and our dog. Very comfortable with a great backyard space for our dog. We loved the location - it’s just a short walk to restaurants and the bay. Very enjoyable stay and we hope to return."
The Blue Crab Beach House - Free beach passes

Club Wyndham National Harbor, Maryland, 1 Bedroom Deluxe Suite

Club Wyndham National Harbor, Maryland, 1 Bedroom Deluxe Suite

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!

Soul Oasis - home on the Chesapeake Bay

10.0 out of 10, Exceptional, (21)
"."
The price is NZ$442
includes taxes & fees
23 Apr - 24 Apr
Soul Oasis - home on the Chesapeake Bay

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (128)
"Great little weekend getaway very quiet and enjoyed the relaxation . Very cute and clean cottage on the water "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (160)
"The house was awesome, the view couldn’t have been better. Loved everything about it, quiet and peaceful and it is on a dead end short road with wildlife in the yard in the morning, deer, fox, blue heron, bald eagle, geese and ducks, just fabulous. Will definitely be going back soon I hope."
Waterfront Wildlife Retreat on the Patuxent River

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"We stayed for a motorcross race (son was racing). We didnt do much at the house. Its nestled back in a quiet point on the water. Easy commute to and from to the grocery/simple shopping stores. Starbucks right down the street for you coffee lovers. The interior decor is simple and antique."
Waterfront House with Dock, Kayaks, & Sailboat!

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is NZ$650
includes taxes & fees
18 Apr - 19 Apr
The Cottage

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (59)
"Property was exactly as advertised. Charming Farmhouse with plenty of space situated on a large property with a private beach. We even enjoyed some of the local restaurants, Captain Pat's Seafood and Tacos Haciendas."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (64)
"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.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (43)
"Fantastic property! Welcoming, good amenities, accommodating host, and comfortable with amazing views. Will definitely stay here again!"
The price is NZ$534
includes taxes & fees
7 May - 8 May
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (46)
"Exactly as described. Appreciated coffee & cream upon arrival too."
The Lazy Crab Beach House - Free beach passes

MOUNT VERNON RETREAT 🌸

9.8 out of 10, Exceptional, (119)
"Hosts were very communicative and helpful! We could not have asked for more perfect hosts. Check in and out were very easy. Beds were all very comfortable. Everything was well-stocked. TV and Internet were great. Plenty of dishes and coffee. Rooms were tastefully decorated but toddler friendly. Location and neighborhood were great, free and easy parking. Our kiddo wants us to buy the place! We hope to stay again. We did not do the wine experience. "
The price is NZ$414
includes taxes & fees
29 Apr - 30 Apr
MOUNT VERNON RETREAT 🌸

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Ritchie, our host was extremely accommodating. Home looked exactly like the pictures. Very clean and comfortable. Water front! Many good restaurants within walking distance."
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (174)
"The views are fantastic. Very quiet neighborhood. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (113)
"This place was a wonderful spot for our family to have a long weekend getaway. It's on a bluff right next to the ocean with a glorious view and a stairway access to the beach. The beds are comfortable, the house has lots of great spaces to relax or play games, and the beach is a wonderful space to explore, find seashells and possibly a fossil sharks tooth (we had no luck there, but we did find a whale vertebrae, so that's something!). But in any event, we highly recommend! "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.0 out of 10, Wonderful, (2)
"Sweet little place on the water. Quiet neighborhood. Quick trip to campus."
Screened Patio, Deck & Grill: Saint Inigoes Home!

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (19)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway

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.

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

10.0 out of 10, Exceptional, (1)
"The house was close to family in the area, so location was great. The house was clean and airy. The door lock was a bit tricky - otherwise all was excellent."
The price is NZ$562
includes taxes & fees
28 Apr - 29 Apr
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
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.
Don't see what you're looking for?
See all available properties in Southern Maryland
Save an average of 15% on thousands of hotels when you're signed in

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

Gaylord National Resort & Convention Center

4.0 star property
8.6 out of 10, Excellent, (1014)
"This was a wonderful experience. We ate in the hotel. The pool was nice especially for the kids. With the Ferris wheel there it was a nice addition with the VIP paw."
The price is NZ$542
includes taxes & fees
26 Apr - 27 Apr
Gaylord National Resort & Convention Center

Holiday Inn Express Washington DC East - Andrews AFB by IHG

2.5 star property
8.0 out of 10, Very good, (1008)
"The property can benefit from renovations. The room’s A/C system can definitely be modernized. The staff is very good and friendly, trying to help. Breakfast was continental and okay but for the price, it is quite far from Washington, 27-38 minutes drive from the national mall."
The price is NZ$215
includes taxes & fees
18 Apr - 19 Apr
Holiday Inn Express Washington DC East - Andrews AFB by IHG

Holiday Inn Express Waldorf by IHG

2.5 star property
8.2 out of 10, Very good, (900)
"Didn't like the entrance have to always uturn to get to it."
The price is NZ$202
includes taxes & fees
11 May - 12 May
Holiday Inn Express Waldorf by IHG
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.