Southern Maryland Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
18 Oct - 19 Oct
Tomorrow
19 Oct - 20 Oct
Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov

Holiday Rentals in Southern Maryland

Outdoor dining
The Cozy Crab- Your Charming Haven in Lovely North Beach!
The Cozy Crab- Your Charming Haven in Lovely North Beach!
9.8 out of 10, Exceptional, (11)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
United States
scott
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (50)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
United States
Lynne J.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Terrace/patio
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Tiny, Funky, and Full of Love - Welcome to the Love Shack
9.8 out of 10, Exceptional, (10)
"Such a great accommodation!!! We were here for a swim meet in town and Katie was the greatest host. We had all the comforts and amenities needed. We will def be staying again. "
United States
Joleen H.
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Terrace/patio
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
9.8 out of 10, Exceptional, (56)
"We had a wonderful experience and stay at this cute little cottage. Hosts were amazing as well. Cottage has everything you need. Cute decor, plenty of cookware, towels, linens, TV with streaming and comfortable couch. Communication with host was outstanding and easy check-in and check-out. Will definitely stay here again and strongly recommend to others as a place to stay in the area."
United States
Mary S.
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (180)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
United States
Michelle R.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Property grounds
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (151)
"The place was great, the host was great,"
United States
Travis
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Interior
Waterfront Solomons Apartment
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (13)
"Very clean, awesome location and amazing hosts!! "
United States
Jeff R.
The price is AU$413
includes taxes & fees
19 Oct - 20 Oct
Waterfront Solomons Apartment
Dining
Million Dollar View of the Chesapeake Bay
Million Dollar View of the Chesapeake Bay
9.8 out of 10, Exceptional, (129)
"We just enjoyed our fourth year at Million Dollar View of the Chesapeake Bay and already look forward to our next vacation at this wonderful home!"
United States
Melissa G.
Million Dollar View of the Chesapeake Bay
Interior
Waterfront Wildlife Retreat on the Patuxent River
Waterfront Wildlife Retreat on the Patuxent River
10.0 out of 10, Exceptional, (171)
"We went here just for a little weekend getaway for my boyfriend, his brother, his brother’s girlfriend and their kids. We had the absolute best time, such a nice getaway even if it was only for 3 days. The view of the bay from the house is gorgeous and everything was perfect. I will be recommending this stay to anyone I can! "
United States
Nicole V.
Waterfront Wildlife Retreat on the Patuxent River
1 bedroom, iron/ironing board, WiFi, bed sheets
National Harbor Suite 2
National Harbor Suite 2
9.0 out of 10, Wonderful, (2)
"It was clean, had a good bed, in a quiet neighborhood. The host was kind and helpful. "
United States
Timothy M.
National Harbor Suite 2
Dining
Waterfront- 5-bedroom house with dock in charming North Beach
Waterfront- 5-bedroom house with dock in charming North Beach
2.0 star property
10.0 out of 10, Exceptional, (2)
"Lovely home with beautiful views of the Bay. Very spacious and well appointed. The hosts were very responsive to our questions. Great place to celebrate our birthdays with all the family including grandkids. Very convenient to North Beach. "
United States
ellen p.
Waterfront- 5-bedroom house with dock in charming North Beach
Marina
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.8 out of 10, Exceptional, (41)
"Perfectly situated on the water for a fair price and plenty of room for me and my husband would recommend to anybody who wants a quiet stay with a amazing view "
United States
Storm H.
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Fridge, microwave, oven, stovetop
Cozy Cottage with access to and partially obstructed views of the bay.
Cozy Cottage with access to and partially obstructed views of the bay.
9.0 out of 10, Wonderful, (30)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
United States
Holly C.
Cozy Cottage with access to and partially obstructed views of the bay.
Beach
Belle of the Chesapeake Bay
Belle of the Chesapeake Bay
9.2 out of 10, Wonderful, (16)
"Excellent communication from the owner, Julie and the property manager. Our family (newborn to adults) stayed at this property while in town for a wedding at Rousby Hall. We were a quick and easy 15 minute drive away from the venue. The house was very clean and nicely set up to accommodate our group. We only wish we had more time to spend at the house than we did. The pictures are exactly what you see when you check in - no unhappy surprises. Thank you for hosting us and being so flexible...
United States
eileen b.
Belle of the Chesapeake Bay
Exterior
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
9.8 out of 10, Exceptional, (76)
"The property is just as listed! Thoroughly enjoyed the house, the grounds, and the beach! Rick was accommodating and responsive. What a great place!"
United States
David and Ilana X.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
On the beach
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.
9.6 out of 10, Exceptional, (5)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
United States
Berenice N.
The price is AU$469
includes taxes & fees
19 Oct - 20 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Terrace/patio
El Camino
El Camino
10.0 out of 10, Exceptional, (49)
"Great location, the dock is perfect for sunsets, nice balance of waterfront but also cabin vibes"
United States
Alan B.
El Camino
Fridge, microwave, oven, stovetop
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
10.0 out of 10, Exceptional, (124)
"Really enjoyed our time here. The outdoor space in the back was great with the swing and the fire pits. Our kids loved walking to the beach everyday and catching crabs. "
United States
David Z.
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Fridge, microwave, oven, stovetop
Sweet Bamboo Beach Cottage
Sweet Bamboo Beach Cottage
9.8 out of 10, Exceptional, (80)
"Cute and clean house..close to beach and restaurants!! We will visit again !"
United States
Deborah O.
Sweet Bamboo Beach Cottage
Terrace/patio
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
10.0 out of 10, Exceptional, (3)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is AU$569
includes taxes & fees
20 Oct - 21 Oct
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southern Maryland Hotel Reviews

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

10/10 Excellent
"Breakfast choices very nice. Room clean, comfy, beautiful view. Staff very pleasant "
Kathleen 1-night trip
Posted 16 hours ago
Solomons Inn Resort & Marina

Find out more about Southern Maryland

Everything you need to know about Southern Maryland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southern Maryland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southern Maryland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southern Maryland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southern Maryland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southern Maryland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southern Maryland holiday rentals we have selected for you start as low as AU$413 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Southern Maryland rentals

At Expedia, we put the best Southern Maryland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southern Maryland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southern Maryland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southern Maryland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia