St. Mary's County Holiday Rentals

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Our top choices for St. Mary's County holiday rentals

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (14 reviews)
"Hosts were very helpful. The cottage is adorable and well maintained. "
United States
William L.
The price is NZ$750
includes taxes & fees
2 June - 3 June
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
Lexington Park
10.0 out of 10, Exceptional, (9 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is NZ$649
includes taxes & fees
2 June - 3 June
Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (4 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 NZ$974
includes taxes & fees
4 June - 5 June
Charming Waterfront 3-bedroom house in Piney Point

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

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is NZ$883
includes taxes & fees
2 June - 3 June
Anne & Fred`s Leonardtown Home W/ Arcade room!

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is NZ$825
includes taxes & fees
2 June - 3 June
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

1 bedroom in a basement with private Private bathroom with cool AC

1 bedroom in a basement with private Private bathroom with cool AC
Waldorf
The price is NZ$108
includes taxes & fees
3 June - 4 June
1 bedroom in a basement with private Private bathroom with cool AC

Rest & Recharge, A-frame Cabin on Winery Grounds

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (64 reviews)
"Always a great stay! "
United States
Amy H.
The price is NZ$457
includes taxes & fees
7 June - 8 June
Rest & Recharge, A-frame Cabin on Winery Grounds

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (51 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is NZ$499
includes taxes & fees
2 June - 3 June
Soul Oasis - home on the Chesapeake Bay

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is NZ$536
includes taxes & fees
2 June - 3 June
Coles Point Marina

Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (1 review)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is NZ$409
includes taxes & fees
7 June - 8 June
Tangier Escape, great place get away from it all on Deal Island, MD.

Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit
Reedville
9.6 out of 10, Exceptional, (20 reviews)
"Great place "
United States
Myranda R.
The price is NZ$452
includes taxes & fees
9 June - 10 June
Newly updated 3 bedroom cottage with Solo Stove fire pit

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, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is NZ$443
includes taxes & fees
2 June - 3 June
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Hague
The price is NZ$332
includes taxes & fees
2 June - 3 June
Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Belle Haven - High Speed internet, walk to town

Belle Haven - High Speed internet, walk to town
Kilmarnock
10.0 out of 10, Exceptional, (34 reviews)
"Great property for small family, stayed here multiple times. "
United States
Lawrence D.
The price is NZ$499
includes taxes & fees
2 June - 3 June
Belle Haven - High Speed internet, walk to town

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (59 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is NZ$434
includes taxes & fees
3 June - 4 June
Deal Island Bay Cottage

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (23 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is NZ$697
includes taxes & fees
8 June - 9 June
Walk to Beach! King Bed & Free Beach Passes

Sail Away

Sail Away
Colonial Beach
9.8 out of 10, Exceptional, (10 reviews)
"Stay was wonderful!"
United States
Karen H.
The price is NZ$577
includes taxes & fees
4 June - 5 June
Sail Away

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Excellent property, excellent host. This is a very well-appointed property located very close to the ferry dock. Golf cart, bikes, and kayaks were in great shape. Chris could not have been a more responsive or helpful host."
United States
Timothy S.
The price is NZ$538
includes taxes & fees
2 June - 3 June
Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
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 St. Mary's County Hotel Reviews

Find out more about St. Mary's County

Everything you need to know about St. Mary's County 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 St. Mary's County 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 St. Mary's County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

St. Mary's County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in St. Mary's County. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A St. Mary's County 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 St. Mary's County holiday rentals we have selected for you start as low as NZ$443 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on St. Mary's County rentals

At Expedia, we put the best St. Mary's County 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 St. Mary's County 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 St. Mary's County 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 St. Mary's County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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