A white building with a red roof and a lighthouse tower, surrounded by tall grass and under a cloudy sky.

St. Mary's County holiday rentals

We found 518 holiday rentals — enter your dates for availability

Select from 71 homes, 40 cottages and other holiday rentals in St. Mary's County to find one that's perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Popular St. Mary's County destinations on Stayz

A sunset over a calm body of water with a bridge in the foreground.

California

A calm lake with a clear sky and trees on the right.

Lexington Park

A lighthouse and a historic building with a porch, surrounded by a grassy area and trees.

Piney Point

A lakeside view with trees, a wooden dock, and a small shed.

Leonardtown

A river with boats, surrounded by autumn-colored trees and a bridge in the distance.

Mechanicsville

An aerial view of a golf course surrounded by a lake and forested areas.

Ridge

Holiday rentals with weekly discounts – St. Mary's County

Showing deals for:13 Nov - 20 Nov

Exceptional

(8 reviews)

Houseboat on Solomons Island

Solomons

8% off

AU$3,166

for 7 nights, 1 houseboat

AU$452 per night

includes taxes & fees

View after walking in front door, round table for extra seating, game play

Main Living Room Area with sliding glass doors to deck -> yard -> beach -> water!

Exceptional

(41 reviews)

Pine Shore Beach House on Chesapeake Bay w/ 170ft pier

Ophelia

8% off

AU$5,486

for 7 nights, 1 home

AU$784 per night

includes taxes & fees

Wake up to serene water views from the primary suite

Dine with panoramic waterfront views—perfect for unforgettable group meals

Enjoy morning coffee or evening drinks on the private waterfront deck

Exceptional

(20 reviews)

🏖Chesapeake Bay Retreat – Private Beach • Fire Pit • WiFi • 2 Homes in 1

Scotland

8% off

AU$7,628

for 7 nights, 1 home

AU$1,090 per night

includes taxes & fees

Exceptional

(38 reviews)

Waterfront Rivah Home with Free EV Charging On Property

Heathsville

8% off

AU$7,695

for 7 nights, 1 home

AU$1,099 per night

includes taxes & fees

Exceptional

(24 reviews)

WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT

Piney Point

7% off

AU$5,515

for 7 nights, 1 home

AU$788 per night

includes taxes & fees

Exceptional

(9 reviews)

An amazing large group vacation home with elevator and breathtaking views.

Montross

8% off

AU$10,657

for 7 nights, 1 home

AU$1,522 per night

includes taxes & fees

The front porch has ceiling fans to help keep you cool.

Enjoy water views from the dining room and kitchen.

Exceptional

(54 reviews)

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

Fishing Creek

7% off

AU$1,917

for 7 nights, 1 home

AU$274 per night

includes taxes & fees

Exceptional

(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off

AU$4,981

for 7 nights, 1 home

AU$712 per night

includes taxes & fees

Exceptional

(58 reviews)

Beach & River Retreat. Spectacular house with private sand beach and hot tub!

Montross

8% off

AU$7,706

for 7 nights, 1 home

AU$1,101 per night

includes taxes & fees

Exceptional

(5 reviews)

Driftwood Haven, Chesapeake Bay views throughout

Lusby

12% off

AU$4,553

for 7 nights, 1 home

AU$650 per night

includes taxes & fees

Exceptional

(35 reviews)

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Hague

7% off

AU$3,690

for 7 nights, 1 home

AU$527 per night

includes taxes & fees

Exceptional

(56 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off

AU$1,879

for 7 nights, 1 cottage

AU$268 per night

includes taxes & fees

Exceptional

(61 reviews)

Quaint fishing retreat on the lower Potomac Piney Pt

Piney Point

9% off

AU$1,979

for 7 nights, 1 home

AU$283 per night

includes taxes & fees

Great kitchen for entertaining and gathering

Game table to enjoy the board games, backgammon, chess, cards and more

Exceptional

(32 reviews)

Stunning Water Front Home with Private Dock and Beach and Sunsets

Lusby

7% off

AU$5,059

for 7 nights, 1 home

AU$723 per night

includes taxes & fees

Exceptional

(44 reviews)

The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.

Montross

7% off

AU$2,730

for 7 nights, 1 home

AU$390 per night

includes taxes & fees

Kitchen view of dining room & sitting area

Exceptional

(95 reviews)

Inviting and Serene Home on Monroe Bay Creek

Colonial Beach

13% off

AU$3,891

for 7 nights, 1 home

AU$556 per night

includes taxes & fees

Open floor plan, dining table and sleep sofa

Exceptional

(28 reviews)

Quiet Woodland cottage near St. Leonard's Creek

Lusby

7% off

AU$1,168

for 7 nights, 1 cottage

AU$167 per night

includes taxes & fees

Wonderful

(8 reviews)

Windswept Getaway

Newburg

9% off

AU$3,081

for 7 nights, 1 cottage

AU$440 per night

includes taxes & fees

Community pool and putting green and firepits

View of front of stand alone house - note parking under cover for 2-4 cars

Exceptional

(14 reviews)

Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub

Colonial Beach

8% off

AU$3,803

for 7 nights, 1 home

AU$543 per night

includes taxes & fees

Exceptional

(14 reviews)

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

Benedict

8% off

AU$2,295

for 7 nights, 1 cottage

AU$328 per night

includes taxes & fees

Exceptional

(7 reviews)

Charming Duplex in the heart of Leonardtown

Leonardtown

14% off

AU$2,233

for 7 nights, 1 home

AU$319 per night

includes taxes & fees

Gather around the table for family dinner.

Every sunrise brings new hope for a brighter future.

Star light, star bright, first star I see tonight.

Exceptional

(52 reviews)

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek

8% off

AU$2,811

for 7 nights, 1 cottage

AU$402 per night

includes taxes & fees

Exceptional

(15 reviews)

Solomons Island with views of harbor!

Solomons

8% off

AU$2,146

for 7 nights, 1 apartment

AU$307 per night

includes taxes & fees

A quiet and relaxing road with an abundance of deer, birds, squirrels, and crab.

Piney Point Light House and underwater park with German U-Boat is 5 miles away.

A dining room table expands to 12 seats with a view. Two extensions not show.

There is extra bedding for each room and it is all washed between each guest.

Exceptional

(66 reviews)

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

Tall Timbers

16% off

AU$2,072

for 7 nights, 1 cottage

AU$296 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - St. Mary's County

Premier Host

Waterfront Relaxing Getaway

Sleeps 8 · 4 bedrooms · 1+ bathroom

Premier Host

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

Sleeps 6 · 3 bedrooms · 2 bathrooms

Potomac River Getaway at McKays Beach

Sleeps 6 · 2 bedrooms · 1 bathroom

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

Sleeps 16 · 7 bedrooms · 6 bathrooms

Premier Host

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

Sleeps 8 · 3 bedrooms · 1 bathroom

Premier Host

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

Sleeps 10 · 4 bedrooms · 2 bathrooms

Choose a holiday rental for your St. Mary's County getaway

Learn about the unique charm of St. Mary's County with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around St. Mary's County

Are you hoping to find attractions to see while you're in town? Venture out of your cosy holiday rental and experience everything that makes St. Mary's County a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

Maryland International Raceway (13 mi / 21 km)
Running Hare Vineyard (15.1 mi / 24.3 km)
Ingleside Vineyards (21.8 mi / 35.1 km)
White Plains Golf Course (25.1 mi / 40.4 km)
Chesapeake Beach Water Park (28.2 mi / 45.4 km)
Breton Bay Golf Course (2.3 mi / 3.7 km)

Exploring the natural landscape of St. Mary's County

Whether you're looking for adventure or just want to take in the scenery, St. Mary's County is a great place to spend some time outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

St. Mary's River State Park (5.1 mi / 8.2 km)
Piney Point Beach (12.2 mi / 19.6 km)
Flag Ponds Nature Park (14.4 mi / 23.2 km)
Saint George Island Beach (14.6 mi / 23.6 km)
Cove Point Beach (14.8 mi / 23.9 km)
Matoaka Beach (15 mi / 24.2 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in St. Marys County?

Houses are the most popular type of holiday home in St. Marys County, according to our data. Even if you've got a different idea about what you want, Stayz has properties in a variety of shapes and sizes. Filter our options to find your ideal match.

How much does it cost to rent a holiday home in St. Marys County?

A number of things influence the price of a holiday home in St. Marys County, such as the type of property, season and length of stay. But, all of our holiday homes have something in common — excellent value. Just enter your travel dates to find your perfect fit.

How much does it cost to rent a beach house in St. Marys County?

The average price for a holiday home near the beach in St. Marys County will depend on when you're going and the size and style of property you're looking for. You can easily find prices on Stayz by entering your preferred travel dates. Then use our filter tool to choose the number of bedrooms and amenities that you prefer, such as WiFi, a pool and air conditioning.

What are popular home amenities in St. Marys County?

Some of the most popular home amenities people search for in St. Marys County include a fridge, a microwave oven and off-street parking options. Whether you're travelling with friends, family or even pets, Stayz holiday properties have the best amenities for beginning new traditions with the people that matter most.

Are there large group holiday homes in St. Marys County?

St. Marys County has 17 holiday homes that can host 10 or more guests. These stays come with the space you need to enjoy good times with loved ones.

What are the top attractions for families in St. Marys County?

Keeping the kids entertained during your stay in St. Marys County is simple with these exciting family-friendly attractions:

Budds Motorcross Speedway
Maryland International Raceway
Point Lookout State Park

Can I find two-bedroom holiday homes in St. Marys County?

Take your pick of 15 two-bedroom holiday properties in St. Marys County. Put the kids in the second room or fill it with a couple of your nearest and dearest friends. There's enough space for whoever's fortunate enough to be coming along for the ride.

Are there holiday homes with WiFi in St. Marys County?

Whether you want to keep up with world events, check emails or surf social media, there are 33 holiday homes with WiFi in St. Marys County. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.

How old do you have to be to rent a holiday home in St. Marys County?

The minimum age is generally 16, 18 or 21. It can change across properties on Stayz, so look at the rules of your preferred St. Marys County stay before making a booking.

How long can I rent a holiday home in St. Marys County for?

The amount of time you can rent a St. Marys County holiday home for is up to each property. Simply put in your preferred travel dates to view options offering extended stays. They feature all you require to make your extended holiday more convenient and enjoyable, such as laundries and air conditioning. Some Stayz holiday properties may also offer weekly or monthly discounts, so you can stay even longer for less.

More holiday ideas

Holiday homes