St. Mary's County holiday homes

We found 514 holiday rentals — enter your dates for availability
Select from 70 homes, 38 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 Bookabach

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

Showing deals for:15 Jan - 22 Jan

Exterior
Property grounds
Dining
Marina
Exceptional
(9 reviews)

Houseboat on Solomons Island

Solomons

8% off
NZ$4,022
for 7 nights, 1 houseboat
NZ$575 per night
includes taxes & fees
Houseboat on Solomons Island
Exterior
Living area
Outdoor dining
Private kitchen
Exceptional
(23 reviews)

Bayview Breeze w/screened porch

Colonial Beach

8% off
NZ$5,192
for 7 nights, 1 home
NZ$742 per night
includes taxes & fees
Bayview Breeze w/screened porch
Dine with panoramic waterfront views—perfect for unforgettable group meals
Wake up to serene water views from the primary suite
Enjoy morning coffee or evening drinks on the private waterfront deck
Private waterfront setting with direct access to the shoreline
Exceptional
(22 reviews)

Chesapeake Bay Waterfront Retreat • 7BR • Sleeps 14 • 2 Homes in 1

Scotland

8% off
NZ$9,535
for 7 nights, 1 home
NZ$1,362 per night
includes taxes & fees
Chesapeake Bay Waterfront Retreat • 7BR • Sleeps 14 • 2 Homes in 1
Interior
Outdoor dining
Living area
Interior
Exceptional
(7 reviews)

Driftwood Haven, Chesapeake Bay views throughout

Lusby

12% off
NZ$5,785
for 7 nights, 1 home
NZ$826 per night
includes taxes & fees
Driftwood Haven, Chesapeake Bay views throughout
Room
Private kitchen
Dining
Exterior detail
Exceptional
(25 reviews)

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

Piney Point

7% off
NZ$5,526
for 7 nights, 1 home
NZ$789 per night
includes taxes & fees
WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT
Main Living Room Area with sliding glass doors to deck  -> yard -> beach -> water!
Stove top with a View !
Foosball table for rainy days
View after walking in front door, round table for extra seating, game play
Exceptional
(42 reviews)

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

Ophelia

8% off
NZ$6,833
for 7 nights, 1 home
NZ$976 per night
includes taxes & fees
Pine Shore Beach House on Chesapeake Bay w/ 170ft pier
Exterior
White sand beach
Exterior
Dining
Exceptional
(61 reviews)

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

Montross

8% off
NZ$10,709
for 7 nights, 1 home
NZ$1,530 per night
includes taxes & fees
Beach & River Retreat. Spectacular house with private sand beach and hot tub!
Property grounds
Exterior
Living area
Property grounds
Wonderful
(17 reviews)

Magnificent Water Front Property

Solomons

7% off
NZ$10,300
for 7 nights, 1 home
NZ$1,471 per night
includes taxes & fees
Magnificent Water Front Property
Exterior
Sunrise on your private beach
Exterior
Aerial view
Exceptional
(39 reviews)

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

Hague

7% off
NZ$5,656
for 7 nights, 1 home
NZ$808 per night
includes taxes & fees
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
A view of the livingroom from the kitchen.
From the livingroom, enjoy a sunrise view over the river!
Twin bedroom at front of house.
Dining area
Exceptional
(90 reviews)

Great River Views, walk to Beach !

Colonial Beach

8% off
NZ$5,044
for 7 nights, 1 home
NZ$721 per night
includes taxes & fees
Great River Views, walk to Beach !
Games room
Dining
Living area
Exterior
Exceptional
(6 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
NZ$7,712
for 7 nights, 1 home
NZ$1,102 per night
includes taxes & fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Exterior
entryway
loft bedroom
dining area
Exceptional
(66 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
NZ$2,482
for 7 nights, 1 cottage
NZ$355 per night
includes taxes & fees
Soul Oasis - home on the Chesapeake Bay
Dining
Property grounds
Room
Exterior
Exceptional
(25 reviews)

Breton Bay Family Getaway

Leonardtown

10% off
NZ$8,019
for 7 nights, 1 home
NZ$1,146 per night
includes taxes & fees
Breton Bay Family Getaway
Room
Property grounds
Beach
Miscellaneous
Wonderful
(15 reviews)

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

Benedict

8% off
NZ$2,861
for 7 nights, 1 cottage
NZ$409 per night
includes taxes & fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Propane fire table
Dining area
View of front of stand alone house - note parking under cover for 2-4 cars
View of kitchen dining living
Exceptional
(17 reviews)

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

Colonial Beach

8% off
NZ$4,205
for 7 nights, 1 home
NZ$601 per night
includes taxes & fees
Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub
Kitchen
Exterior
Dining Room
Terrace/patio
Exceptional
(39 reviews)

Waterfront Rivah Home with Free EV Charging On Property

Heathsville

8% off
NZ$6,952
for 7 nights, 1 home
NZ$993 per night
includes taxes & fees
Waterfront Rivah Home with Free EV Charging On Property
Looking from kitchen and dining room to the primary bedroom.
Deck view at dusk.
Dining room
A wall of windows in main living area offers stunning panoramic Potomac views.
Exceptional
(18 reviews)

Water's Edge Cottage -- Luxury Retreat -- 180 Degree Potomac Views

Leonardtown

8% off
NZ$5,719
for 7 nights, 1 home
NZ$817 per night
includes taxes & fees
Water's Edge Cottage -- Luxury Retreat -- 180 Degree Potomac Views
Private kitchen
Interior
Exterior
Living area
Exceptional
(39 reviews)

Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly

Colonial Beach

8% off
NZ$4,243
for 7 nights, 1 home
NZ$606 per night
includes taxes & fees
Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly
Beach
Exterior
Beach
Beach
Exceptional
(48 reviews)

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

Montross

7% off
NZ$4,006
for 7 nights, 1 home
NZ$572 per night
includes taxes & fees
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Exterior
Outdoor dining
Exterior detail
Outdoor dining
Exceptional
(175 reviews)

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

St. Leonard

6% off
NZ$2,624
for 7 nights, 1 cottage
NZ$375 per night
includes taxes & fees
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
Kitchen and Dining Area
Kitchen view of dining room & sitting area
Lounge chairs for catching rays
Entry way and steps to beds & baths
Exceptional
(101 reviews)

Inviting and Serene Home on Monroe Bay Creek

Colonial Beach

12% off
NZ$4,576
for 7 nights, 1 home
NZ$654 per night
includes taxes & fees
Inviting and Serene Home on Monroe Bay Creek
Room
Living area
View of parking pad 1 car is  backed in and 1 for studio on the bay pulled in.
Private kitchen
Exceptional
(31 reviews)

Studio on the Bay.

St. Leonard

8% off
NZ$2,168
for 7 nights, 1 apartment
NZ$310 per night
includes taxes & fees
Studio on the Bay.
Launch your day from the dock on the Bay and choose your adventure: kayak, canoe, paddleboard, sail, or swim. The water is part of your Montross vacation, not a drive away.
Gather everyone outside for dinner, a grill session, or a little friendly competition. Keep the water in sight while you eat, talk, play, and make the most of your Northern Neck getaway.
Slow the morning down with coffee, a puzzle, or a long conversation while you watch the water. Use this area to reconnect before the next round of fun at Easthaven.
Walk down to the dock and choose your next move: swim, fish, launch a boat, or simply watch the water. At Easthaven, your next waterfront adventure is only a few steps away.
Exceptional
(40 reviews)

Waterfront Reset: Views, Games, Boats & Total Calm

Montross

8% off
NZ$4,807
for 7 nights, 1 home
NZ$687 per night
includes taxes & fees
Waterfront Reset: Views, Games, Boats & Total Calm
Room
Property grounds
Interior
Private kitchen
Wonderful
(8 reviews)

Windswept Getaway

Newburg

9% off
NZ$3,914
for 7 nights, 1 cottage
NZ$559 per night
includes taxes & fees
Windswept Getaway

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:

  • Breton Bay Golf Course (2.3 mi / 3.7 km)
  • Maryland International Raceway (13 mi / 21 km)
  • Budds Creek Motocross Park (13.3 mi / 21.5 km)
  • Michael P. O'Brien Athletics and Recreation Center (13.4 mi / 21.6 km)
  • Running Hare Vineyard (15.1 mi / 24.3 km)
  • Ingleside Vineyards (21.8 mi / 35.1 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)
  • Three Notch Park (5.3 mi / 8.5 km)
  • Piney Point Beach (12.2 mi / 19.6 km)
  • Flag Ponds Nature Park (14.4 mi / 23.2 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, Bookabach 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 Bookabach 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, Bookabach 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 Bookabach 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 Bookabach, 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 Bookabach holiday properties may also offer weekly or monthly discounts, so you can stay even longer for less.

More holiday ideas