Vacation Rentals in Southern Maryland

Vacation Rentals in Southern Maryland

Start comparing over 146970 rentals in Southern Maryland and book at the best price!

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Free cancellation
Vacation house
Vacation apartment
Pool
Internet
Pets allowed
4.0
& higher

Popular Vacation Rentals in Southern Maryland

Vacation rental for 2 people, with yard and view in Southern Maryland
from
$238
per night
Vacation rental for 2 people, with yard and view
2 pers.1 bedroom1mi to the beach
FREE cancellation
4.7
(74 reviews)
Vacation rental for 3 people, with view and sauna as well as balcony and pool in Southern Maryland
from
$81
per night
Vacation rental for 3 people, with view and sauna as well as balcony and pool
3 pers.1 bedroom
4.0
(2513 reviews)
Vacation rental for 2 people, with yard and hot tub in Southern Maryland
from
$125
per night
Vacation rental for 2 people, with yard and hot tub
2 pers.1 bedroom5.6mi to the beach
FREE cancellation
4.9
(22 reviews)
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Vacation rentals with free cancellation

Hotel for 2 people, with pool and hot tub, kid friendly in Southern Maryland
from
$96
per night
Hotel for 2 people, with pool and hot tub, kid friendly
2 pers.1 bedroom291ft²7.5mi to the beach
FREE cancellation
4.3
(770 reviews)
Hotel for 4 people, with yard and pool in Southern Maryland
from
$86
per night
Hotel for 4 people, with yard and pool
4 pers.1 bedroom7.6mi to the beach
FREE cancellation
4.6
(242 reviews)
Hotel for 4 people, with pool, kid friendly in Southern Maryland
from
$75
per night
Hotel for 4 people, with pool, kid friendly
4 pers.1 bedroom7.7mi to the beach
FREE cancellation
3.9
(128 reviews)
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Vacation Rentals in Southern Maryland

Vacation rental for 2 people, with terrace in Southern Maryland
from
$107
per night
Vacation rental for 2 people, with terrace
2 pers.1 bedroom
4.1
(15 reviews)
Hotel for 4 people, with pets in Southern Maryland
from
$96
per night
Hotel for 4 people, with pets
4 pers.1 bedroom7.6mi to the beach
4.2
(43 reviews)
Vacation rental for 6 people, with yard and view in Southern Maryland
from
$138
per night
Vacation rental for 6 people, with yard and view
6 pers.2 bedrooms1.8mi to the beach
4.8
(11 reviews)
Vacation rental for 2 people, with terrace and view in Southern Maryland
from
$178
per night
Vacation rental for 2 people, with terrace and view
2 pers.1 bedroom5.3mi to the beach
4.8
(13 reviews)
Vacation rental for 10 people, with balcony and sauna in Southern Maryland
from
$933
per night
Vacation rental for 10 people, with balcony and sauna
10 pers.4 bedrooms6,491ft²5.7mi to the beach
5.0
(9 reviews)
Vacation rental for 8 people, with yard, kid friendly in Southern Maryland
from
$275
per night
Vacation rental for 8 people, with yard, kid friendly
8 pers.3 bedrooms990ft²3.7mi to the beach
5.0
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Pet-friendly Vacation Rentals

Vacation rental for 14 people, with yard and pool, with pets in Southern Maryland
from
$1,982
per night
Vacation rental for 14 people, with yard and pool, with pets
14 pers.7 bedrooms6.9mi to the beach
5.0
(6 reviews)
Vacation rental for 6 people, with yard in Southern Maryland
from
$79
per night
Vacation rental for 6 people, with yard
6 pers.2 bedrooms3,218ft²
4.2
(3 reviews)
Vacation rental for 11 people, with yard and pool, kid friendly in Southern Maryland
from
$433
per night
Vacation rental for 11 people, with yard and pool, kid friendly
11 pers.6 bedrooms3,993ft²6.8mi to the beach
5.0
(5 reviews)
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Vacation Rentals with Pool

Vacation rental for 3 people, with pool in Southern Maryland
from
$183
per night
Vacation rental for 3 people, with pool
3 pers.1 bedroom161ft²
Hotel for 3 people, with pool, kid friendly in Southern Maryland
from
$67
per night
Hotel for 3 people, with pool, kid friendly
3 pers.1 bedroom
3.0
(378 reviews)
Hotel for 3 people, with pool in Southern Maryland
from
$82
per night
Hotel for 3 people, with pool
3 pers.1 bedroom549ft²7.8mi to the beach
4.4
(73 reviews)
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Vacation Rentals with Internet

Hotel for 2 people in Southern Maryland
from
$68
per night
Hotel for 2 people
2 pers.1 bedroom323ft²5.2mi to the beach
3.7
(778 reviews)
Vacation rental for 6 people, with yard, kid friendly in Southern Maryland
from
$205
per night
Vacation rental for 6 people, with yard, kid friendly
6 pers.2 bedrooms4.2mi to the beach
Hotel for 4 people in Southern Maryland
from
$78
per night
Hotel for 4 people
4 pers.1 bedroom323ft²
4.4
(695 reviews)
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Find Vacation Rentals in Southern Maryland

Map

Highlights Southern Maryland

  • Peaceful getaways
  • Authentic food
  • Wide selection of outdoor activities
  • Historical sites
  • Sandy public beaches

Most popular in Southern Maryland

Pool 3
Internet 26
Pets allowed 11
Balcony/Terrace 7
TV 24
Air conditioning 26

Prices and availability

Prices

$550
January
February
March
April
May
Average price per week

Availabilities

64 %
January
February
March
April
May
Percentage of available rentals

Vacation rentals in Southern Maryland

Vacation rentals locations

Would you like to stay away from the big city and visit a peaceful place where you can unwind and be at the center of all fun? Visit Southern Maryland for your next vacation and enjoy staying in a suburban area. Here, you will relax in a serene accommodation and access the best attractions sites for recreation. And the good thing is, you will find most vacation rentals near the shoreline on beaches like Chesapeake, Calvert Beach-Long Beach or North Beach. If you want to stay near historical sites and landmarks, you can look for rentals in the northwestern side of Southern Maryland. Spend your days in your rentals relaxing or go out and soak up what Southern Maryland has to offer.

Peaceful vacation rentals for everyone

The first thing you'll want to consider before visiting Southern Maryland is the condition of the accommodations. If you're going to come with your family, lover or friends, you'd prefer to stay in comfy and spacious rentals. In addition, your wish to stay in rentals with all the amenities you like. Luckily, most rentals here offer you ensures you feel right at home. You'll find rentals with fully equipped kitchens and spacious entertainment areas when you come as a family. Look for child-friendly rentals and allow you to bring your pet along. You can find rentals with a garden, balcony and view. Stay entertained in a rental that offers a pool, internet, and TV.

Vacations in Southern Maryland

The area and getting around

A shoreline bustling with activities

Southern Maryland has a variety of places you can visit to explore and discover what makes it tick among visitors. First, you may opt to visit the three counties in Southern Maryland. These counties include Charles, Calvert and St. Mary's Counties. Other southern portions of Southern Maryland include Prince George's and Anne Arundel. These counties are attached on the Chesapeake Bay's western shore. Here, you can find several public beaches, including the Calvert County Beaches, Chesapeake, and North Beach. You can spend a sunny afternoon on the sandy beaches or enjoy playing in the water.

Southern Maryland towns and communities

If you want to stay out of the water, you can explore various towns and communities in Southern Maryland. It doesn't matter where you stay. You only need to leave your rental in the morning and walk or drive to the towns or communities around when you visit here. Explore around and look for landmarks and historical buildings that attract visitors. Visit the nearby markets and look for antique shops, grocery markets and malls where you can buy a few items. If you want to find out why Southern Maryland food and cuisine is popular, visit restaurants near the shoreline and enjoy the local food and seafood.

Travelers and outdoor activities

Southern Maryland for culture and history buffs

Southern Maryland has a relatively small footprint but is rich in history. You can get a chance to learn the history of the most influential people and events. You can visit various historical sites with your loved ones and learn the history of Southern Maryland. First, head to Charles County and visit The African American Heritage Society and learn about the culture and history of African Americans. You'll understand the contributions of African Americans towards the growth and development of Southern Maryland. Next, visit Chesapeake, where you'll find Bayside History Museum. You'll find various exhibitions and learn about Captain John Smith.

Public beaches for water sports

After spending your morning exploring Southern Maryland towns and communities, you may want to head to the nearest beaches. Southern Maryland has about one thousand miles of shoreline. Here, you can find stunning beaches like North Beach, Calvert Beaches and parks like Flag Ponds Nature Park. You can enjoy relaxing on the sand or join others in water sports such as kayaking, paddleboarding, fishing, trailing, swimming, and shark teeth hunting.

„The early Southern Maryland colony was a tobacco farming colony. However, many settlers died due to diseases until immunities built up.“

Top 5 travel tips for Southern Maryland

Escape route of Lincoln's Assassin

Visit Surratt House Museum and learn about the route that John Wilkes Booth escaped through after he assassinated President Abraham Lincoln. You'll learn about where he stayed in Southern Maryland for two weeks before he was captured and killed. Enjoy learning about the history of Mary Surratt, who hosted Booth in his escape.

Mallows Bay Park to see shipwrecks

Visit Mallows Bay Park in Nanjemoy and explore this National Marine Sanctuary. Then, visit the waters of the Potomac River, where you'll find the World War 1 Ghost Fleet. Enjoy sightseeing and taking pictures of this ship graveyard with a total of more than 200 shipwrecks. You'll find the place ideal for fishing, hiking and wildlife viewing.

Annmarie Sculpture Garden & Arts Center

Do you love art? Visit Solomons Islands, where you can enjoy exploring art buildings. Here, you'll find a variety of exhibitions and ornaments. enjoy an Ornament Show & Sale and a collection like "When Darkness Falls: Night Explorations." This family-friendly art center offers visitors a chance to buy gifts at a gift shop and dine at a café.

Patuxent Wine Trail for wine tasting

Besides enjoying the scenic sites near the Patuxent River, you'll find the best wines on the Eastern Seaboard. Head to Cove Point Winery or Running Hare Vineyard, visit their breathtaking vineyards, and enjoy spectacular views. You can try wines made from Vidal Blanc, Cabernet Franc and Chardonnay grapes.

Calvert Cliffs State Park for fossils finding

Visit Calvert Cliffs State Park and spend time searching for fossils at the enormous cliffs. Enjoy exploring the site that's over 10 million years old with your loved ones. Here. You can find unique fossils and prehistoric remains of sharks, whales, seabirds and rays. In addition, you can enjoy other activities like hiking, picnicking and playing on a sandy beach.

FAQs: Vacation Rentals in Southern Maryland

On average, how much do vacation rentals in Southern Maryland cost?

Southern Maryland is one of the cheapest destinations in the USA. For a stay here you pay around $317.61 per night.

During which months are vacation rentals cheaper in Southern Maryland?

Those who want to save as much as possible travel to Southern Maryland in October, December, and February, the cheapest months of the year, with average prices of $273.35, $280.6, and $288.51 per night, respectively, based on data collected in 2020.

When does the price of vacation rentals in Southern Maryland go up the most?

In 2020, the month that had the highest annual average in Southern Maryland was May, with an average price of $383.96 per night. This was followed by July, with an average of $372.18, and June, with $341.22.

Is Southern Maryland a good location for a last-minute getaway?

It's worthwhile if you can book your stay with plenty of time when visiting Southern Maryland, as only 13 % of our properties are usually available throughout the year.

Which months offer the highest availability?

January, February and December are, in order of highest to lowest, the months that present the largest number of accommodations free, with respective average availability figures of 29.8%, 26.5%, and 25.75%.

How many rentals does Holidu have in Southern Maryland?

We have 70 properties for you in Southern Maryland, provided by our 2 local and international partners.

Holidu compares hundreds of websites to find your perfect holiday rental for the best price.

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