Southern Maryland holiday homes

We found 1,688 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southern Maryland

Showing deals for:13 Nov - 20 Nov

Upstairs Hall
Porch Dining Table
Swimming Pool
Kitchen
Exceptional
(33 reviews)

Waterfront Home near Annapolis, MD

Galesville

8% off
NZ$22,911
for 7 nights, 1 home
NZ$3,273 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Dining
Property grounds
Room
Exterior
Exceptional
(8 reviews)

Houseboat on Solomons Island

Solomons

8% off
NZ$3,832
for 7 nights, 1 houseboat
NZ$547 per night
includes taxes & fees
Houseboat on Solomons Island
Room
Property grounds
Living area
Beach
Exceptional
(92 reviews)

Chesapeake Bay Cottage

Churchton

8% off
NZ$4,193
for 7 nights, 1 cottage
NZ$599 per night
includes taxes & fees
Chesapeake Bay Cottage
Living Room into Kitchen/Dining
Foyer into Living Room
Kitchen/dining
Foyer with stairs to second floor peak into 1st  floor master bedroom
Exceptional
(90 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
NZ$7,420
for 7 nights, 1 home
NZ$1,060 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Enjoy morning coffee or evening drinks on the private waterfront deck
Wake up to serene water views from the primary suite
Interior
Private waterfront setting with direct access to the shoreline
Exceptional
(21 reviews)

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

Scotland

8% off
NZ$9,351
for 7 nights, 1 home
NZ$1,336 per night
includes taxes & fees
🏖Chesapeake Bay Retreat – Private Beach • Fire Pit • WiFi • 2 Homes in 1
Living area
Room
Private kitchen
Living area
Exceptional
(9 reviews)

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

Montross

7% off
NZ$13,767
for 7 nights, 1 home
NZ$1,967 per night
includes taxes & fees
An amazing large group vacation home with elevator and breathtaking views.
Living area with sold out couch
Marina
Property grounds
Eat in at kitchen table
Exceptional
(13 reviews)

Gem on the Potomac River! Private beach, local restaurant, beautiful sunsets!

King George

8% off
NZ$2,789
for 7 nights, 1 cottage
NZ$398 per night
includes taxes & fees
Gem on the Potomac River! Private beach, local restaurant, beautiful sunsets!
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
Delightful front garden welcomes you when approaching house from driveway
Convenient open-concept design:  kitchen, dining and living areas
Exceptional
(161 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
NZ$3,776
for 7 nights, 1 home
NZ$539 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Dining
Private kitchen
Room
Interior
Exceptional
(24 reviews)

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

Piney Point

7% off
NZ$6,651
for 7 nights, 1 home
NZ$950 per night
includes taxes & fees
WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT
Two bar stools are available at the kitchen bar.
The front porch has ceiling fans to help keep you cool.
Exterior
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
NZ$2,268
for 7 nights, 1 home
NZ$324 per night
includes taxes & fees
Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly
Exterior
Dining
Games room
Living area
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
NZ$5,899
for 7 nights, 1 home
NZ$843 per night
includes taxes & fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Living area
Outdoor dining
Living area
Interior
Exceptional
(5 reviews)

Driftwood Haven, Chesapeake Bay views throughout

Lusby

12% off
NZ$5,514
for 7 nights, 1 home
NZ$788 per night
includes taxes & fees
Driftwood Haven, Chesapeake Bay views throughout
Coles Point Tavern. Go by boat
Property grounds
Room
Living area
Exceptional
(35 reviews)

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

Hague

7% off
NZ$4,556
for 7 nights, 1 home
NZ$651 per night
includes taxes & fees
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Dining Room - Seats 6
View down the lane
Sit and stay a while!
Living Room with flat screen TV and sleeper sofa
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
NZ$3,409
for 7 nights, 1 cottage
NZ$487 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Interior
Living area
Living area
Private kitchen
Wonderful
(12 reviews)

Posh House Near DC MGM National Harbor

Alexandria

8% off
NZ$5,316
for 7 nights, 1 home
NZ$759 per night
includes taxes & fees
Posh House Near DC MGM National Harbor
loft bedroom
entryway
dining area
steps to the loft
Exceptional
(56 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
NZ$2,278
for 7 nights, 1 cottage
NZ$325 per night
includes taxes & fees
Soul Oasis - home on the Chesapeake Bay
Fifth Bedroom
Upstairs Living Room
Interior
Deck
Exceptional
(50 reviews)

Serene Cave in Stafford, Va

Stafford

7% off
NZ$4,276
for 7 nights, 1 home
NZ$611 per night
includes taxes & fees
Serene Cave in Stafford, Va
Dining
Exterior
Property grounds
Property grounds
Wonderful
(17 reviews)

Magnificent Water Front Property

Solomons

7% off
NZ$9,831
for 7 nights, 1 home
NZ$1,404 per night
includes taxes & fees
Magnificent Water Front Property
Private kitchen
Pool
Private kitchen
Property grounds
Exceptional
(95 reviews)

Large Heated Pool & Hot Tub, Near Quantico DAY Parties and Cookouts Welcome

Stafford

7% off
NZ$3,559
for 7 nights, 1 home
NZ$508 per night
includes taxes & fees
Large Heated Pool & Hot Tub, Near Quantico DAY Parties and Cookouts Welcome
Dining Room
Entrance
Exterior
Basement
Exceptional
(81 reviews)

Townhouse with great value

Stafford

7% off
NZ$3,581
for 7 nights, 1 home
NZ$512 per night
includes taxes & fees
Townhouse with great value
Exterior detail
Be ready to float! Bring your own inner tubes  and tennis shoes!
Living area
Living area
Exceptional
(143 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
NZ$3,521
for 7 nights, 1 cottage
NZ$503 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Private kitchen
Room
Living area
Dining
Exceptional
(13 reviews)

Clover Cottage - 6BR 4Bath Getaway in Old Town

Alexandria

7% off
NZ$9,102
for 7 nights, 1 cottage
NZ$1,300 per night
includes taxes & fees
Clover Cottage - 6BR 4Bath Getaway in Old Town
Marina
St George's Island
Property grounds
Interior
Exceptional
(61 reviews)

Quaint fishing retreat on the lower Potomac Piney Pt

Piney Point

9% off
NZ$2,399
for 7 nights, 1 home
NZ$343 per night
includes taxes & fees
Quaint fishing retreat on the lower Potomac Piney Pt
Hallway to bedroom: a look from the entrance door
Bright and open living room, connected to dining room, a view from the entrance
Living room, bright and open, new and stylish furniture and original artwork
Gourmet kitchen for those who hope to cook or whip up a quick breakfast
Exceptional
(46 reviews)

Modern 3BR/2BA, Free parking, 9 miles to DC, minutes to 395-495

Alexandria

7% off
NZ$3,452
for 7 nights, 1 home
NZ$493 per night
includes taxes & fees
Modern 3BR/2BA, Free parking, 9 miles to DC, minutes to 395-495
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Take in the waterfront beauty of Southern Maryland

Enjoy the live music and other features of Southern Maryland. This city's sporting events, boating and shopping draw many visitors. 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 Southern Maryland

Are you looking for attractions to visit while you're in town? Venture out of your holiday home and experience everything that makes Southern Maryland a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Running Hare Vineyard (5.9 mi / 9.5 km)
  • Maryland International Raceway (9.4 mi / 15.1 km)
  • White Plains Golf Course (11.3 mi / 18.2 km)
  • Chesapeake Beach Water Park (16.4 mi / 26.3 km)
  • Thanksgiving Farm Wines (25.4 mi / 40.9 km)
  • Renditions Golf Club (27.6 mi / 44.5 km)

Exploring the natural features in Southern Maryland

Whether you're looking for adventure or just want to appreciate the scenery, Southern Maryland is a great place to spend some time outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Matoaka Beach (13.9 mi / 22.4 km)
  • Breezy Point Beach (14 mi / 22.5 km)
  • Thomas Stone National Historic Site (16.7 mi / 26.8 km)
  • St. Mary's River State Park (19.9 mi / 32 km)
  • Cove Point Beach (20.7 mi / 33.3 km)
  • Colonial Beach (21.9 mi / 35.3 km)

Frequently asked questions

What is the best area to stay in Southern Maryland when booking a holiday home?
One of the most sought-after destinations to choose your Bookabach holiday home in Southern Maryland is Fort Washington. Base yourself here and explore its must-see attractions, including Fort Washington Park and Fort Washington Marina.
What is the most popular type of holiday home accommodation in Southern Maryland?
Based on our data, houses are the most in-demand holiday home type in Southern Maryland. But that goes without saying, everyone's idea of the perfect trip isn't going to be the same. Bookabach has holiday homes of all shapes, sizes and budgets, so you're bound to find the perfect match.
How much does it cost to rent a holiday home in Southern Maryland?
Season, property type and length of stay are some things that can affect the price of a holiday home. Simply click on your travel dates to find your ideal match. From homey country cottages to expansive villas, all Bookabach holiday homes offer incredible value.
How much does it cost to rent a beach house in Southern Maryland?
When you travel and the style and size of the property will help determine the cost of your beachside stay. Put in your Southern Maryland travel dates to see your options on Bookabach. Did someone just say "private pool"? Use our filters to select the amenities and features you want in your beach house.
What are popular home amenities in Southern Maryland?
A fridge, a microwave oven and off-street parking options head the list of most popular home amenities in Southern Maryland. Whether you plan to go on your own, with your significant other or as a family, Bookabach can help you find a holiday home that suits your tastes with all the features you'll enjoy.
Are there large group holiday homes in Southern Maryland?
Southern Maryland has 33 holiday homes that can cater to 10 or more guests. These properties come with the space you need to enjoy good times with loved ones.
What are the top attractions for families in Southern Maryland?
Keep the kids busy at these top family-friendly attractions in Southern Maryland:
  • Calvert Cliffs State Park
  • St. Charles Towne Centre
  • Chesapeake Beach Water Park
Can I find two-bedroom holiday homes in Southern Maryland?
Choose from 45 two-bedroom properties in Southern Maryland. Give the kids the second room or fill it with a couple of your favourite people. There's plenty of space for whoever's lucky enough to be coming along for the ride.
Are there holiday homes with WiFi in Southern Maryland?
You can pick from 112 holiday homes with WiFi in Southern Maryland. If you'd like to disconnect from the world during your trip, but still need to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How old do you have to be to rent a holiday home in Southern Maryland?
The minimum age permitted can vary across properties on Bookabach, so look at the rules of the holiday home in Southern Maryland you're interested in. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Southern Maryland for?
It really depends on the Southern Maryland property. To look at a list of options offering extended stays, simply enter your dates and number of guests into the Bookabach search page. You can enjoy having the property to yourself, as well as comforts such as a full kitchen, air conditioning and a backyard where the little ones can play. Keep an eye out for long-term stays that offer weekly or monthly discounts.

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