Southern Maryland holiday homes

We found 1,796 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southern Maryland

Showing deals for:1 Jan - 8 Jan

Exterior
Property grounds
Marina
Dining
Exceptional
(9 reviews)

Houseboat on Solomons Island

Solomons

8% off
NZ$4,046
for 7 nights, 1 houseboat
NZ$578 per night
includes taxes & fees
Houseboat on Solomons Island
Upstairs Hall
Porch Dining Table
Exterior Rear of House and Dock
Swimming Pool
Exceptional
(35 reviews)

Waterfront Home near Annapolis, MD

Galesville

8% off
NZ$23,833
for 7 nights, 1 home
NZ$3,405 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
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$9,208
for 7 nights, 1 home
NZ$1,315 per night
includes taxes & fees
Beach & River Retreat. Spectacular house with private sand beach and hot tub!
Living area
Property grounds
Room
Private kitchen
Exceptional
(94 reviews)

Chesapeake Bay Cottage

Churchton

8% off
NZ$4,338
for 7 nights, 1 cottage
NZ$620 per night
includes taxes & fees
Chesapeake Bay Cottage
3rd Bedroom, next to the twin bedroom.
From the livingroom, enjoy a sunrise view over the river!
Great kitchen with views of the river and easy access to outside grill
A view of the livingroom from the kitchen.
Exceptional
(90 reviews)

Great River Views, walk to Beach !

Colonial Beach

8% off
NZ$5,117
for 7 nights, 1 home
NZ$731 per night
includes taxes & fees
Great River Views, walk to Beach !
Pool
The view off of the point, breathtaking.
Another view from above.
Interior
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
NZ$8,531
for 7 nights, 1 home
NZ$1,219 per night
includes taxes & fees
Grandview- Main House
Outdoor dining
Living area
Interior
Exterior
Exceptional
(23 reviews)

Bayview Breeze w/screened porch

Colonial Beach

8% off
NZ$5,146
for 7 nights, 1 home
NZ$735 per night
includes taxes & fees
Bayview Breeze w/screened porch
Exterior
Dining
Terrace/patio
Games room
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
NZ$7,467
for 7 nights, 1 home
NZ$1,067 per night
includes taxes & fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Exterior
Sunrise on your private beach
Exterior
Aerial view
Exceptional
(37 reviews)

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

Hague

7% off
NZ$4,356
for 7 nights, 1 home
NZ$622 per night
includes taxes & fees
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Dining
Private kitchen
Exterior detail
Interior
Exceptional
(24 reviews)

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

Piney Point

7% off
NZ$5,608
for 7 nights, 1 home
NZ$801 per night
includes taxes & fees
WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT
Interior
Outdoor dining
Living area
Interior
Exceptional
(6 reviews)

Driftwood Haven, Chesapeake Bay views throughout

Lusby

12% off
NZ$5,848
for 7 nights, 1 home
NZ$835 per night
includes taxes & fees
Driftwood Haven, Chesapeake Bay views throughout
Interior
Property grounds
Room
Miscellaneous
Wonderful
(15 reviews)

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

Benedict

8% off
NZ$2,820
for 7 nights, 1 cottage
NZ$403 per night
includes taxes & fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Property grounds
Exterior
Property grounds
Living area
Wonderful
(17 reviews)

Magnificent Water Front Property

Solomons

7% off
NZ$10,185
for 7 nights, 1 home
NZ$1,455 per night
includes taxes & fees
Magnificent Water Front Property
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
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
(164 reviews)

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

Sherwood

10% off
NZ$3,985
for 7 nights, 1 home
NZ$569 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Room
vista from the great room!
Interior
view from the pier
Bay is 2 feet deep at stairs
Exceptional
(141 reviews)

Million Dollar View of the Chesapeake Bay

Deale

7% off
NZ$4,595
for 7 nights, 1 home
NZ$656 per night
includes taxes & fees
Million Dollar View of the Chesapeake Bay
Interior
Property grounds
Room
Exterior
Exceptional
(25 reviews)

Breton Bay Family Getaway

Leonardtown

10% off
NZ$7,974
for 7 nights, 1 home
NZ$1,139 per night
includes taxes & fees
Breton Bay Family Getaway
Beach
Exterior
Beach
Beach
Exceptional
(46 reviews)

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

Montross

7% off
NZ$4,124
for 7 nights, 1 home
NZ$589 per night
includes taxes & fees
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Outdoor banquet area
Exterior
view from balcony overlooking playhouse, pergola and Brooks Creek
two twin beds and play area in loft
Exceptional
(276 reviews)

Family and Pet-Friendly, Waterfront with Pier

Cambridge

8% off
NZ$4,025
for 7 nights, 1 cottage
NZ$575 per night
includes taxes & fees
Family and Pet-Friendly, Waterfront with Pier
Exterior detail
Be ready to float! Bring your own inner tubes  and tennis shoes!
Living area
Interior
Exceptional
(144 reviews)

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

Bozman

12% off
NZ$3,663
for 7 nights, 1 cottage
NZ$523 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Property grounds
Outdoor dining
Living area
Terrace/patio
Exceptional
(11 reviews)

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

Huntingtown

8% off
NZ$6,513
for 7 nights, 1 cottage
NZ$930 per night
includes taxes & fees
Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
Directly next door to Sunrise Garden park
Beautiful North Beach, MD
Beautiful North Bach, MD
Open-concept living area and kitchen
Exceptional
(21 reviews)

Unbelievable beach views for 6

North Beach

8% off
NZ$3,748
for 7 nights, 1 apartment
NZ$535 per night
includes taxes & fees
Unbelievable beach views for 6
Living area
Room
Private kitchen
Living area
Exceptional
(15 reviews)

Clover Cottage - 6BR 4Bath Getaway in Old Town

Alexandria

7% off
NZ$10,726
for 7 nights, 1 cottage
NZ$1,532 per night
includes taxes & fees
Clover Cottage - 6BR 4Bath Getaway in Old Town
Living area
Living area
Interior
Private kitchen
Wonderful
(12 reviews)

Posh House Near DC MGM National Harbor

Alexandria

8% off
NZ$6,243
for 7 nights, 1 home
NZ$892 per night
includes taxes & fees
Posh House Near DC MGM National Harbor
Exterior
Foyer
Bathroom
Room
Exceptional
(27 reviews)

Guest Quarters at the Inn - 102

North Beach

8% off
NZ$2,551
for 7 nights, 1 apartment
NZ$364 per night
includes taxes & fees
Guest Quarters at the Inn - 102
  • 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)
  • Budds Creek Motocross Park (9.3 mi / 15 km)
  • Maryland International Raceway (9.4 mi / 15.1 km)
  • Chesapeake Beach Water Park (16.4 mi / 26.3 km)
  • Relache Spa (24.2 mi / 39 km)
  • Thanksgiving Farm Wines (25.4 mi / 40.9 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:

  • Breezy Point Beach (14 mi / 22.5 km)
  • Cove Point Beach (20.7 mi / 33.3 km)
  • Piscataway Park (20.8 mi / 33.5 km)
  • Colonial Beach (21.9 mi / 35.3 km)
  • Mount Vernon Trail (22.5 mi / 36.2 km)
  • Potomac River Waterfront Park (25.1 mi / 40.4 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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