Book Holiday Homes in Eastern Maryland

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Featured Holiday Homes in Eastern Maryland

DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

Ocean City
With a stay at this vacation home in Ocean City (North Ocean City), you'll be a 3-minute walk from Ocean City Beach and within a 5-minute drive of Maryland ...
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15
Pet-Friendly Home on Chester River w/ Dock!

Pet-Friendly Home on Chester River w/ Dock!

2 out of 5
Chestertown
When you stay at this vacation home in Chestertown, you'll be within a 5-minute drive of Washington College.
Pet-Friendly Home on Chester River w/ Dock!
Four Bedroom Oceanside Townhome with Pool and View

Four Bedroom Oceanside Townhome with Pool and View

Ocean City
Located in Ocean City (Midtown Ocean City), this vacation home is steps from Ocean City Beach and a 3-minute drive from Ocean City Boardwalk.
Four Bedroom Oceanside Townhome with Pool and View
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Lovely beachfront condo with pool/hot tub access, scenic balcony & washer/dryer

Lovely beachfront condo with pool/hot tub access, scenic balcony & washer/dryer

Ocean City
With a stay at this vacation home in Ocean City (North Ocean City), you'll be a 1-minute drive from Ocean City Beach and 9 minutes from Ocean City ...
Lovely beachfront condo with pool/hot tub access, scenic balcony & washer/dryer
Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly

Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly

Ocean City
With a stay at this vacation home in Ocean City (North Ocean City), you'll be within a 15-minute drive of Ocean City Boardwalk and Ocean City Beach.
Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly
Saint Louis Ave townhouse central AC & private washer/dryer - near the ocean

Saint Louis Ave townhouse central AC & private washer/dryer - near the ocean

Ocean City
With a stay at this vacation home, you'll be centrally located in Ocean City, within a 5-minute walk of Ocean City Boardwalk and Ocean City Beach.
Saint Louis Ave townhouse central AC & private washer/dryer - near the ocean
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Dollhouse in Central Historic St Michaels
PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Ocean City
A stay at this vacation home places you in the heart of Ocean City, steps from Ocean City Boardwalk and Ocean City Beach.
PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck
4BR Townhouse with Garage & Pool in Downtown OC- Close to Beach & Boardwalk!

4BR Townhouse with Garage & Pool in Downtown OC- Close to Beach & Boardwalk!

Ocean City
With a stay at this vacation home, you'll be centrally located in Ocean City, within a 5-minute walk of Ocean City Boardwalk and Ocean City Beach.
4BR Townhouse with Garage & Pool in Downtown OC- Close to Beach & Boardwalk!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Eastern Maryland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Eastern Maryland vacation homes are the perfect way for you to wing it.

Holiday houses in Eastern Maryland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Eastern Maryland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Eastern Maryland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Eastern Maryland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Eastern Maryland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Eastern Maryland Holiday Homes essential information

Accommodation
487 Holiday Homes
Lowest Price
AU$131
Highest Price
AU$181
Popular accommodation
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15, Pet-Friendly Home on Chester River w/ Dock!, Four Bedroom Oceanside Townhome with Pool and View, Lovely beachfront condo with pool/hot tub access, scenic balcony & washer/dryer, Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly, Saint Louis Ave townhouse central AC & private washer/dryer - near the ocean, Dollhouse in Central Historic St Michaels, PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck, 4BR Townhouse with Garage & Pool in Downtown OC- Close to Beach & Boardwalk!

Top trending hotels in Eastern Maryland

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
2100 N Baltimore Ave, Ocean City, MD
Fully refundableReserve now, pay when you stay
The price is AU$131 per night from 2 Jan to 3 Jan
AU$131
includes taxes & fees
2 Jan - 3 Jan 2025
With a stay at Grand Hotel Ocean City Oceanfront in Ocean City (Downtown Ocean City), you'll be steps from Ocean City Boardwalk and Ocean City Beach.
Grand Hotel Ocean City Oceanfront
Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront

3 out of 5
1 16th Street, Ocean City, MD
Fully refundableReserve now, pay when you stay
The price is AU$139 per night from 7 Jan to 8 Jan
AU$139
includes taxes & fees
7 Jan - 8 Jan 2025
A stay at Hyatt Place Ocean City / Oceanfront places you in the heart of Ocean City, steps from Ocean City Boardwalk and a 3-minute drive from Trimper's ...
Hyatt Place Ocean City / Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street, Ocean City, MD
The price is AU$138 per night from 5 Jan to 6 Jan
AU$138
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Princess Royale Oceanfront Resort in Ocean City (North Ocean City), you'll be a 1-minute drive from Ocean City Beach and 8 minutes from Ocean ...
Princess Royale Oceanfront Resort
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Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites

4 out of 5
3200 N Baltimore Ave, Ocean City, MD
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 2 Jan to 3 Jan
AU$181
includes taxes & fees
2 Jan - 3 Jan 2025
With a stay at Hilton Ocean City Oceanfront Suites, you'll be centrally located in Ocean City, steps from Ocean City Beach and 11 minutes by foot from Ocean ...
Hilton Ocean City Oceanfront Suites
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See all available properties in Eastern Maryland
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.