Book Holiday Homes in Eastern Maryland

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Featured Holiday Homes in Eastern Maryland

River Front, Private Single Family Home

River Front, Private Single Family Home

Grasonville
When you stay at this vacation home in Grasonville, you'll be within a 10-minute drive of Chesapeake Exploration Center and Queenstown Premium Outlets.
River Front, Private Single Family Home
Beach Paradise 3-OCEANVIEW DOWNTOWN Luxury Townhome w/garage, steps to BOARDWALK

Beach Paradise 3-OCEANVIEW DOWNTOWN Luxury Townhome w/garage, steps to BOARDWALK

Ocean City
The price is AU$499 per night from 7 Oct to 8 Oct
AU$499
per night
7 Oct - 8 Oct
A stay at this vacation home places you in the heart of Ocean City, steps from Ocean City Beach and Ocean City Boardwalk.
Beach Paradise 3-OCEANVIEW DOWNTOWN Luxury Townhome w/garage, steps to BOARDWALK
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 15-minute walk of Waterman’s Museum and Rock Hall Harbor.
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
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BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
The price is AU$399 per night from 30 Sep to 1 Oct
AU$399
per night
30 Sep - 1 Oct
Located in Rock Hall, this vacation home is within a 15-minute walk of Ferry Park and Waterman’s Museum.
BAYSIDE BUNGALOW
Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties

Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties

Ocean City
With a stay at this vacation home in Ocean City (North Ocean City), you'll be steps from Ocean City Beach and 13 minutes by foot from Maryland Beach.
Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties
BRAND NEW FAMILY FRIENDLY NORTH OC OCEANBLOCK TOWNHOUSE! OCEAN VIEWS!

BRAND NEW FAMILY FRIENDLY NORTH OC OCEANBLOCK TOWNHOUSE! OCEAN VIEWS!

3 out of 5
Ocean City
The price is AU$1,437 per night from 6 Oct to 7 Oct
AU$1,437
per night
6 Oct - 7 Oct
With a stay at this vacation home in Ocean City (North Ocean City), you'll be steps from Ocean City Beach and Maryland Beach.
BRAND NEW FAMILY FRIENDLY NORTH OC OCEANBLOCK TOWNHOUSE! OCEAN VIEWS!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of St. Michaels Museum and Chesapeake Bay Maritime Museum.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!

Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!

Havre De Grace
A stay at this vacation home places you in the heart of Havre De Grace, within a 15-minute walk of Susquehanna Museum at the Lock House and Susquehanna ...
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Beautiful home with ocean view, firepit, central AC, & washer/dryer

Beautiful home with ocean view, firepit, central AC, & 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 ...
Beautiful home with ocean view, firepit, central AC, & washer/dryer
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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
429 Holiday Homes
Lowest Price
AU$127
Highest Price
AU$1,437
Popular accommodation
River Front, Private Single Family Home, Beach Paradise 3-OCEANVIEW DOWNTOWN Luxury Townhome w/garage, steps to BOARDWALK, Waterfront w/private pier, pool, Hot Tub, kayaks and in town., BAYSIDE BUNGALOW, Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties, BRAND NEW FAMILY FRIENDLY NORTH OC OCEANBLOCK TOWNHOUSE! OCEAN VIEWS!, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!, Beautiful home with ocean view, firepit, central AC, & washer/dryer

Top trending hotels in Eastern Maryland

Fenwick Inn

Fenwick Inn

2 out of 5
13801 Coastal Highway, Ocean City, MD
Fully refundableReserve now, pay when you stay
The price is AU$127 per night from 30 Sep to 1 Oct
AU$127
per night
30 Sep - 1 Oct
With a stay at Fenwick Inn in Ocean City (North Ocean City), you'll be a 5-minute walk from Ocean City Beach and 5 minutes by foot from Maryland Beach.
Fenwick Inn
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street, Ocean City, MD
The price is AU$193 per night from 30 Sep to 1 Oct
AU$193
per night
30 Sep - 1 Oct
With a stay at Princess Royale Oceanfront Resort in Ocean City (North Ocean City), you'll be a 3-minute walk from Ocean City Beach and within a 5-minute drive ...
Princess Royale Oceanfront Resort
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$188 per night from 2 Oct to 3 Oct
AU$188
per night
2 Oct - 3 Oct
With a stay at Grand Hotel Ocean City Oceanfront in Ocean City (Downtown Ocean City), you'll be steps from Ocean City Beach and Ocean City Boardwalk.
Grand Hotel Ocean City Oceanfront
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Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

3 out of 5
11700 Coastal Hwy, Ocean City, MD
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 30 Sep to 1 Oct
AU$143
per night
30 Sep - 1 Oct
With a stay at Carousel Resort Hotel & Condominiums, you'll be centrally located in Ocean City, steps from Ocean City Beach and 9 minutes by foot from Maryland ...
Carousel Resort Hotel & Condominiums
Don't see what you're looking for?
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.