Search Vacation Homes in Eastern Maryland

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Homes in Eastern Maryland

Our top choices for Eastern Maryland vacation homes

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (25)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest

Beach Paradise IX - Luxury 4-Bedrooms BOARDWALK Townhouse with Garage!

9.8 out of 10, Exceptional, (20)
"Would stay again "
Beach Paradise IX - Luxury 4-Bedrooms BOARDWALK Townhouse with Garage!

SOUTH BEACH 601 ULTRA LUXURIOUS BOARDWALK GYM IN/OUT POOL

8.8 out of 10, Excellent, (28)
"Property was beautiful, kitchen should be restocked, 2 of the beds need new mattresses, more lighting for reading in the living area, easier access to building, luggage carts for easier transport from car to room! We are very happy with the rental over all"
SOUTH BEACH 601 ULTRA LUXURIOUS BOARDWALK GYM IN/OUT POOL

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

10.0 out of 10, Exceptional, (94)
"The property was great. Large kitchen, comfortable beds, and an amazing outdoor area. Laurie was friendly, responsive, and very accommodating. "
The price is SAR 750
SAR 1,403 total
includes taxes & fees
24 Oct - 25 Oct
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

Wave Watcher's Condo - Steps to the beach!

9.8 out of 10, Exceptional, (9)
"The place was very clean and very cool, which was nice on the hot days. Some of my party slept on the floor so I'd say it sleeps 10 but overall, wonderful place would recommend to anyone!"
Wave Watcher's Condo - Steps to the beach!

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (48)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is SAR 750
SAR 1,101 total
includes taxes & fees
6 Oct - 7 Oct
BAYSIDE BUNGALOW

Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool

9.0 out of 10, Wonderful, (93)
"The house is big and beautiful and was very clean and comfortable. "
Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

9.8 out of 10, Exceptional, (7)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

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

9.6 out of 10, Exceptional, (62)
"Cozy place that was fine for the 2 of us and 2 dogs.Fenced yard was great.Fun downtown that we walked many times.Jamies Donut shop is a must stop."
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (15)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is SAR 600
SAR 1,332 total
includes taxes & fees
30 Sep - 1 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

DownByTheBay_107- Spacious Beach Home 4BR/3.5BA @Broad Marsh/Pool/Steps to Beach

9.6 out of 10, Exceptional, (37)
"The property was easy to find, exceptionally clean, and very enjoyable! Would definitely book again!"
DownByTheBay_107- Spacious Beach Home 4BR/3.5BA @Broad Marsh/Pool/Steps to Beach

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (53)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay

⭐️Gorgeous Sunset Island Private Beach In/Outdoor Pools⭐️

9.4 out of 10, Exceptional, (14)
"My family loves Sunset Island. We thoroughly enjoyed staying at this condo. "
⭐️Gorgeous Sunset Island Private Beach In/Outdoor Pools⭐️

5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+

5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+

Gorgeous Beach Home in Bayside Resort! 3 Master suites!

10.0 out of 10, Exceptional, (128)
"Home was very nice and well kept. Close to beaches with very nice amenities on site. We had a couple of issues that were immediately addressed by the landlord. I would definitely recommend this property. "
Gorgeous Beach Home in Bayside Resort! 3 Master suites!

Cottage near the Bay

8.8 out of 10, Excellent, (46)
"great, peaceful "
The price is SAR 304
SAR 700 total
includes taxes & fees
1 Oct - 2 Oct
Cottage near the Bay

Spacious Home w Parking Steps to Beach Boardwalk Concerts Festivals.

9.6 out of 10, Exceptional, (17)
"Highly recommended, thoughtful and caring hosts. Every amenity was available."
Spacious Home w Parking Steps to Beach Boardwalk Concerts Festivals.

Bring your boat! Townhome on Bayside 94th St w/a unique Kids/Teen Bedroom

3.5 star property
10.0 out of 10, Exceptional, (16)
"Super place, very convenient to everything, lots of space! We’d absolutely stay here again!"
Bring your boat! Townhome on Bayside 94th St w/a unique Kids/Teen Bedroom

Waterfront Getaway-walk to beach and local favorites!

10.0 out of 10, Exceptional, (37)
"Home was exactly as advertised, well equipped, charming decor, water views, and convenient location!"
Waterfront Getaway-walk to beach and local favorites!

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (54)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Eastern Maryland Hotel Reviews