Eastern Maryland Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Eastern Maryland vacation rentals

House (3 Bedrooms) | Front of property

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
$242 nightly
The price is $271
May 6 - May 7
Total with taxes and fees
6 Mi to Salisbury: Forest-view Sanctuary!
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
$263 nightly
The price is $279
May 6 - May 7
Total with taxes and fees
Historic Chesapeake City Stay
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
$144 nightly
The price is $159
May 7 - May 8
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Apartment D: Riverfront Grand | 2 bedrooms, individually decorated, individually furnished

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (23 reviews)
"It was a great stay nice comfortable place "
United States
Adam
$238 nightly
The price is $256
May 6 - May 7
Total with taxes and fees
Salisbury Riverfront Lofts
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (21 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
$118 nightly
The price is $125
May 6 - May 7
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"This place is out in the country, but a short distance to lots of places we wanted to see, shop at, visit."
United States
Richard
$105 nightly
The price is $111
May 12 - May 13
Total with taxes and fees
Country Get Away Studio Apartment
Beach nearby

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.2 out of 10, Wonderful, (30 reviews)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
$226 nightly
The price is $253
May 12 - May 13
Total with taxes and fees
On Main Street - Apartment C - Berlin, MD
Interior

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (54 reviews)
"Great little place "
United States
Eric R.
$176 nightly
The price is $187
May 8 - May 9
Total with taxes and fees
Cottage near the Bay
Fridge, microwave, oven, stovetop

Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Nice large, bright kitchen, each room has a bathroom! Nice river view, many shops within walking distance and good coffee and breakfast right diwnstairs! Loved the funky, whimsical decor too."
United States
Joan
$175 nightly
The price is $185
May 6 - May 7
Total with taxes and fees
Retro Hipster: Close to downtown, dining and fun
Terrace/patio

Restful Non-Shared Basement Suite In Harford MD

Restful Non-Shared Basement Suite In Harford MD
Bel Air
10.0 out of 10, Exceptional, (2 reviews)
"Check in was quick and easy, property was exactly as I thought it would be and amenities were great."
United States
Joseph N.
$100 nightly
The price is $105
May 18 - May 19
Total with taxes and fees
Restful Non-Shared Basement Suite In Harford MD
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (20 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$260 nightly
The price is $287
May 6 - May 7
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
9.8 out of 10, Exceptional, (10 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
May 6 - May 7
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Outdoor pool

Comfortable cottage in gated community, 5 mins to OC and Assateague

Comfortable cottage in gated community, 5 mins to OC and Assateague
Assateague Pointe
9.8 out of 10, Exceptional, (45 reviews)
"great place, great location, safe secure and everything we needed to get to assateague where the rest of the family were camping"
United States
Thomas B.
$324 nightly
The price is $363
May 7 - May 8
Total with taxes and fees
Comfortable cottage in gated community, 5 mins to OC and Assateague
Exterior

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (42 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
$197 nightly
The price is $208
May 6 - May 7
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Smart TV, books, offices

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (37 reviews)
"My family and I had a great stay was a comfy and safe space to relax and enjoy our Halloween weekend would definitely recommend!"
United States
Mackenzie N.
$323 nightly
The price is $342
May 6 - May 7
Total with taxes and fees
Salisbury Cottage
Outdoor dining

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

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Berlin
9.8 out of 10, Exceptional, (100 reviews)
"Property was perfect for us and our dogs."
United States
Jeffrey B.
$257 nightly
The price is $288
May 10 - May 11
Total with taxes and fees
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
TV, fireplace

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
$414 nightly
The price is $433
May 6 - May 7
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
Fridge, microwave, oven, stovetop

Charming 2-Bed Condo Steps From the Beach!

Charming 2-Bed Condo Steps From the Beach!
North Ocean City
10.0 out of 10, Exceptional, (33 reviews)
"Great location, place very clean and perfect for our trip!"
United States
Ed S.
$294 nightly
The price is $327
May 6 - May 7
Total with taxes and fees
Charming 2-Bed Condo Steps From the Beach!
Smart TV

Beach Days & Bay Sunsets. Your Easy OCMD Escape!

Beach Days & Bay Sunsets. Your Easy OCMD Escape!
North Ocean City
9.0 out of 10, Wonderful, (37 reviews)
"We really enjoyed our stay here! Close to the beach and in walking distance of a lot of activities but also very quiet! Loved it!"
United States
Renee P.
$184 nightly
The price is $206
May 6 - May 7
Total with taxes and fees
Beach Days & Bay Sunsets. Your Easy OCMD Escape!
Smart TV

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (6 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
$206 nightly
The price is $219
May 11 - May 12
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
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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Top Eastern Maryland Hotel Reviews

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

8/10 Good
"Clean and friendly staff"
KELVIN 2-night trip
Posted 3 hours ago
Princess Royale Oceanfront Resort

Find out more about Eastern Maryland

Everything you need to know about Eastern Maryland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Eastern Maryland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Eastern Maryland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Eastern Maryland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Eastern Maryland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Eastern Maryland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $124 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Eastern Maryland rentals

At Expedia, we put the best Eastern Maryland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Eastern Maryland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Eastern Maryland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Eastern Maryland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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