Eastern Maryland Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Eastern Maryland vacation rentals

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, (38 reviews)
"Very cool place. "
United States
Eric L.
$196 nightly
The price is $207
Mar 8 - Mar 9
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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, (32 reviews)
"Great location, place very clean and perfect for our trip!"
United States
Ed S.
$296 nightly
The price is $329
Mar 6 - Mar 7
Total with taxes and fees
Charming 2-Bed Condo Steps From the Beach!
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (24 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
$240 nightly
The price is $254
Mar 6 - Mar 7
Total with taxes and fees
Sailwinds Loft at Cambridge Creek
Exterior

Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Coconut Malorie Resort Ocean City, Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,301 reviews)
"Everything was great :) Great location...great staff!"
United States
Daria
$92 nightly
The price is $103
Mar 15 - Mar 16
Total with taxes and fees
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
Property grounds

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (12 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
$575 nightly
The price is $610
Mar 9 - Mar 10
Total with taxes and fees
Turnbridge Manor
Smart TV

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
8.8 out of 10, Excellent, (10 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
$583 nightly
The price is $618
Mar 6 - Mar 7
Total with taxes and fees
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Everything was clean and neat and welcoming "
United States
Iriana J.
$144 nightly
The price is $159
Mar 9 - Mar 10
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$239 nightly
The price is $253
Mar 10 - Mar 11
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
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, (8 reviews)
"Clean and comfortable. Very nice stay in the country!"
United States
Daniel B.
$152 nightly
The price is $161
Mar 6 - Mar 7
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Dining

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
$397 nightly
The price is $421
Mar 6 - Mar 7
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Smart TV

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
$501 nightly
The price is $531
Mar 8 - Mar 9
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV, foosball, books

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Chesapeake City
9.4 out of 10, Exceptional, (3 reviews)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
$291 nightly
The price is $308
Mar 8 - Mar 9
Total with taxes and fees
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
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
$242 nightly
The price is $261
Mar 16 - Mar 17
Total with taxes and fees
Salisbury Riverfront Lofts
City view

Americana Condos 10th street

Americana Condos 10th street
3.5 star property
Downtown Ocean City
8.4 out of 10, Very Good, (19 reviews)
"straight fire, definitely going back"
United States
stephen
$436 nightly
The price is $488
Mar 12 - Mar 13
Total with taxes and fees
Americana Condos 10th street
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
Mar 8 - Mar 9
Total with taxes and fees
Historic Chesapeake City Stay
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (53 reviews)
"Great place, will stay again"
United States
Matt S.
$255 nightly
The price is $270
Mar 6 - Mar 7
Total with taxes and fees
Waterfront Getaway with Dock
Living area

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, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
$196 nightly
The price is $208
Mar 10 - Mar 11
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
$246 nightly
The price is $260
Mar 6 - Mar 7
Total with taxes and fees
Deal Island Bay Cottage
Sun loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (148 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
$494 nightly
The price is $524
Mar 9 - Mar 10
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
TV, fireplace

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
$458 nightly
The price is $480
Mar 8 - Mar 9
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
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

The Americana Hotel

The Americana Hotel

10/10 Excellent
"Love the ocean front rooms nice size balcony, best if you can get a end room, more windows"
Dipesh 1-night trip
Posted 11 hours ago
The Americana Hotel

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 $103 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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