A marina with numerous sailboats docked at wooden piers.

Eastern Maryland Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Eastern Maryland vacation rentals

A room with a large bed, multiple windows, and a ceiling fan.

1. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
$227 nightly
The price is $244
Nov 17 - Nov 18
Total with taxes and fees
Salisbury Riverfront Lofts
A living room with two grey sofas, a coffee table, and a ceiling fan.

2. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
$291 nightly
The price is $323
Oct 18 - Oct 19
Total with taxes and fees
Cambridge Apt in Walkable Neighborhood
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

3. Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Salisbury
9.8 out of 10, Exceptional, (25 reviews)
"Great location with plenty of space to relax."
United States
Doug R.
$175 nightly
The price is $185
Oct 18 - Oct 19
Total with taxes and fees
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A beachside boardwalk with shops, a Ferris wheel, and a tram.

4. On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (43 reviews)
"Had great mini vac . The vrbo was right down town lots great shops and good choices for meals. All ready thinking about going back"
United States
Jeffry C.
$207 nightly
The price is $232
Oct 18 - Oct 19
Total with taxes and fees
On Main Street - Apartment C - Berlin, MD
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Oct 19 - Oct 20
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A riverside dock with boats, a covered seating area, and a bridge in the background.

6. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (30 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
$263 nightly
The price is $279
Oct 19 - Oct 20
Total with taxes and fees
Historic Chesapeake City Stay
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

7. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$259 nightly
The price is $286
Oct 18 - Oct 19
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

8. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"
United States
Harold B.
$243 nightly
The price is $257
Oct 19 - Oct 20
Total with taxes and fees
Deal Island Bay Cottage
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

9. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
$355 nightly
The price is $376
Nov 17 - Nov 18
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A modern kitchen with white cabinets, a central island, and a dining area with a wooden table and chairs.

10. Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!

Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!
Midtown Ocean City
9.8 out of 10, Exceptional, (275 reviews)
"Great spot, clean and affordable!"
United States
Beth H.
$181 nightly
The price is $203
Nov 1 - Nov 2
Total with taxes and fees
Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!
A single-story house with a front porch, a door, and a mailbox.

11. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (24 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
$331 nightly
The price is $351
Oct 18 - Oct 19
Total with taxes and fees
Salisbury Hideaway
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

12. 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, (29 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
$118 nightly
The price is $125
Oct 19 - Oct 20
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
A gym with treadmills, dumbbells, and exercise balls, large windows with a view of the ocean.

13. Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,330 reviews)
"Our room.seemed to be all new and we loved how there was a separate living room and bedroom with privacy doors. We had a beautiful view of the bay too from the second floor and we loved being on the sunset side of OC:)"
United States
cara
$104 nightly
The price is $116
Oct 30 - Oct 31
Total with taxes and fees
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

14. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
$240 nightly
The price is $254
Oct 19 - Oct 20
Total with taxes and fees
Sailwinds Loft at Cambridge Creek
A wooden pier extending into calm waters at dusk.

15. Nothing Beats Oceanfront OCMD!!

Nothing Beats Oceanfront OCMD!!
North Ocean City
9.8 out of 10, Exceptional, (27 reviews)
"Very nice stay and the history was very accommodating."
United States
Karen C.
$176 nightly
The price is $198
Oct 18 - Oct 19
Total with taxes and fees
Nothing Beats Oceanfront OCMD!!
A balcony with a view of the beach, two chairs, and a table.

16. Direct Oceanfront condo- AMAZING VIEWS & GREAT AMENITIES!

Direct Oceanfront condo- AMAZING VIEWS & GREAT AMENITIES!
North Ocean City
9.0 out of 10, Wonderful, (52 reviews)
"Great vacation and great place to stay, will hopefully book again next year"
United States
Craig L.
$383 nightly
The price is $429
Oct 18 - Oct 19
Total with taxes and fees
Direct Oceanfront condo- AMAZING VIEWS & GREAT AMENITIES!
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

17. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
$331 nightly
The price is $351
Nov 3 - Nov 4
Total with taxes and fees
Salisbury Cottage
A covered patio with a table and chairs, a white fence, and a view of the greenery.

18. Getaway on 1/2 Acre w/ Deck in Georgetown

Getaway on 1/2 Acre w/ Deck in Georgetown
3.0 star property
Georgetown
10.0 out of 10, Exceptional, (1 review)
"This place is just as you see in the photos; clean, welcoming, great location, and very peaceful. We are certainly looking forward to staying here next year, if available. The contact person was available and answered quickly when I contacted him. "
United States
ANA
$334 nightly
The price is $334
Nov 9 - Nov 10
Total with taxes and fees
Getaway on 1/2 Acre w/ Deck in Georgetown
A wooden cabin with a porch, surrounded by dense forest.

19. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (50 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
$105 nightly
The price is $111
Oct 26 - Oct 27
Total with taxes and fees
Country Get Away Studio Apartment
A room with teal walls, a gray sofa, a white dresser, and a ceiling fan.

20. Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N

Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
North Ocean City
9.2 out of 10, Wonderful, (54 reviews)
"check in/check out were super simple. place was clean, but a little tight for 5. location is great."
United States
Theodore B.
$186 nightly
The price is $208
Oct 19 - Oct 20
Total with taxes and fees
Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
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
"Yay"
Ceara 2-night trip
Posted 2 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.

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