A marina with numerous sailboats docked at wooden piers.

Eastern Maryland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 8 - Nov 9
Total with taxes and fees
Salisbury Riverfront Lofts
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

2. 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.
$177 nightly
The price is $187
Oct 11 - Oct 12
Total with taxes and fees
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A living room with two grey sofas, a coffee table, and a ceiling fan.

3. 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 17 - Oct 18
Total with taxes and fees
Cambridge Apt in Walkable Neighborhood
A single-story house with a front porch, a door, and a mailbox.

4. 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.
$335 nightly
The price is $355
Oct 14 - Oct 15
Total with taxes and fees
Salisbury Hideaway
A beachside boardwalk with shops, a Ferris wheel, and a tram.

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (43 reviews)
"A perfect location if you want to explore downtown Berlin. It’s right in the heart of Main Street walking distance to everything.The apartment had everything we needed and was very cozy and clean . Would definitely book this spot again."
United States
Sarah V.
$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.

6. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"
United States
Charr
$144 nightly
The price is $159
Oct 12 - Oct 13
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A gym with treadmills, dumbbells, and exercise balls, large windows with a view of the ocean.

7. 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, (1,326 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
$90 nightly
The price is $101
Oct 11 - Oct 12
Total with taxes and fees
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
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 12 - Oct 13
Total with taxes and fees
Deal Island Bay Cottage
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

9. 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.
$363 nightly
The price is $385
Nov 8 - Nov 9
Total with taxes and fees
Salisbury Cottage
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

10. 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 12 - Oct 13
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
A riverside dock with boats, a covered seating area, and a bridge in the background.

11. 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 15 - Oct 16
Total with taxes and fees
Historic Chesapeake City Stay
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

12. 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 11 - Oct 12
Total with taxes and fees
Sailwinds Loft at Cambridge Creek
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

13. 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.
$266 nightly
The price is $294
Oct 12 - Oct 13
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A covered porch with wooden flooring, white railings, and two green chairs.

14. Wilmington Terrace

Wilmington Terrace
3.0 star property
Downtown Ocean City
8.2 out of 10, Very good, (12 reviews)
"The staff was very friendly, the apartment was very clean, I love that pets are welcome and the beach and boardwalk are less than 2 minutes walk. EXCELLENT!"
United States
Jennifer
$188 nightly
The price is $211
Oct 11 - Oct 12
Total with taxes and fees
Wilmington Terrace
A modern kitchen with white cabinets, a central island, and a dining area with a wooden table and chairs.

15. 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, (274 reviews)
"Great spot, clean and affordable!"
United States
Beth H.
$180 nightly
The price is $201
Nov 1 - Nov 2
Total with taxes and fees
Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

16. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (14 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
$361 nightly
The price is $383
Oct 27 - Oct 28
Total with taxes and fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A large outdoor swimming pool with people swimming and lounging, surrounded by a fence and shaded areas.

17. 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, (57 reviews)
"The cottage location is great for golf, less than 20 minutes ride to most courses. Also dining in Berlin is better than traffic to Oean City."
United States
Joe
$326 nightly
The price is $365
Oct 11 - Oct 12
Total with taxes and fees
Comfortable cottage in gated community, 5 mins to OC and Assateague
A covered patio with a table and chairs, overlooking a beach.

18. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (530 reviews)
"Very bice"
United States
Robert
$83 nightly
The price is $93
Oct 11 - Oct 12
Total with taxes and fees
Majestic Hotel & Apartments
A balcony with two chairs and a table, overlooking a beach with the ocean and a clear sky.

19. #1 Rated Condo, Oceanfront, with Bay View Too

#1 Rated Condo, Oceanfront, with Bay View Too
North Ocean City
10.0 out of 10, Exceptional, (342 reviews)
"Had a great stay "
United States
Ed B.
$249 nightly
The price is $279
Oct 19 - Oct 20
Total with taxes and fees
#1 Rated Condo, Oceanfront, with Bay View Too
A covered patio with a table and chairs, a sliding glass door, and a white fence.

20. Monte Carlo Condos

Monte Carlo Condos
3.0 star property
Downtown Ocean City
7.0 out of 10, Good, (74 reviews)
"Unexpected pet fee on top of resort fees we did expect. Nice and close to boardwalk. Room was quiet, private, spacious."
United States
Ben
$198 nightly
The price is $221
Oct 19 - Oct 20
Total with taxes and fees
Monte Carlo Condos
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 Shore House

The Shore House

8/10 Good
"Good location"
Hugh 1-night trip
Posted 1 day ago
The Shore House

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 $101 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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