A marina with numerous sailboats docked at wooden piers.

Holiday Rentals in Eastern Maryland

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Eastern Maryland holiday 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, (28 reviews)
"I loved the location, the cleanliness and how good I felt being there. Thank you"
United States
Carmen
The price is €225
includes taxes & fees
8 Nov - 9 Nov
Salisbury Riverfront Lofts
A row of mobile homes with a one-way sign, a covered porch, and a street sign indicating 'Shore Point Lane'.

2. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (403 reviews)
"Everything was clean and comfortable. Would stay here again."
United States
Kelly
The price is €113
includes taxes & fees
29 Nov - 30 Nov
Shore Point Cottages
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.
The price is €162
includes taxes & fees
4 Dec - 5 Dec
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.

4. 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
The price is €288
includes taxes & fees
5 Nov - 6 Nov
Cambridge Apt in Walkable Neighborhood
A balcony with a view of a river, greenery, and distant buildings.

5. 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, (1,331 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
The price is €100
includes taxes & fees
28 Nov - 29 Nov
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A single-story house with a front porch, a door, and a mailbox.

6. 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.
The price is €276
includes taxes & fees
5 Nov - 6 Nov
Salisbury Hideaway
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

7. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is €223
includes taxes & fees
5 Nov - 6 Nov
Deal Island Bay Cottage
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

8. 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.
The price is €291
includes taxes & fees
9 Nov - 10 Nov
Salisbury Cottage
A deck with a view of a marina, including boats and docks.

9. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is €234
includes taxes & fees
12 Nov - 13 Nov
Cass-N-Reel Luxury Houseboat
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

10. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is €137
includes taxes & fees
5 Nov - 6 Nov
First Floor Studio Apartment in Historic Chestertown
A living room with a sofa, a coffee table, a chair, and a dining table. There are two windows with curtains, a lamp, and a painting on the wall.

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.2 out of 10, Wonderful, (44 reviews)
"Great location and very cozy. I wish we could’ve stayed longer."
United States
Christopher W.
The price is €205
includes taxes & fees
5 Nov - 6 Nov
On Main Street - Apartment C - Berlin, MD
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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is €107
includes taxes & fees
5 Nov - 6 Nov
Guest Suite for up to 2 in a Victorian on the Chester River
A brick building with a white porch and a well-maintained lawn.

13. 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.
The price is €323
includes taxes & fees
17 Nov - 18 Nov
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A rustic cabin with a sign reading 'A-M-A-L-G-A-M-A-T-E-D' and a small outdoor seating area with two chairs.

14. Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!

Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!
Seaford
10.0 out of 10, Exceptional, (1 review)
"This was a clean, comfortable place to stay. We only stayed one night, but would've enjoyed staying longer. Sitting outside with coffee in the morning was special. The number of different birds we heard was amazing. We didn't have time to explore the pond, but it added to a nice, quiet stay."
United States
Whitney H.
The price is €141
includes taxes & fees
3 Dec - 4 Dec
Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!
A living room with a sofa, a coffee table, and a patterned rug. There is a window with curtains, a door, and a small table with chairs.

15. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
The price is €269
includes taxes & fees
5 Nov - 6 Nov
Historic Chesapeake City Stay
A living room with hardwood flooring, a blue sofa, a small table with a lamp, and a large window with a view.

16. Pet-Friendly Cottage on 1.5 Acres Near Beaches!

Pet-Friendly Cottage on 1.5 Acres Near Beaches!
Selbyville
The price is €187
includes taxes & fees
8 Nov - 9 Nov
Pet-Friendly Cottage on 1.5 Acres Near Beaches!
A covered patio with a table and chairs, a white fence, and a view of the greenery.

17. 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
The price is €298
includes taxes & fees
9 Nov - 10 Nov
Getaway on 1/2 Acre w/ Deck in Georgetown
A house with a blue front door, two windows, and a small porch.

18. 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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is €248
includes taxes & fees
12 Nov - 13 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

19. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (65 reviews)
"Nice cottage at the end of a quiet lane, priced reasonably. Host is very accommodating. We had a lovely stay and enjoyed our time in Crisfield."
United States
Karen J.
The price is €161
includes taxes & fees
5 Nov - 6 Nov
Cottage near the Bay
A well-lit living room with a sofa, armchair, dining table, and a television.

20. Direct OceanFront Condo on the center of the Boardwalk Newly Remodeled with Pool

Direct OceanFront Condo on the center of the Boardwalk Newly Remodeled with Pool
Downtown Ocean City
9.6 out of 10, Exceptional, (87 reviews)
"Cozy. Great location!"
United States
Renee H.
Direct OceanFront Condo on the center of the Boardwalk Newly Remodeled with Pool
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

10/10 Excellent
"My great niece and I had an overnight girls trip, we had a great time. Loved our room and frint desk person was so friendly"
Angela 1-night trip
Posted less than an hour ago
Princess Royale Oceanfront Resort

Find out more about Eastern Maryland

Everything you need to know about Eastern Maryland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Eastern Maryland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Eastern Maryland holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Eastern Maryland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Eastern Maryland holiday rentals we have selected for you start as low as €100 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Eastern Maryland rentals

At Expedia, we put the best Eastern Maryland holiday 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 holiday.

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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