Eastern Shore Vacation Rentals

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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Eastern Shore

Exterior
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Aparthotel in Midtown Ocean City

3.0 star property
7.4 out of 10, Good, (1297)
"Scenic area with wonderful wooden bridges and view of water. There was no hot water to shower, but not a deal breaker."
United States
Isolda
$91 nightly
The price is $101
Dec 16 - Dec 17
Total with taxes and fees
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
Apartment, 2 Bedrooms | Private kitchen | Fridge
Majestic Hotel & Apartments

Aparthotel in Downtown Ocean City

2.5 star property
6.2 out of 10, (349)
"Clean and very friendly staff"
United States
Randy
Majestic Hotel & Apartments
Exterior
Saint Tropez

Apartment in North Ocean City

3.0 star property
9.2 out of 10, Wonderful, (131)
"I always stay here when in OC"
United States
Terry
Saint Tropez
Deluxe Cottage | Private kitchen | Fridge, microwave, stovetop, toaster
Shore Point Cottages

Cottage in Berlin

3.0 star property
9.4 out of 10, Exceptional, (299)
"Was a great place to bring kids and dogs! "
United States
AMANDA
$124 nightly
The price is $138
Nov 30 - Dec 1
Total with taxes and fees
Shore Point Cottages
Property grounds
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

Vacation Home in North Ocean City

9.8 out of 10, Exceptional, (133)
"A very clean property."
United States
David Y.
$279 nightly
The price is $310
Dec 3 - Dec 4
Total with taxes and fees
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
On the beach
Americana Condos 10th street

Condo in Downtown Ocean City

3.5 star property
8.4 out of 10, Very Good, (19)
"straight fire, definitely going back"
United States
stephen
$399 nightly
The price is $443
Nov 28 - Nov 29
Total with taxes and fees
Americana Condos 10th street
Indoor pool, seasonal outdoor pool
Club Ocean Villas II by Coolvacay

Apartment in North Ocean City

3.5 star property
8.6 out of 10, Excellent, (58)
"Property was in a great location. Check in and check out was easy. Having a hot tub and deck with table and chairs was nice. Unit was clean with an exception of the floors. I can understand it being a little sandy because of being at the beach, but there were tortilla chips in several areas of the floor. "
United States
Tami
Club Ocean Villas II by Coolvacay
Exterior
Boardwalk One

Aparthotel in Downtown Ocean City

3.0 star property
7.4 out of 10, Good, (170)
"Close to boardwalk, beach, shopping and dining. Also it was very affordable."
United States
ANGELA
Boardwalk One
Outdoor dining
Updated, Direct Bay Front, Bay Front Pool, 3 Blocks to Beach and Boardwalk

Condo in Downtown Ocean City

10.0 out of 10, Exceptional, (102)
"We had an amazing stay at this property. It was well stocked, clean, had comfy beds, and a beautiful view. "
United States
Abby W.
Updated, Direct Bay Front, Bay Front Pool, 3 Blocks to Beach and Boardwalk
Balcony view
Monte Carlo Condos

Condo in Downtown Ocean City

3.0 star property
6.8 out of 10, (58)
"The condo was small, but it’s still accommodated my family of eight and we were right next to the pool, which was great for the kids anytime we needed something. We just called the Hotel and it was brought over in a reasonable amount of time or we could pick it up later. Staff were very friendly."
United States
Amy
Monte Carlo Condos
TV, fireplace, video games, DVD player
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Condo in Downtown Ocean City

9.8 out of 10, Exceptional, (60)
"Perfect family beach house, we had a blast! Our family of 7 stayed for 3 nights. We loved the easy check-in, location, and spacious, clean condo. Thank you for letting us use your gorgeous home Kim, we really enjoyed our stay!"
United States
Amy R.
$316 nightly
The price is $351
Nov 30 - Dec 1
Total with taxes and fees
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo
Fridge, microwave, oven, stovetop
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

Vacation Home in North Ocean City

9.8 out of 10, Exceptional, (119)
"Great property in a great location. Host was quick to get ahold of and the instructions were incredibly easy. Highly recommend this property for a family or large group. We would stay here again!"
United States
Joseph G.
$270 nightly
The price is $300
Nov 30 - Dec 1
Total with taxes and fees
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
On the beach
ON TOP FLOOR OF MARRIOTT - Luxury Boardwalk/Beach 1400 sq ft + Hotel amenities

Condo in Downtown Ocean City

9.8 out of 10, Exceptional, (268)
"Property was cleaned and the location is exceptional. We had a wonderful stay."
United States
Momolu D.
ON TOP FLOOR OF MARRIOTT - Luxury Boardwalk/Beach 1400 sq ft + Hotel amenities
Premium Condo, Balcony, Bay View | Balcony
Bay Club Resort by Coolvacay

Condo resort in Midtown Ocean City

3.0 star property
8.4 out of 10, Very Good, (39)
"One of the cleanest places I’ve stay at loved it ! "
United States
Kelsey
Bay Club Resort by Coolvacay
Exterior
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Vacation Home in Perryville

10.0 out of 10, Exceptional, (20)
"Great location on the upper Chesapeake! Saw eagles and osprey every day from the property, and heard an eagle for the first time."
United States
JAMES W.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront
Fridge, microwave, oven, stovetop
Ocean City Maryland Condo, ocean side 50 steps to the beach! On 7 40th Street

Condo in Midtown Ocean City

9.8 out of 10, Exceptional, (244)
"Will stay again. Perfect for our needs. "
United States
thomasine m.
$204 nightly
The price is $226
Dec 1 - Dec 2
Total with taxes and fees
Ocean City Maryland Condo, ocean side 50 steps to the beach! On 7 40th Street
Outdoor dining
Downtown St. Michaels | Porch + Pet-Friendly

Apartment in Saint Michaels

Downtown St. Michaels | Porch + Pet-Friendly
Terrace/patio
⭐️Brand New High End Luxury Bayside Mansion Pool⭐️

Vacation Home in North Ocean City

9.8 out of 10, Exceptional, (11)
"Family reunion with our children and grandchildren There were 20 of us staying in this home and it was absolutely perfect. Plenty of room, plenty to do. We just loved it. "
United States
Sue S.
⭐️Brand New High End Luxury Bayside Mansion Pool⭐️
Dining
BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

Vacation Home in North Ocean City

9.6 out of 10, Exceptional, (57)
"The place was beautiful , convenient to walk around to the beach and the stores "
United States
Theresa K.
BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!
Apartment D: Riverfront Grand | In-room dining
Salisbury Riverfront Lofts

Apartment in Salisbury

3.0 star property
9.4 out of 10, Exceptional, (23)
"It was a great stay nice comfortable place "
United States
Adam
$245 nightly
The price is $264
Nov 30 - Dec 1
Total with taxes and fees
Salisbury Riverfront Lofts
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 Shore Hotel Reviews

Red Roof Inn Perryville

Red Roof Inn Perryville

10/10 Excellent
"."
Jared 1-night trip
Posted 1 day ago
Red Roof Inn Perryville

Find out more about Eastern Shore

Everything you need to know about Eastern Shore 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 Shore 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 Shore vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Eastern Shore vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Eastern Shore. 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 Shore 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 Shore rentals

At Expedia, we put the best Eastern Shore 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 Shore 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 Shore 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 Shore. 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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