Eastern Shore Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Holiday Rentals in Eastern Shore

Apartment, 2 Bedrooms | Private kitchen
Majestic Hotel & Apartments
Majestic Hotel & Apartments
2.5 star property
6.2 out of 10, (340)
"Amazing ocean front and boardwalk access. "
United States
Jeremy
Majestic Hotel & Apartments
Exterior
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
3.0 star property
7.4 out of 10, Good, (1292)
"We had a really lovely time and the staff was incredibly helpful with all our needs to the music festival we were in town for."
United States
Dana
The price is AU$160
includes taxes & fees
20 Nov - 21 Nov
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
Fridge, microwave, dining tables
Ocean Terrace Family Apartments
Ocean Terrace Family Apartments
3.0 star property
8.0 out of 10, Very good, (31)
"Check in was easy, parking was available and the staff were very helpful!"
United States
Nicole
The price is AU$137
includes taxes & fees
22 Oct - 23 Oct
Ocean Terrace Family Apartments
Exterior
Saint Tropez
Saint Tropez
3.0 star property
9.2 out of 10, Wonderful, (124)
"I always stay here when in OC"
United States
Terry
Saint Tropez
Deluxe Cottage | Private kitchen
Shore Point Cottages
Shore Point Cottages
3.0 star property
9.4 out of 10, Exceptional, (297)
"Was a great place to bring kids and dogs! "
United States
AMANDA
Shore Point Cottages
Exterior
Boardwalk One
Boardwalk One
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
The price is AU$158
includes taxes & fees
22 Oct - 23 Oct
Boardwalk One
Balcony view
Monte Carlo Condos
Monte Carlo Condos
3.0 star property
6.8 out of 10, (57)
"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
The price is AU$343
includes taxes & fees
23 Oct - 24 Oct
Monte Carlo Condos
Standard Apartment | Private kitchen
OCHG Sand Dollars
OCHG Sand Dollars
3.0 star property
6.0 out of 10, (2)
"The property is only 2 houses away from the OC Beach and Boardwalk. "
United States
Kara
OCHG Sand Dollars
Dock
Club Ocean Villas II
Club Ocean Villas II
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
Outdoor dining
Chesapeake Bay House with Dock & Private Beach
Chesapeake Bay House with Dock & Private Beach
10.0 out of 10, Exceptional, (174)
"Nice property. Large enough for 13. Plenty of space to spread out "
United States
Mike J.
Chesapeake Bay House with Dock & Private Beach
Property grounds
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
9.8 out of 10, Exceptional, (132)
"Perfect space and location. Large unit with plenty of space. Easy 5 minute walk to the beach. Many stores nearby (grocery, ice cream, coffee and miniature golf). "
United States
Chris A.
The price is AU$481
includes taxes & fees
2 Nov - 3 Nov
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
Outdoor dining
DownByTheBay_4005 Spacious Direct Oceanfront 4BR 3.5BA Sleep16+ Game Room🏖️
DownByTheBay_4005 Spacious Direct Oceanfront 4BR 3.5BA Sleep16+ Game Room🏖️
9.8 out of 10, Exceptional, (10)
"We really enjoyed how close it was to the convention center, but also how wonderful the beach access was! Best of both worlds. Kinda like a mullet, business up front but party in the back! lol and by party we mean watching the waves and kicking back. "
United States
Deidrah R.
DownByTheBay_4005 Spacious Direct Oceanfront 4BR 3.5BA Sleep16+ Game Room🏖️
Outdoor pool
High Point North Studio M8
High Point North Studio M8
9.6 out of 10, Exceptional, (11)
"A gem located right on the beach! Cute beach themed efficiency. Private walkway to the public beach, which is less than 5 minutes. No private balcony, but there’s a huge window that overlooks the communal balcony and pool. At night if you leave it open you can hear the waves hitting the beach! Host is responsive and location is walking distance to all the stores and food options you need. Highly recommend Robbin’s place!"
United States
Serena P.
High Point North Studio M8
On the beach
Americana Condos 10th street
Americana Condos 10th street
3.5 star property
8.4 out of 10, Very good, (19)
"straight fire, definitely going back"
United States
stephen
The price is AU$813
includes taxes & fees
22 Oct - 23 Oct
Americana Condos 10th street
Fridge, microwave, oven, stovetop
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15
9.8 out of 10, Exceptional, (140)
"Very good time! Property was accurate to listing. "
United States
Shae l.
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15
On the beach
ON TOP FLOOR OF MARRIOTT - Luxury Boardwalk/Beach 1400 sq ft + Hotel amenities
ON TOP FLOOR OF MARRIOTT - Luxury Boardwalk/Beach 1400 sq ft + Hotel amenities
9.8 out of 10, Exceptional, (266)
"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
Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD
Station House East: Upscale Loft in the Historic District Cambridge, MD
10.0 out of 10, Exceptional, (1)
"Location very convenient, flat beautiful, clean, very friendly, respo sive and accommodating hostess! Thank you!"
United States
Solveig S.
The price is AU$394
includes taxes & fees
22 Oct - 23 Oct
Station House East: Upscale Loft in the Historic District Cambridge, MD
Deluxe Apartment, 2 Bedrooms, Kitchen, City View (Shared Balcony, A02) | Living room
The Mallard Apartments
The Mallard Apartments
2.5 star property
6.0 out of 10, (40)
"I have stayed here for several years now. The property is located in a great spot. The rooms are clean but could use updating. All and all it is well worth the money"
United States
Jeffrey
The price is AU$875
includes taxes & fees
24 Oct - 25 Oct
The Mallard Apartments
Exterior
Oceanfront 3 Bedroom Condo directly on the Boardwalk with a Great Balcony
Oceanfront 3 Bedroom Condo directly on the Boardwalk with a Great Balcony
10.0 out of 10, Exceptional, (96)
"View is wonderful from balcony, plenty of room for everyone."
United States
Douglas R.
Oceanfront 3 Bedroom Condo directly on the Boardwalk with a Great Balcony
Terrace/patio
Waterfront house with amazing views. Top of the Chesapeake
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (101)
"The river house has an absolutely amazing view! My kids were thrilled with the chance to fish off a very long dock and even get their feet in the water on a small beach below the house (when the tide was out). Overall, the house was perfect and just big enough for our large family of seven. Matt was very responsive to a few questions I had and was a wonderful host! "
United States
Skye M.
Waterfront house with amazing views. Top of the Chesapeake
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Eastern Shore Hotel Reviews

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"The first floor room is a little difficult to get to. But is well worth the journey. It was awesome to walk right off the patio onto the beach ."
Gregory 2-night trip
Posted 2 days ago
Princess Royale Oceanfront Resort

Find out more about Eastern Shore

Everything you need to know about Eastern Shore 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 Shore holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Shore holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

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

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Eastern Shore 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 Shore holiday rentals we have selected for you start as low as AU$137 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Eastern Shore rentals

At Expedia, we put the best Eastern Shore 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 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 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 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. 

Explore a world of travel with Expedia