Eastern Shore Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan

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, (339)
"Amazing ocean front and boardwalk access. "
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, (1291)
"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."
The price is AU$169
includes taxes & fees
28 Oct - 29 Oct
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!"
Ocean Terrace Family Apartments
Deluxe Cottage | Private kitchen
Shore Point Cottages
Shore Point Cottages
3.0 star property
9.4 out of 10, Exceptional, (296)
"Was a great place to bring kids and dogs! "
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."
Boardwalk One
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"
The price is AU$227
includes taxes & fees
19 Oct - 20 Oct
The Mallard Apartments
Exterior
Saint Tropez
Saint Tropez
3.0 star property
9.2 out of 10, Wonderful, (123)
"The stay was perfect, so close to the beach, clean and exactly what we needed. "
Saint Tropez
Balcony view
Monte Carlo Condos
Monte Carlo Condos
3.0 star property
6.8 out of 10, (57)
"The room was clean; however the balcony was disgusting. It was covered with pigeon feces and an opening in the ceiling was where many roosted overnight. The door was difficult to open due to rusting and an open area to the outside. The stair door for exit outside the room would not close and the wind caused havoc all night as wind was 27 mi per hour. The indoor pool was not heated and the weather was very cool. I have photos of these complaints."
Monte Carlo Condos
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. "
Club Ocean Villas II
Fridge, microwave, oven, stovetop
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
9.8 out of 10, Exceptional, (118)
"We had nice stay at this property. It was clean and the owner was very nice to deal with. "
The price is AU$493
includes taxes & fees
20 Oct - 21 Oct
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (121)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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. "
OCHG Sand Dollars
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. "
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)
High Point North Studio M8
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, (139)
"Very good time! Property was accurate to listing. "
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15
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!"
The price is AU$417
includes taxes & fees
28 Oct - 29 Oct
Station House East: Upscale Loft in the Historic District Cambridge, MD
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 "
Chesapeake Bay House with Dock & Private Beach
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, (265)
"Property was cleaned and the location is exceptional. We had a wonderful stay."
ON TOP FLOOR OF MARRIOTT - Luxury Boardwalk/Beach 1400 sq ft + Hotel amenities
Premium Condo, Balcony, Bay View | Balcony
Bay Club Resort by Coolvacay
Bay Club Resort by Coolvacay
3.0 star property
8.4 out of 10, Very good, (39)
"One of the cleanest places I’ve stay at loved it ! "
Bay Club Resort by Coolvacay
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"
Americana Condos 10th street
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

Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

10/10 Excellent
"Hotel was wonderful but weather put a damper on fun"
Enoch 3-night trip
Posted 6 hours ago
Carousel Resort Hotel & Condominiums

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$169 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. 

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