Vacation rentals in Eastern Shore

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top vacation rentals in Eastern Shore

Coconut Malorie Resort Ocean City, Ascend Collection Hotel

200 59th Street on the Bay Ocean City MD

Free Cancellation

46.78 mi from city center

$87 nightly

$97 total

Jan 11 - Jan 12, 2026

Total with taxes and fees

This aparthotel features a gym and a seasonal outdoor pool. Enjoy the hot tub and perks like free WiFi. Self parking is offered and the front desk is staffed around-the-clock.

Pool

Hot Tub

Majestic Hotel & Apartments

7th St & Boardwalk Ocean City MD

47.58 mi from city center

Get rates

A seasonal outdoor pool, self parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a picnic area, and concierge services are also on offer.

Pool

Air conditioning

Saint Tropez

81st Street Ocean City MD

46.7 mi from city center

Get rates

An outdoor pool, free self parking, and laundry facilities are featured at this apartment. WiFi in public areas is free. A terrace and free newspapers are also provided.

Pool

Kitchen

Shore Point Cottages

9543 Stephen Decatur Hwy Berlin MD

46.14 mi from city center

$124 nightly

$138 total

Dec 13 - Dec 14

Total with taxes and fees

A seasonal outdoor pool is featured at this cottage, along with laundry facilities. Take advantage of the free self parking.

Pool

Kitchen

Club Ocean Villas II

105 120th St Ocean City MD

46.2 mi from city center

Get rates

A marina and an indoor pool are featured at this smoke-free apartment. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like a picnic area and a virtual front desk.

Pool

Hot Tub

Americana Condos 10th street

107 10th St Ocean City MD

47.45 mi from city center

$415 nightly

$461 total

Dec 19 - Dec 20

Total with taxes and fees

An indoor pool, self parking, and free newspapers are featured at this condo. WiFi in public areas is free. A terrace and express check-out are also provided.

Pool

Kitchen

Bay Club Resort by Coolvacay

302 32nd Street Ocean City MD

47.11 mi from city center

Get rates

An indoor pool is featured at this condo resort, along with laundry facilities. Take advantage of the free self parking.

Pool

Kitchen

Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Ocean City MD

47.32 mi from city center

$318 nightly

$353 total

Dec 14 - Dec 15

Total with taxes and fees

A water park and an outdoor pool are featured at this smoke-free condo. Laundry facilities are provided for your convenience.

Pool

Kitchen

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

Ocean City MD

46.75 mi from city center

$278 nightly

$309 total

Dec 14 - Dec 15

Total with taxes and fees

A water park and an outdoor pool are featured at this smoke-free vacation home. Laundry facilities are provided for your convenience.

Pool

Kitchen

Boardwalk One

107 N. Atlantic Avenue Ocean City MD

47.6 mi from city center

Get rates

This aparthotel features a seasonal outdoor pool and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning and laundry facilities are also provided.

Pool

Kitchen

"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

Ocean City MD

46.73 mi from city center

$269 nightly

$298 total

Dec 14 - Dec 15

Total with taxes and fees

A water park and an outdoor pool are featured at this smoke-free vacation home. WiFi in public areas is free. Laundry facilities are provided for your convenience.

Pool

Kitchen

Monte Carlo Condos

1107 N. Baltimore Ave. Ocean City MD

47.49 mi from city center

Get rates

An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. A terrace is also provided.

Pool

Kitchen

Downtown St. Michaels | Porch + Pet-Friendly

Saint Michaels MD

21.52 mi from city center

Get rates

Stay at this apartment in St. Michaels. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina are located nearby.

Kitchen

Washer

DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

Ocean City MD

46.74 mi from city center

Get rates

An outdoor pool is featured at this vacation home, along with laundry facilities.

Pool

Kitchen

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Perryville MD

61.25 mi from city center

Get rates

A water park and a hot tub are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A garden and laundry facilities are also provided.

Hot Tub

Kitchen

Don't see what you're looking for?

See all available properties in Eastern Shore

View all properties

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.

The Best Way to Find your Vacation Rentals in Eastern Shore

How cheap can a vacation rental in Eastern Shore be?

You can find vacation rentals in Eastern Shore for as low as $97 per night.

How do you look for the best vacation rental deals in Eastern Shore with Travelocity?

Travelocity provides the best vacation rental deals in various locations throughout Eastern Shore so you can create the perfect plan for you. You can search and filter by type of property, amenities, neighborhood, price range, number of bedrooms, and more.

Are cancellations free on vacation rentals with Travelocity?

Each vacation rental has its own cancellation policy. It’s essential to understand the terms of your agreement before booking. Most rentals in Eastern Shore can be canceled for free when notifying the property before the cancellation deadline.

What types of vacation rentals are available in Eastern Shore?

Short term rentals come in all shapes and sizes. Choose from properties for a wide range of budgets and types of holidays. Families, couples, outdoor adventurers, and leisure travelers alike will find the perfect place for them. Check out our Eastern Shore vacation apartments to get started building your trip.

What are the benefits of booking a short-term rental in Eastern Shore?

Whether it’s for a summer getaway, a winter excursion, or a routine business trip, Eastern Shore vacation homes are often an excellent choice. You can enjoy group vacations with short term rentals to fit your party size. You might take a romantic weekend for two or plan a family reunion, and all stay under one roof. The options are endless, and you can find them on Travelocity.

Why is Travelocity the best site to find your vacation rental in Eastern Shore?

With Travelocity, all your travel needs are taken care of in one convenient platform. We offer fantastic deals on our large selection of vacation rentals to get you the most savings and rewards back on every booking. Save more when you bundle bookings together, including car rentals, flights, and activities. Here, you can build custom Eastern Shore vacations.

How to cancel your vacation rental with Travelocity?

To cancel your vacation rental, contact the property manager. You can find their contact information in the ‘Itinerary’ section of your Travelocity account. Most properties receive a full refund when you cancel before the cancellation deadline. Policies vary by property, so it’s important to understand the terms before booking. For more information, visit our customer service portal.