Eastern Maryland holiday rentals

We found 11,597 holiday rentals — enter your dates for availability

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Holiday rentals with weekly discounts - Eastern Maryland

Showing deals for:3 Oct - 10 Oct

Exceptional

(47 reviews)

Secluded Waterfront Property on 3 acres with swimming pool and dock.

Bozman, MD

5% off

AU$1,335 per night

includes taxes & fees

Exceptional

(5 reviews)

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville, MD

8% off

AU$490 per night

includes taxes & fees

Exceptional

(5 reviews)

Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Chestertown, MD

17% off

AU$645 per night

includes taxes & fees

Exceptional

(8 reviews)

Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier

Cambridge, MD

8% off

AU$2,354 per night

includes taxes & fees

In-ground pool...and private back yard on Solitude Creek with private pier

Exceptional

(18 reviews)

Waterfront 4 acre home with pool between the towns of St. Michaels & Easton!

Easton, MD

8% off

AU$1,351 per night

includes taxes & fees

Exceptional

(14 reviews)

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Port Deposit, MD

9% off

AU$316 per night

includes taxes & fees

Exceptional

(162 reviews)

Waterfront:Panoramic Views/Hot Tub/ Pool/Sleeps 16 /Early check in/out off seaso

Elkton, MD

9% off

AU$2,661 per night

includes taxes & fees

Exceptional

(22 reviews)

The Chalet is located in the woods of a gated property with a covered porch.

Darlington, MD

18% off

AU$278 per night

includes taxes & fees

Exceptional

(21 reviews)

Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler

Rock Hall, MD

8% off

AU$2,089 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Eastern Maryland

Ocean City Boardwalk

Find the best place to stay - Eastern Maryland

House, pond, property. Private beach and Chesapeake Bay is behind far tree line.

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Sleeps 25 · 5 bedrooms · 3+ bathrooms

Harbour Sails Paradise: Panoramic Waterfront Views, Stunning Sunsets & Sunrises

Sleeps 4 · 1 bedroom · 1 bathroom

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Sleeps 4 · 1 bedroom · 1 bathroom

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Explore the beachside setting in Eastern Maryland

The beaches and surrounding scenery provide a peaceful ambience to your holiday home in Eastern Maryland. Travellers to this walkable city praise the boating, bird watching and seafood restaurants. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Eastern Maryland

Do you want to find attractions to visit in the city? You'll be sure to enjoy Eastern Maryland for its boating and bird watching. Venture out of your holiday home and experience everything that makes Eastern Maryland a fun place to get away to. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Layton's Chance Vineyard and Winery (18.4 mi / 29.6 km)
Harrington Raceway and Casino (18.9 mi / 30.3 km)
St. Michaels Winery (19.5 mi / 31.4 km)
Queenstown Harbor Golf Links (23.2 mi / 37.3 km)
Queenstown Harbor Golf Club (23.2 mi / 37.3 km)
Easton Cycle and Sport (10.9 mi / 17.6 km)

Exploring the beaches and other natural features in Eastern Maryland

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Eastern Maryland. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

Gerry Boyle Park at Great Marsh (16.7 mi / 26.8 km)
Long Wharf Park (16.8 mi / 27.1 km)
Chesapeake Bay Environmental Center (23.9 mi / 38.4 km)
Blackwater National Wildlife Refuge (26.9 mi / 43.3 km)
Eastern Neck National Wildlife Refuge (27.3 mi / 43.9 km)
DE Turf Sports Complex (27.8 mi / 44.7 km)

How to get to and around Eastern Maryland

The nearest airport is in Easton, MD (ESN-Easton - Newnam), located 11.6 mi (18.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 33.9 mi (54.6 km) away.

If you prefer to travel by train, Cambridge Station, Ocean City Station and Edgewood Station are the main stations in the city.

Frequently asked questions

What is the best area to stay in Eastern Maryland when booking a holiday home?

Berlin is among the most popular areas to select a holiday home in Eastern Maryland. Searching for some cool things to see and do in this destination? Don't miss Casino at Ocean Downs and Frontier Town Water Park and Golf.

What is the most popular type of holiday home accommodation in Eastern Maryland?

The most desirable types of holiday homes in Eastern Maryland are condos. Searching for something different? Stayz has plenty of options to match the unique needs of our guests, so you'll see properties in all shapes and sizes. The ideal home away from home is waiting for you --- snap up yours today.

How much does it cost to rent a holiday home in Eastern Maryland?

Season, length of stay and property type are some of the conditions that can influence the price of a holiday home. Simply add your travel dates to find your ideal escape. From quaint country cottages to sprawling villas, all Stayz holiday homes offer terrific value.

How much does it cost to rent a beach house in Eastern Maryland?

The average price for a holiday home by the beach in Eastern Maryland will depend on when you're going and the type and size of property you're looking for. Find prices quickly and easily on Stayz by entering the dates you'll be travelling. Then use the filter tool to pick the number of bedrooms and amenities important to you, such as air conditioning, a pool and WiFi.

What are popular home amenities in Eastern Maryland?

When it comes to home amenities that guests prefer in Eastern Maryland, a dishwasher, a microwave oven and off-street parking options are the most popular. With Stayz holiday homes, you'll find options to fit your taste and style, whether you're on a trip with family members, friends or even pets.

Are there large group holiday homes in Eastern Maryland?

There are 1 ,082 holiday homes in Eastern Maryland that can host a group of 10 or more people. Whether you're organising a holiday with extended family or an event like an anniversary, there's plenty of room to get your group together under one roof.

What are the top attractions for families in Eastern Maryland?

There are loads of cool things to see and do with the family in Eastern Maryland, including:

Jolly Roger Amusement Park
Ocean City Beach
Ocean City Boardwalk

Can I find two-bedroom holiday homes in Eastern Maryland?

Take off with your loved ones and enjoy peace, privacy and comfort in one of the 2 ,207 two-bedroom holiday homes Eastern Maryland has to offer.

Are there holiday homes with WiFi in Eastern Maryland?

You'll have a choice of 1 ,166 holiday homes with WiFi in Eastern Maryland. If you want to disconnect from the world on your holiday, but still need to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Stayz.

How old do you have to be to rent a holiday home in Eastern Maryland?

The minimum age allowed can differ between properties on Stayz, so double-check the rules of the holiday home in Eastern Maryland you want. But in general, it's 16, 18 or 21.

How long can I rent a holiday home in Eastern Maryland for?

It's really down to the Eastern Maryland property. To look over a list of options offering extended stays, simply type your travel dates and number of people into Stayz's search page. You can enjoy having the entire place to yourself, along with home comforts like air conditioning, a fully-equipped kitchen and a backyard to run around in. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.