Eastern Maryland holiday rentals

We found 11,424 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Eastern Maryland

Showing deals for:11 Dec - 18 Dec

Exterior
Kitchen
Kitchen
Kitchen
Exceptional
(30 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

11% off
AU$2,871
for 7 nights, 1 room
AU$410 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Living area
Interior
Interior
Exterior
Exceptional
(128 reviews)

Chesapeake Bay Waterfront Cottage. Unobstructed water view, Water Access

Earleville

8% off
AU$2,970
for 7 nights, 1 home
AU$424 per night
includes taxes & fees
Chesapeake Bay Waterfront Cottage. Unobstructed water view, Water Access
Dining
Exterior
Interior
Living area
Exceptional
(47 reviews)

Waterfront Retreat for Weekends and More!

Elkton

19% off
AU$3,874
for 7 nights, 1 home
AU$553 per night
includes taxes & fees
Waterfront Retreat for Weekends and More!
Beautiful Sunsets!  No filters!
Property grounds
Interior
Interior
Exceptional
(93 reviews)

Bonfire by the Creek

North East

27% off
AU$2,009
for 7 nights, 1 home
AU$287 per night
includes taxes & fees
Bonfire by the Creek
Exterior
Aerial view
Aerial view
Exterior
Exceptional
(67 reviews)

Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay

Cambridge

8% off
AU$10,877
for 7 nights, 1 home
AU$1,554 per night
includes taxes & fees
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Entrance from inside.  Half bath on first floor is the door on the left.
Favorite night spot for my extended family, when we are there
Yet another nice spot to spend an evening
Sunroom 1/2 - Great view of pond, Bay in distance. So much wildlife to see.
Exceptional
(213 reviews)

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

Stevensville

19% off
AU$4,380
for 7 nights, 1 home
AU$626 per night
includes taxes & fees
240' Private Beachfront @Kent Island Love Point - Great for Families
Dining
Exterior
Property grounds
Room
Exceptional
(11 reviews)

Cozy 1-bedroom bungalow in quaint Darlington with AC

Darlington

18% off
AU$1,219
for 7 nights, 1 home
AU$174 per night
includes taxes & fees
Cozy 1-bedroom bungalow in quaint Darlington with AC
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
Convenient open-concept design:  kitchen, dining and living areas
Delightful front garden welcomes you when approaching house from driveway
Exceptional
(163 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
AU$3,113
for 7 nights, 1 home
AU$445 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Property grounds
Exterior
Dining
Living area
Exceptional
(25 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman

8% off
AU$4,107
for 7 nights, 1 cottage
AU$587 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Outdoor dining
Living area
Private kitchen
Dining
Exceptional
(35 reviews)

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

8% off
AU$5,093
for 7 nights, 1 home
AU$728 per night
includes taxes & fees
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Exterior
Private kitchen
Living area
Room
Exceptional
(31 reviews)

Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

Berlin

7% off
AU$2,925
for 7 nights, 1 home
AU$418 per night
includes taxes & fees
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
Private kitchen
Property grounds
Living area
Room
Exceptional
(31 reviews)

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

Easton

8% off
AU$3,842
for 7 nights, 1 home
AU$549 per night
includes taxes & fees
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
Eating area in panelled Family Room. Eat here, in dining room, or on porch!
St. Michaels Harbor from Park down street
Park half block from house
Front and side view of Blades House from Locust St.
Exceptional
(150 reviews)

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St. Michaels

8% off
AU$5,348
for 7 nights, 1 cottage
AU$764 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Kitchen
Kitchen
Living Room
Coffee Station
Exceptional
(89 reviews)

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Chestertown

17% off
AU$3,109
for 7 nights, 1 home
AU$444 per night
includes taxes & fees
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Property grounds
Interior
Freshly fallen snow on the barn
bedroom with full size bed
Exceptional
(29 reviews)

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

Darlington

18% off
AU$1,302
for 7 nights, 1 home
AU$186 per night
includes taxes & fees
The Chalet is located in the woods of a gated property with a covered porch.
Outdoor dining
Pool
Private kitchen
Property grounds
Exceptional
(217 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville

12% off
AU$4,599
for 7 nights, 1 room
AU$657 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Dining
Interior
Living area
Living area
Exceptional
(53 reviews)

10 minute walk to the beach! Family- size condo

Ocean City

8% off
AU$2,084
for 7 nights, 1 apartment
AU$298 per night
includes taxes & fees
10 minute walk to the beach! Family- size condo
Private kitchen
Living area
Living area
Beach
Exceptional
(57 reviews)

Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!

Ocean City

7% off
AU$7,521
for 7 nights, 1 apartment
AU$1,074 per night
includes taxes & fees
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Living area
Property grounds
Exterior
Dining Room
Exceptional
(111 reviews)

Direct Oceanfront 3 bedroom condo perfect for family and friends with pools

Ocean City

7% off
AU$2,191
for 7 nights, 1 apartment
AU$313 per night
includes taxes & fees
Direct Oceanfront 3 bedroom condo perfect for family and friends with pools
Living area
View from the Kitchen and living room. Back Deck
Private kitchen
Living area
Exceptional
(30 reviews)

SERENE WATER VIEWS-Relaxing family beach house

Ocean City

8% off
AU$5,013
for 7 nights, 1 home
AU$716 per night
includes taxes & fees
SERENE WATER VIEWS-Relaxing family beach house
Private kitchen
Great sunset views of the bay!
Property grounds
Nice fireplace with 50” flatscreen tv above
Exceptional
(147 reviews)

BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!

Ocean City

7% off
AU$1,993
for 7 nights, 1 apartment
AU$285 per night
includes taxes & fees
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
Exterior
Super clean , fun condo to stay in
Breathtaking nighttime views!
Watch the waves, play games, watch tv! All the comforts of home !
Exceptional
(112 reviews)

Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!

Ocean City

7% off
AU$2,143
for 7 nights, 1 apartment
AU$306 per night
includes taxes & fees
Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!
LIVING ROOM
LIVING ROOM
Indoor Pool
MASTER BEDROOM
Exceptional
(95 reviews)

ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH

Ocean City

8% off
AU$3,215
for 7 nights, 1 apartment
AU$459 per night
includes taxes & fees
ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH
Beautiful ocean views
Kitchen with all major appliances and 2-seat breakfast bar
Diamond Head - less than a half block to the beach and close to many OC attractions
Welcome to Diamond Head 305 - 1 bedroom, 1.5 bathroom oceanview with building pool
Exceptional
(14 reviews)

Private Pool Steps From the Beach

Ocean City

7% off
AU$1,740
for 7 nights, 1 apartment
AU$249 per night
includes taxes & fees
Private Pool Steps From the Beach
  • 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:

  • St. Michaels Winery (19.5 mi / 31.4 km)
  • Queenstown Harbor Golf (23.2 mi / 37.3 km)
  • Hooper's Landing Golf Course (14.7 mi / 23.6 km)
  • Layton's Chance Vineyard and Winery (18.4 mi / 29.6 km)
  • Cassinelli Winery and Vineyards (27.1 mi / 43.7 km)
  • Paul Reed Smith Guitars (29.3 mi / 47.1 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)
  • 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)
  • Northern Chesapeake Bay (29.8 mi / 48 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.

More holiday ideas