Eastern Shore holiday rentals

We found 11,437 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Eastern Shore

Showing deals for:20 Nov - 27 Nov

Exterior
Interior
Private kitchen
Interior
Exceptional
(127 reviews)

Chesapeake Bay Waterfront Cottage. Unobstructed water view, Water Access

Earleville

8% off
AU$3,018
for 7 nights, 1 home
AU$431 per night
includes taxes & fees
Chesapeake Bay Waterfront Cottage. Unobstructed water view, Water Access
Room
Exterior
Interior
Living area
Exceptional
(47 reviews)

Waterfront Retreat for Weekends and More!

Elkton

19% off
AU$3,983
for 7 nights, 1 home
AU$569 per night
includes taxes & fees
Waterfront Retreat for Weekends and More!
Dining
Property grounds
Beautiful Sunsets!  No filters!
Interior
Exceptional
(92 reviews)

Bonfire by the Creek

North East

27% off
AU$2,041
for 7 nights, 1 home
AU$292 per night
includes taxes & fees
Bonfire by the Creek
Interior
New Kitchen 2022
Dining room
Exterior
Exceptional
(64 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
AU$5,236
for 7 nights, 1 home
AU$748 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
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
(162 reviews)

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

Sherwood

10% off
AU$3,103
for 7 nights, 1 home
AU$443 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Interior
Living area
Exterior detail
Private kitchen
Exceptional
(70 reviews)

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville

8% off
AU$1,971
for 7 nights, 1 cottage
AU$282 per night
includes taxes & fees
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Room
Private kitchen
Dining
Living area
Exceptional
(30 reviews)

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

Berlin

8% off
AU$3,537
for 7 nights, 1 home
AU$505 per night
includes taxes & fees
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
dining room
Exterior
view from balcony overlooking playhouse, pergola and Brooks Creek
two twin beds and play area in loft
Exceptional
(274 reviews)

Family and Pet-Friendly, Waterfront with Pier

Cambridge

8% off
AU$3,197
for 7 nights, 1 cottage
AU$457 per night
includes taxes & fees
Family and Pet-Friendly, Waterfront with Pier
Two bar stools are available at the kitchen bar.
The front porch has ceiling fans to help keep you cool.
Enjoy water views from the dining room and kitchen.
Exterior
Exceptional
(54 reviews)

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

Fishing Creek

7% off
AU$1,907
for 7 nights, 1 home
AU$272 per night
includes taxes & fees
Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly
Pool
Living area
Private kitchen
Living area
Exceptional
(56 reviews)

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

Ocean City

7% off
AU$7,748
for 7 nights, 1 apartment
AU$1,107 per night
includes taxes & fees
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Kitchen / Living Room
Sunroom
Kitchen
Front Porch
Exceptional
(124 reviews)

Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City

Berlin

7% off
AU$1,888
for 7 nights, 1 home
AU$270 per night
includes taxes & fees
Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City
Exterior
Great sunset views of the bay!
Property grounds
Private kitchen
Exceptional
(143 reviews)

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

Ocean City

7% off
AU$2,020
for 7 nights, 1 apartment
AU$289 per night
includes taxes & fees
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
Living area
Property grounds
Beach
Private kitchen
Exceptional
(105 reviews)

Huge Direct Oceanfront Townhouse with Beautiful Sunrises

Ocean City

7% off
AU$3,361
for 7 nights, 1 home
AU$480 per night
includes taxes & fees
Huge Direct Oceanfront Townhouse with Beautiful Sunrises
Living area
Exterior
Dining
Private kitchen
Exceptional
(20 reviews)

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

Tilghman

8% off
AU$4,093
for 7 nights, 1 cottage
AU$585 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds
Pool
Outdoor dining
Private kitchen
Exceptional
(216 reviews)

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

Stevensville

12% off
AU$4,584
for 7 nights, 1 room
AU$655 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Living area
Be ready to float! Bring your own inner tubes  and tennis shoes!
Exterior detail
Interior
Exceptional
(143 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
AU$2,892
for 7 nights, 1 cottage
AU$413 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Private kitchen
Open from Memorial Day weekend through Labor Day
Interior
Living area
Exceptional
(128 reviews)

GorgeousTownhouse,Bay Views, pool, short walk to Ocean, Free WiFi, linens inc.

Ocean City

7% off
AU$4,305
for 7 nights, 1 home
AU$615 per night
includes taxes & fees
GorgeousTownhouse,Bay Views, pool, short walk to Ocean, Free WiFi, linens inc.
Room
View from the Kitchen and living room. Back Deck
Living area
Living area
Exceptional
(30 reviews)

SERENE WATER VIEWS-Relaxing family beach house

Ocean City

8% off
AU$5,194
for 7 nights, 1 home
AU$742 per night
includes taxes & fees
SERENE WATER VIEWS-Relaxing family beach house
Kitchen
Back deck off of bedroom and screened-in deck off of living room.
Dining area and living room
Screened-in deck
Exceptional
(202 reviews)

Gorgeous Renovated Townhouse-MUST BE OVER 25 TO RENT

Ocean City

8% off
AU$2,209
for 7 nights, 1 home
AU$316 per night
includes taxes & fees
Gorgeous Renovated Townhouse-MUST BE OVER 25 TO RENT
Dining
Interior
Living area
Living area
Exceptional
(53 reviews)

10 minute walk to the beach! Family- size condo

Ocean City

8% off
AU$2,112
for 7 nights, 1 apartment
AU$302 per night
includes taxes & fees
10 minute walk to the beach! Family- size condo
Welcome, friends.
Every sunrise brings new hope for a brighter future.
Gather around the table for family dinner.
Star light, star bright, first star I see tonight.
Exceptional
(52 reviews)

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek

8% off
AU$2,796
for 7 nights, 1 cottage
AU$399 per night
includes taxes & fees
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Indoor Pool
LIVING ROOM
ADAGIO UNIT 207
LIVING ROOM
Exceptional
(94 reviews)

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

Ocean City

8% off
AU$3,331
for 7 nights, 1 apartment
AU$476 per night
includes taxes & fees
ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH
Ocean Front view of the Pyramid the most unique building on the beach
view from balcony to living area
Interior
Breathtaking nighttime view from the condo
Exceptional
(101 reviews)

Escape to The Ocean! , Ocean Front, Beautiful View, Pool!

Ocean City

7% off
AU$2,386
for 7 nights, 1 apartment
AU$341 per night
includes taxes & fees
Escape to The Ocean! , Ocean Front, Beautiful View, Pool!
Welcome to Diamond Head 305 - 1 bedroom, 1.5 bathroom oceanview with building pool
Kitchen with all major appliances and 2-seat breakfast bar
Beautiful ocean views
Diamond Head - less than a half block to the beach and close to many OC attractions
Exceptional
(12 reviews)

Private Pool Steps From the Beach

Ocean City

7% off
AU$1,892
for 7 nights, 1 apartment
AU$270 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

Delight in the oceanfront landscape of Eastern Shore

The ocean views and wildlife provide a pleasant backdrop to your holiday home in Eastern Shore. Well known for its sailing, seafood restaurants and bird watching, this walkable city won't disappoint. Maryland Beach and Ocean City Beach are just a couple of the must-see attractions. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Eastern Shore

Do you want to discover things to do in the city? Travellers enjoy fun activities like boating and bird watching. Venture out of your cosy holiday rental and experience everything that makes Eastern Shore a fun spot to go on holiday. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • St. Michaels Winery (21.2 mi / 34.2 km)
  • Salisbury Zoo (25.5 mi / 41.1 km)
  • Queenstown Harbor Golf (28.2 mi / 45.4 km)
  • Layton's Chance Vineyard and Winery (12 mi / 19.3 km)
  • Hooper's Landing Golf Course (12.4 mi / 20 km)
  • Easton Cycle and Sport (13.6 mi / 21.9 km)

Exploring the beaches and other natural features in Eastern Shore

Travellers enjoy Eastern Shore for its seaside and wildlife. Whether you're an active traveller or just want to take in the scenery, Eastern Shore is a great spot to appreciate mother nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Long Wharf Park (12.9 mi / 20.8 km)
  • Gerry Boyle Park at Great Marsh (13 mi / 20.9 km)
  • Blackwater National Wildlife Refuge (21.6 mi / 34.8 km)
  • Pemberton Historical Park (24.5 mi / 39.4 km)
  • Chesapeake Bay Environmental Center (28.1 mi / 45.3 km)
  • Williams Pond Park (14.1 mi / 22.7 km)

Travelling to and around Eastern Shore

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 15.2 mi (24.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 28.7 mi (46.1 km) away.

If you're travelling by train, Cambridge Station, Ocean City Station and Perryville Station are the main stations that serve the city.

Frequently asked questions

What is the best area to stay in Eastern Shore when booking a holiday home?
Among the most popular areas to book your Stayz holiday property in Eastern Shore is Berlin. Make your home away from home here and experience some top attractions, including Casino at Ocean Downs and Frontier Town Water Park and Golf.
What is the most popular type of holiday home accommodation in Eastern Shore?
The most in-demand types of holiday homes in Eastern Shore are condos. Want something different? Stayz has many options to match our guests' requirements, so you'll see properties in all sizes and shapes. The perfect fit is ready and waiting for you — find yours today.
How much does it cost to rent a holiday home in Eastern Shore?
Several things can influence what you'll pay for your holiday home in Eastern Shore, like the time of year, property type and length of stay. However, all Stayz homes have one thing in common — exceptional value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Eastern Shore?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Click on your Eastern Shore travel dates to view your options on Stayz. Did someone just say "hot tub"? Use our filters to choose the amenities and features you need.
What are popular home amenities in Eastern Shore?
When it comes to home amenities that guests are looking for in Eastern Shore, off-street parking options, a dishwasher and a microwave oven are at the top of the list. With Stayz holiday homes, you'll discover options to fit your style and taste, whether you're taking a trip with family, friends or even pets.
Are there large group holiday homes in Eastern Shore?
Eastern Shore has 1 ,031 holiday properties that can cater to 10 or more guests. These properties come with enough space to enjoy good times with your nearest and dearest.
What are the top attractions for families in Eastern Shore?
Keep your kids busy at these popular family-friendly attractions in Eastern Shore:
  • Ocean City Beach
  • Ocean City Boardwalk
  • Jolly Roger Amusement Park
Can I find two-bedroom holiday homes in Eastern Shore?
Gather your nearest and dearest and enjoy peace, privacy and comfort in one of the 2 ,191 two-bedroom holiday homes Eastern Shore has to offer.
Are there holiday homes with WiFi in Eastern Shore?
Eastern Shore has 1 ,138 holiday homes with WiFi, so you'll be able to stay connected while you're travelling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming Hollywood blockbusters to posting pics on social media, these Stayz homes make it a cinch to get online.
How old do you have to be to rent a holiday home in Eastern Shore?
We recommend checking with the Eastern Shore holiday property you're considering on Stayz as the age limit varies. However, typically it's 16, 18 or 21.
How long can I rent a holiday home in Eastern Shore for?
It really depends on the Eastern Shore property. To view all available options offering extended stays, simply type your dates and number of guests into Stayz. Look forward to having the property to yourself, along with the comforts of home like a fully-equipped kitchen and a backyard where your little ones can play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.

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