Eastern Shore holiday rentals

We found 11,338 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Eastern Shore

Showing deals for:1 Jan - 8 Jan

Living Room
Outdoor dining
Kitchen Island
Interior
Exceptional
(196 reviews)

Chesapeake Bay House with Dock & Private Beach

Elkton

8% off
AU$5,077
for 7 nights, 1 home
AU$725 per night
includes taxes & fees
Chesapeake Bay House with Dock & Private Beach
Exterior
Interior
Living area
Interior
Exceptional
(128 reviews)

Chesapeake Bay Waterfront Cottage. Unobstructed water view, Water Access

Earleville

8% off
AU$3,095
for 7 nights, 1 home
AU$442 per night
includes taxes & fees
Chesapeake Bay Waterfront Cottage. Unobstructed water view, Water Access
Kitchen with peak into living room
Foyer into Living Room
Foyer with stairs to second floor peak into 1st  floor master bedroom
Living Room into Kitchen/Dining
Exceptional
(93 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
AU$6,204
for 7 nights, 1 home
AU$886 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Bedroom 1, with desk and window seat.
View from the porch.  Enjoy ospreys and eagles, sailboats and ships.
Expansive front porch overlooking the Chesapeake Bay and Sassafras River!
New playground, with splash pad, at the park within walking distance.
Exceptional
(59 reviews)

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Betterton

12% off
AU$3,835
for 7 nights, 1 home
AU$548 per night
includes taxes & fees
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Living area
Exterior
Living area
Dining
Exceptional
(48 reviews)

Charming Cottage in Historic Charlestown, MD - Marina & Beach Access

Charlestown

8% off
AU$2,935
for 7 nights, 1 home
AU$419 per night
includes taxes & fees
Charming Cottage in Historic Charlestown, MD - Marina & Beach Access
Exterior
Property grounds
Living area
Room
Exceptional
(108 reviews)

Huge Direct Oceanfront Townhouse with Beautiful Sunrises

Ocean City

7% off
AU$3,446
for 7 nights, 1 home
AU$492 per night
includes taxes & fees
Huge Direct Oceanfront Townhouse with Beautiful Sunrises
Interior
Interior
Living area
Dining
Wonderful
(7 reviews)

Spacious waterfront house in charming Royal Oak with WiFi, AC, dock

Royal Oak

8% off
AU$12,937
for 7 nights, 1 cottage
AU$1,848 per night
includes taxes & fees
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Kitchen
Kitchen
Kitchen
Kitchen
Exceptional
(32 reviews)

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

Stevensville

12% off
AU$3,138
for 7 nights, 1 room
AU$448 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Dining room
New Kitchen 2022
Exterior
Property grounds
Exceptional
(66 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
AU$4,646
for 7 nights, 1 home
AU$664 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
View of St Michaels Harbor from french doors in Living Room, and from Side Patio
View of Side of Harrison House and St. Michaels Harbor from Locust Street
Thomas Harrison House looking from St. Michaels Town Harbor
View of St. Michaels Harbor from Town Park in front of Thomas Harrison House
Exceptional
(146 reviews)

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

St. Michaels

8% off
AU$8,931
for 7 nights, 1 home
AU$1,276 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Private kitchen
Interior
Interior
Exceptional
(67 reviews)

Beachfront living near Seacrets! Don't let this memorable getaway pass you by.

Ocean City

8% off
AU$2,775
for 7 nights, 1 apartment
AU$396 per night
includes taxes & fees
Beachfront living near Seacrets! Don't let this memorable getaway pass you by.
Private kitchen
Exterior
Living area
Room
Exceptional
(93 reviews)

Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.

Ocean City

8% off
AU$3,537
for 7 nights, 1 apartment
AU$505 per night
includes taxes & fees
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
Exterior
Living area
Interior
Dining
Exceptional
(52 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

8% off
AU$9,301
for 7 nights, 1 home
AU$1,329 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Beautiful Sunsets!  No filters!
Property grounds
Dining
Interior
Exceptional
(95 reviews)

Bonfire by the Creek

North East

27% off
AU$2,093
for 7 nights, 1 home
AU$299 per night
includes taxes & fees
Bonfire by the Creek
Private kitchen
Front gardens
Interior
Property grounds
Exceptional
(64 reviews)

Beautiful Retreat Located in Rock Hall - walk to everything!

Rock Hall

13% off
AU$3,300
for 7 nights, 1 home
AU$471 per night
includes taxes & fees
Beautiful Retreat Located in Rock Hall - walk to everything!
06-1Q7A4263
Living area
05-1Q7A4356
ext+deck+vfne
Exceptional
(8 reviews)

Biscayne Bungalow– Coastal Charm Near the Beach

Ocean City

5% off
AU$3,213
for 7 nights, 1 home
AU$459 per night
includes taxes & fees
Biscayne Bungalow– Coastal Charm Near the Beach
Pool
Living area
Private kitchen
Living area
Exceptional
(58 reviews)

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

Ocean City

7% off
AU$7,945
for 7 nights, 1 apartment
AU$1,135 per night
includes taxes & fees
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Delightful front garden welcomes you when approaching house from driveway
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Exceptional
(165 reviews)

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

Sherwood

10% off
AU$3,261
for 7 nights, 1 home
AU$466 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Breathtaking nighttime view from the condo
view from balcony to living area
Ocean Front view of the Pyramid the most unique building on the beach
Relax, Have dinner, Play games, see the ocean!
Exceptional
(103 reviews)

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

Ocean City

7% off
AU$1,948
for 7 nights, 1 apartment
AU$278 per night
includes taxes & fees
Escape to The Ocean! , Ocean Front, Beautiful View, Pool!
Lit Entry Hall to Condo - Front Door on Right.
Winter is a Great Time to Enjoy the Beach!
Bedroom with Two Full-Size Beds & Flat-Screen HDTV
Private kitchen
Exceptional
(31 reviews)

Direct Ocean Front...In The Middle of it All!!!

Ocean City

6% off
AU$5,986
for 7 nights, 1 apartment
AU$855 per night
includes taxes & fees
Direct Ocean Front...In The Middle of it All!!!
Interior
Pool
Outdoor dining
Property grounds
Exceptional
(218 reviews)

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

Stevensville

12% off
AU$4,701
for 7 nights, 1 room
AU$672 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Interior
Pool
Private kitchen
Sports court
Exceptional
(6 reviews)

2BR Condo,Pools & Walk to Beach

Ocean City

8% off
AU$3,156
for 7 nights, 1 apartment
AU$451 per night
includes taxes & fees
2BR Condo,Pools & Walk to Beach
18-1Q7A8770
32-1Q7A8831
45-1Q7A8892
43-1Q7A8882
Exceptional
(7 reviews)

Sunkissed Ocean Haven

Ocean City

6% off
AU$5,037
for 7 nights, 1 apartment
AU$720 per night
includes taxes & fees
Sunkissed Ocean Haven
Room
Exterior
Dining
Interior
Exceptional
(86 reviews)

Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.

Ocean City

8% off
AU$3,537
for 7 nights, 1 apartment
AU$505 per night
includes taxes & fees
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
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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. 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)
  • Talbot Massage (13.8 mi / 22.2 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)
  • Adkins Arboretum (20.7 mi / 33.4 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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