Eastern Shore holiday homes

Why visit Eastern Shore

• Scenic coastal beauty: Enjoy Eastern Shore’s pristine beaches and crystal-clear marinas perfect for sunbathing and water-based adventures.
• Rich local history: Explore engaging museums and historical sites that showcase the area’s vibrant heritage.
• Family-friendly parks: Relax in charming urban parks ideal for picnics and leisurely strolls with the whanau.
• Scenic drives: Take a leisurely road trip through picturesque countryside and coastal routes.
• Warm local hospitality: Experience the welcoming vibe and cultural charm unique to Eastern Shore.

Top attractions near Eastern Shore

Eastern Shore, Maryland, is a picturesque destination perfect for outdoor enthusiasts and families alike. Explore charming urban parks, enjoy the scenic marinas, and delve into local history at engaging museums. Whether you're after stunning beach views or cultural experiences, the Eastern Shore offers a delightful mix of activities that cater to all travellers, making it an ideal spot for a memorable holiday.

• Chesapeake Bay Maritime Museum: This vibrant maritime museum offers an in-depth look at the rich maritime heritage of the Chesapeake Bay, featuring historic vessels, interactive exhibits, and stunning waterfront views.
• St. Michaels Marina: An ideal spot for adventure enthusiasts, this marina provides opportunities for boating, kayaking, and fishing, all surrounded by picturesque coastal scenery.
• The Third Haven Friends Meeting House: A serene historic site, this Quaker meeting house features beautiful architecture and a peaceful garden, perfect for reflection and appreciating local culture.

Things to do recommended for couples

For a romantic getaway on the Eastern Shore, explore the scenic beauty of the Chesapeake Bay by taking a sunset cruise. Enjoy a picnic at the serene beaches of Assateague Island, or wander hand-in-hand through the charming streets of St. Michaels, soaking in the local culture and history.

Things to do recommended for families

Your family will delight in exploring the picturesque beaches of Assateague Island, where wild ponies roam freely, or take a fun-filled trip to the Chesapeake Bay Maritime Museum to learn about local history and marine life.

Things to do recommended for groups

Groups visiting Eastern Shore, Maryland, can explore local seafood shacks and take scenic bike rides along the coast, enjoying the vibrant maritime culture while sampling traditional crab cakes and lively waterfront bars.

What do I need to keep in mind when booking a vacation around Eastern Shore

If you're planning a trip with a group, family, or pets, or if you're interested in longer stays, be sure to use the appropriate filters to match your needs. Here are some helpful Vrbo booking tips for you.

• Traveling to Eastern Shore with a group: Think about how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
• Traveling to Eastern Shore with young kids: Travelling with young kids can be quite demanding. It's important to prioritise their comfort and safety, as well as to seek out suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
• Taking your pets with you to Eastern Shore: For many families, a trip isn't truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and bedding, ensuring that your four-legged family members feel just as comfortable as everyone else.
• Planning for a long term stay visiting Eastern Shore: If you’re searching for holiday rentals that offer great deals for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Eastern Shore

Discover the charming Eastern Shore of Maryland, where family-friendly vibes meet rich history and stunning outdoor scenery. Visitors can enjoy beautiful beaches, scenic drives, and historical excursions, all while experiencing the warm local hospitality. Whether you're after a leisurely coastal holiday or a comfortable retreat amidst natural beauty, Eastern Shore offers a unique blend of relaxation and adventure.

• St. Michaels: St. Michaels is a delightful city offering travellers a rich mix of outdoor adventures and serene coastal experiences. Located a short 14km journey from Eastern Shore, this destination boasts a scenic boardwalk and expansive recreational areas perfect for leisurely strolls and picnics. Visitors can enjoy the gentle charm of its family beach and embrace the stunning bay views, making it an ideal spot for nature enthusiasts and those seeking a relaxed beach escape.
• Oxford: Oxford presents a captivating blend of natural beauty and engaging activities. Also a 14km trip from Eastern Shore, this city is celebrated for its outdoor attractions and vibrant boardwalk. Travellers can explore the local recreational area, enjoy a leisurely day at the beach, or indulge in some shopping at nearby centres. The picturesque bay and family beach add to the allure, offering a perfect mix of relaxation and exploration for those on holiday.
• Wye Island: Wye Island is a naturally enchanting island destination, just a 14km drive away from Eastern Shore. Renowned for its outdoor and scenic appeal, the island provides access to a tranquil recreational area and boasts impressive landmarks such as a national state park, a captivating bay, and a lively marina. This serene setting is perfect for visitors keen to immerse themselves in nature and enjoy a peaceful escape by the water.

Best time to go to Eastern Shore

If you're planning a trip to Eastern Shore, it's a good idea to check both the weather and property rates. The warmest month is July.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	34.2°F (1.2°C)	Light Rain	Mostly Sunny
February	36.9°F (2.7°C)	Light Rain	Mostly Sunny
March	43.7°F (6.5°C)	Light Rain	Mostly Sunny
April	54.3°F (12.4°C)	Light Rain	Mostly Sunny
May	63.7°F (17.6°C)	Light Rain	Mostly Sunny
June	72.1°F (22.3°C)	Light Rain	Mostly Sunny
July	78.3°F (25.7°C)	Light Rain	Mostly Sunny
August	77.7°F (25.4°C)	Light Rain	Mostly Sunny
September	70.9°F (21.6°C)	Light Rain	Mostly Sunny
October	59.2°F (15.1°C)	Light Rain	Mostly Sunny
November	50.9°F (10.5°C)	Light Rain	Mostly Sunny
December	39.9°F (4.4°C)	Light Rain	Mostly Sunny

Booking with Vrbo is simple

Are you hoping to make your next trip more budget-friendly? Being flexible with your travel dates can be a great way to find better prices, as they often fluctuate. Additionally, if you're considering a longer stay, you could enjoy substantial savings. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of holiday rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a dedicated area where you can start planning new adventures, pick up where you left off with your current plans, or keep track of your bookings. Your saved or reserved properties are neatly organised into Potential, Upcoming, or Current Trips. Discover more about Trip Boards by visiting: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.