Eastern Shore Vacation Rentals

144 Rentals

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Ocean City Maryland Vacation Rentals - Condo

Studio / 1BA - Sleeps 4 - Ocean City Condo

THE BEST OF FALL One of the very best features of our oceanfront studio is that when you stand on our...

$86 - $125 / nt

16 Reviews
St Michaels Maryland Vacation Rentals - Cottage

3BR / 3BA - Sleeps 6 - St Michaels Cottage

You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that...

$280 - $495 / nt

11 Reviews
Ocean Pines Maryland Vacation Rentals - Home

4BR / 3BA - Sleeps 11 - Ocean Pines Home

This beautifully appointed 4 bedroom, 3 bathroom home on a 1/4 acre wooded lot in North Ocean Pines...

$125 / nt

Ocean City Maryland Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Ocean City Home

Beautiful bayside waterfront individual home overlooking acres of protected marshlands and wildlife....

$300 - $350 / nt

9 Reviews

3BR / 3BA - Sleeps 10 - Ocean City Condo

Beautiful 1800 square foot ocean side condo in Ocean City Maryland with three large bedrooms and three...

$125 - $295 / nt

18 Reviews
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Grace

2BR / 2BA - Sleeps 6 - Ocean City Condo

Great Ocean Front 2 BR 2 Bath Condo... Pool Tennis, Game Room, Exercise Room, Steps to the Beach....

$175 - $300 / nt

3 Reviews
Direct Ocean Front Balcony
Grace

3BR / 2BA - Sleeps 6 - Ocean City Home

Oh here is a beauty! Spacious 3 Bedroom 2 Bath, Fully Equipped Condo... Kitchen with Granite Countertops...

$300 - $500 / nt

1 Review
Ocean City Maryland Vacation Rentals - Condo

2BR / 2BA - Sleeps 8 - Ocean City Condo

Fantastic home right on the beach! 'Virtual' Home Tour just click on the link at the bottom of this...

$93 - $329 / nt

11 Reviews
Great porches for great views!
Dawn

3BR / 3.5BA - Sleeps 8 - St Michaels Home

Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes...

$250 - $450 / nt

4 Reviews
Ocean City Maryland Vacation Rentals - Condo
Randy

2BR / 2BA - Sleeps 8 - Ocean City Condo

We just had the place freshly painted and new carpeting will be installed the 1st week of February 2013....

$100 - $300 / nt

40 Reviews
Ocean City Maryland Vacation Rentals - Townhouse

4BR / 3.5BA - Sleeps 14 - Ocean City Townhouse

Are you looking to spend your next vacation in a spacious rental with many of the amenities of home?...

$300 - $400 / nt

17 Reviews
Ocean City Maryland Vacation Rentals - Condo

3BR / 3BA - Sleeps 8 - Ocean City Condo

Make our condo your home away from home! We are handicap accessible. Enjoy a week at our family owned...

$111 - $411 / nt

19 Reviews
St Michaels Maryland Vacation Rentals - Home

5BR / 4BA - Sleeps 10 - St Michaels Home

Tidewater Vacations of St Michaels presents a historic, charming vacation rental just minutes from Easton...

$1,000 / nt

Ocean City Maryland Vacation Rentals - Condo

2BR / 2BA - Sleeps 8 - Ocean City Condo

Oceanfront large 3rd floor balcony with patio furniture, 2 bedroom, 2 bath, washer/dryer, free high...

$175 - $200 / nt

Ocean City Maryland Vacation Rentals - Condo
Grace

2BR / 2BA - Sleeps 10 - Ocean City Condo

Direct ocean front 2 BR 2 Bath condo located in the Irene on 111th St. This condo is beautifully decorated...

$250 - $400 / nt

St Michaels Maryland Vacation Rentals - Home

6BR / 7BA - Sleeps 12 - St Michaels Home

Tidewater Vacations Inc on the Eastern Shore presents another luxurious waterfront vacation home. This...

$1,429 / nt

Ocean City Maryland Vacation Rentals - Condo

3BR / 2BA - Sleeps 8 - Ocean City Condo

Make our condo your home away from home! Enjoy a week at our family owned vacation condominium at 44th...

$104 - $330 / nt

23 Reviews
Ocean City Maryland Vacation Rentals - Condo

3BR / 2BA - Sleeps 8 - Ocean City Condo

Stay in one of Ocean City's premiere Oceanfront Buildings. Great amenities including an indoor pool,...

$140 - $265 / nt

8 Reviews
Ocean City Maryland Vacation Rentals - Condo

2BR / 2BA - Sleeps 5 - Ocean City Condo

Enjoy our beautiful clean Oceanfront condo on the 12th floor at the Antigua, in Ocean City, MD. Fully...

7 Reviews
Ocean City Maryland Vacation Rentals - Home
Linda

4BR / 2.5BA - Sleeps 12 - Ocean City Home

DOWNTOWN (10th Street) OCEAN CITY! St. Louis Manor is a very spacious, clean home on the bayside...

$300 - $429 / nt

Ocean City Maryland Vacation Rentals - Condo

2BR / 2BA - Sleeps 5 - Ocean City Condo

About SURFCASTER 202 Large unit with wrap round balcony looking east with side view of the ocean....

$132 - $286 / nt

Ocean City Maryland Vacation Rentals - Condo

2BR / 2BA - Sleeps 5 - Ocean City Condo

About ATLANTIS 807 Great view from ocean front balcony. Building is close to shopping and restaurants...

$115 - $215 / nt

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Visiting the Eastern Shore of Maryland

While visiting the Eastern Shore, Maryland vacation rentals are popular among tourists, due to their comfort, privacy, and size, particularly when compared to standard hotels. VacationHomeRentals.com has the best selection of economical and comfortable rental properties to fit families of all shapes and sizes. Our listings of Eastern Shore rentals come are for rent by owner and are a wonderful way to make your stay in the area more comfortable. The key is to find the right rental for your family in the right location. When visiting the state of Maryland, there's no place as charming as the Eastern Shore. Whether it's for the blue crabs and seafood or fun times playing in the surf, this is one destination that's perfect for families. Located on the eastern side of the Chesapeake Bay, this region of MD is also known for its culture and hospitality.
Areas within the Eastern Shore of Maryland
The cities in this area provide tourists with a number of options when it comes to accommodations and when considering Eastern Shore rentals, visitors are advised to take into account the activities they plan on incorporating into their stay. When planning a vacation to the area, there are nine counties to consider: Cecil, Caroline, Kent, Dorchester, Somerset, Queen Anne's, Wicomico, Worcester, and Talbot. Certain cities within each of these counties are ideal for those vacationing and offer unique qualities and attractions. A few of the more popular areas for visitors staying in Maryland beach house rentals include: Cambridge, Maryland, Salisbury, Rock Hall, Chesapeake City, St Michaels, Crisfield, and Ocean City.
Sightseeing in the Eastern Shore of Maryland & Things to Do
Tourists who stay in Eastern Shore vacation rentals may plan to do so in or near Ocean City, home to the popular Ocean City Boardwalk and activities, such as boutique shopping, arcades, and carnival rides. In the Somerset county town of Crisfield, visit the J.Millard Tawes Historical Museum, Wellington Beach and Park and, on Labor Day weekend, the annual National Hard Crab Derby & Fair. Families traveling with children will appreciate the Salisbury Zoo and Park in Salisbury, MD and the Chesapeake Bay Maritime Museum, located in St. Michaels; both are a combination of education and fun. Rock Hall is another city that offers plenty of family activities, such as a visit to the Eastern Neck National Wildlife Refuge and Waterman's Museum.
Regional Foods & Dining in the Eastern Shore of Maryland
Seafood is most often associated with the Eastern Shore of Maryland, with blue crabs and striped bass being some of the more popular items for people staying on the Eastern Shore. Maryland vacation rentals with access to many different dining locations, including dockside restaurants and dinner cruises are ideal for families interested in eating out, rather than cooking in their rental. Tasty and traditional regional fare includes fried clam, crab cakes, oyster fritters, and Chicken Chesapeake. For dessert, treat the family to a slice of Smith Island Cake, a seven-layer cake that is also the official cake of Maryland.
Weather and Climate on the Eastern Shore
The average high temperatures for the Eastern Shore of Maryland range from the upper 60s to the upper 80s in the spring and summer. The warmest temperatures of the year occur in the month of July and can reach as high as 90 in cities like Cambridge. The coolest temperatures are in the 30s and 40s, with January being the coldest month and as low as 26 degree Fahrenheit in areas such as Chestertown. Snowfall also varies by location. For example, Salisbury experiences on average 1 day of snow and a little over 3 inches of snowfall while Snow Hill receives roughly 6 days of snow and 11 inches of snowfall.
When to Visit the Eastern Shore Maryland
The summer and fall months are generally the best time of the year to visit the Eastern Shore and peak season begins on Memorial Day; because there are often plenty of tourists in the area, it is also a good time to steer clear of hotels and rent one of the many available Eastern Shore vacation rentals. Although the warmer months may draw the largest crowds to the region, tourists willing to brave the colder months will still find plenty of reasons to appreciate spending time with their families while staying in the vacation rentals in Maryland. Regardless of the season in which you visit, there are always fun, local festivals and events to enjoy, including:
The Waterfowl Festival (November) - Perfect for families that enjoy wildlife and the outdoors, this festival draws approximately 15,000 people annually and offers a variety of vendors and exhibitionists.
Tilghman Day (October) - As an annual festival celebrating Maryland's seafood industry, this event includes oyster shucking and crab picking contests, as well as live music, vendors, and an auction.
WineFest at St. Michaels (April) - A weekend festival that features local wine tastings, regional dishes from area chefs, and a variety of talented artists.
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