Eastern Shore Virginia Beach Rentals & Apartments - 310 Rentals Available

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Chincoteague Island Condo
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"This was one of the best rental experiences we have had. We had a wonderful long weekend at the villa. It is a beautiful space and was very comfortable for our family of five. Annie is an excellent host. She provided us with lots of information about ..."
- Jeannie Philips Heimann, Annapolis, MD
(1) Excellent (1 review)
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Pungoteague Home
3 BR / 2.5 BA / Sleeps 6 3 6 Min stay varies
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2.5 bathrooms Sleeps 6
Microwave • Washer/Dryer • Air Conditioning
"We spent 4 days at Randy's Get- Away in the woods on the water, and it was just what the Dr. ordered. Peace and quiet but a great time. My Brother and I really needed some R and R and we received it in large doses here. We were out on the water every..."
- Tammy, Manasquan, NJ
(13) Excellent (13 reviews)
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Chincoteague Island Condo
3 BR / 2 BA / Sleeps 7 3 7 Min stay varies
Condo / 3 Bedrooms / Sleeps 7
3 bedrooms 2 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
"Captain Quarters is absolutely lovely. It is very clean. Everything you need is there except the bed linens and towels. The deck provides a lovely view of the water where we saw dolphins swimming every morning. The pool is great for adults as well as..."
- Brian Rich, Boston,N. Y.
(2) Excellent (2 reviews)
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Chincoteague Island Home
4 BR / 4 BA / Sleeps 11 4 11 Min stay varies
Home / 4 Bedrooms / Sleeps 11
4 bedrooms 4 bathrooms Sleeps 11
High Speed Internet • Dishwasher • Microwave
"We spent Memorial day weekend in this property. We were a group of 10 friends (5 couples) and this home was so comfortable and spacious that we all had plenty of space and didn't feel "on top of each other. The views from all the bedrooms and covered ..."
- Sergio Restaino, Alexandria, VA
(19) Excellent (19 reviews)
1 / 38

Chincoteague Island Home
4 BR / 3.5 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3.5 bathrooms Sleeps 8
High Speed Internet • Microwave • TV (Cable/Satellite)
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Chincoteague Island Condo
2 BR / 1 BA / Sleeps 4 2 4 Min stay varies
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
"Our family had a great mini- vacation in this condo. It was very clean, nicely furnished, and a great place to relax over spring break. We especially enjoyed the views across the channel. The owner was wonderful to work with, and provided everything..."
- Chris Miciek, Philadelphia, PA
(1) Excellent (1 review)
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Chincoteague Island Condo
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"This is the 3rd year I have rented this beautiful condo. Gorgeous sunsets, within walking distance to many places and crab pots! Wonderful memories!"
- Martha Mauro, Buffalo, NY
(2) Excellent (2 reviews)
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Chincoteague Island Home
-1 BR / 2 BA / Sleeps 6 -1 6 Min stay varies
Home / -1 Bedroom / Sleeps 6
-1 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • TV (Antenna)
1 / 10

Chincoteague Island Home
2 BR / 1 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
TV (Antenna) • Microwave • Air Conditioning
1 / 14

Chincoteague Island Home
-1 BR / 2 BA / Sleeps 6 -1 6 Min stay varies
Home / -1 Bedroom / Sleeps 6
-1 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • TV (Antenna)
1 / 14

Chincoteague Island Home
-1 BR / 3 BA / Sleeps 11 -1 11 Min stay varies
Home / -1 Bedroom / Sleeps 11
-1 bedrooms 3 bathrooms Sleeps 11
High Speed Internet • Dishwasher • TV (Antenna)
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About Eastern Shore

Visiting Virginia’s Eastern Shore

With its beautiful beaches, rich history, and unique culture, travelers flock to Virginia’s Eastern Shore for memorable vacations. The Delmarva Peninsula contains the eastern shores of Maryland and Virginia as well as the majority of the state of Delaware. The Eastern Shore of Virginia, however, boasts some of the most exciting and interesting attractions and destinations on the peninsula.
View the wild ponies on the islands of Assateague and Chincoteague. Watch a NASA rocket launch at the Wallops Flight Facility. Relax and enjoy the sand and sun. Finish the perfect day with a delicious seafood dinner and a restful sleep at one of the many family-friendly Eastern Shore rentals, available in abundance online from Vacation Home Rentals. The Eastern Shore of Virginia offers fun for all ages. You won’t be disappointed!

Areas of Virginia’s Eastern Shore

This unique region of Virginia overflows with notable destinations, but a few stand out above the rest. Chincoteague Island represents one of the most beloved destinations for families in this part of Virginia. Eastern Shore vacation rentals are easily obtained on the island. Don’t waste your time and money driving a long distance for a limited day: Find Eastern Shore house rentals from Vacation Home Rentals that are only a short walk or drive from your favorite attractions.
Onancock is another amazing destination in this region of Virginia. Located on the Chesapeake Bay, the town of Onancock offers a delightful variety of dining and activity options while retaining its small-town charm. Eastern Shore, VA, vacation rentals in this area can be found steps away from Onancock’s historic district.
The town of Cape Charles lies near the mouth of the Chesapeake Bay. Families love the relaxing beach on the bay. If you arrive by boat, dock at the Cape Charles marina and enjoy easy access to the town. There are many Eastern Shore homes for rent in Cape Charles. One of these could be the perfect place to rent for a relaxing, laid-back vacation.

Sightseeing in Virginia’s Eastern Shore

No matter where you go, there is much to see and do on the Eastern Shore. Visit the Ker Place museum in Onancock, a Georgian-style mansion built in the late 1700s. In Cape Charles, see a play with a fully local cast at the Historic Palace Theatre. Take a sunset boat tour around Chincoteague and Assateague. You will likely see wild ponies roaming the shorelines. Whether your family wants to experience nature, shop, or relax on a beach, Virginia’s Eastern Shore can deliver.

Dining on Virginia’s Eastern Shore

If you love seafood, the Eastern Shore will stun your taste buds with its extravagant variety of seafood dishes. Get a meal at Etta’s Channel Side Restaurant in Chincoteague, VA. Try the signature dish, flounder stuffed with crab imperial. If you are in Onancock, visit the award-winning restaurant at the Charlotte Hotel. If you want to enjoy a night in at your rental home, pick up some steamed blue crabs freshly caught the same day and feast with your family.

Weather and Climate

Virginia’s Eastern Shore has average winters, and its springs are wet and rainy. During the summer months, expect high humidity and hot days. Yet most Eastern Shore rentals by owner have air conditioning to cool your family off in the summer. Be wary of hurricanes in the late summer and fall months. Check the extended weather forecast before departing for your vacation.

When to Visit

The best time to visit Virginia’s Eastern Shore is during the summer. The summer months allow you and your family to fully experience the beaches, natural wonders, and sights of the region. Save money by visiting during the spring, fall, or winter months. Prices on Eastern Shore vacation rentals are lower during the colder months. During Christmastime, the historic towns are full of local charm and holiday spirit. Visit soon and have the family vacation of a lifetime.


From the porch of your Eastern Shore, Virginia waterfront vacation rental, you'll see an endless expanse of pristine beaches and rolling blue waves. This area covers seaside strips of both Accomack and Northampton counties, each of which offers plenty to keep you busy during your Virginia vacation.

Things to Do

You'll never experience a dull minute on the Eastern Shore of Virginia. Many small towns pepper the coast, providing ample opportunities to shop for knickknacks, artisan goods, jewelry, clothing, and other items. Many shops specialize entirely in sea glass, which means you'll find bottles, glasses, suncatchers, windows, and other items crafted from glass the artists found on the beach.
Since the islands of Chincoteague and Assateague are deeply rooted in Eastern Shore culture, you'll want to take a sunset boat tour of the island. You'll get to see herds of ponies that still live in the brush as well as other wildlife that emerges just before the sun goes down. Then stop in the Museum of Chincoteague to view Misty (from Marguerite Henry's classic children's tale) in all her taxidermied glory.
The Eastern Shore Wine Trail is another must-do adventure. You'll visit (and taste wine) at three separate wineries on the trip, which takes a little over one hour.


Virginia's Eastern Shore gets slightly more rainfall than the U.S. average, but if you visit in late spring or during the summer, you'll likely avoid getting wet. Average temperatures range from the low 20s in January to the low 80s in July, though extremes are possible.


If you visit the Eastern Shore during July, you might catch the Chincoteague Pony Swim (also known as Pony Penning Day), when cowboys and cowgirls round up the ponies on Assateague and "swim" them across the channel to the mainland. The ponies and their foals are auctioned off to benefit the local firefighting agency.
Alternatively, you might want to visit in August so you can attend the Eastern Shore's Own Craft Beer & Music Festival in Belle Haven. Sample craft beers, listen to live music, and eat mouth-watering barbecue. The event benefits a local arts center, which means the $20 ticket price goes to a good cause.


While you might cook a couple meals in your Eastern Shore, Virginia, waterfront vacation rental, make sure to devote at least a few mealtimes to local restaurants. You can't go wrong with seafood prepared by the Island House Restaurant in Wachapreague or The Oyster Farm Seafood Eatery in Cape Charles
If you're in the mood for comfort food, try Mallards at the Wharf in Onancock. It serves an excellent barbecue sandwich as well as crab, oysters, lobster, and other seafood delicacies. For a quick bite in the morning, the Cape Charles Coffee House is the way to go.
Booking an Eastern Shore, Virginia waterfront vacation rental ensures that you'll have a comfortable place to call home when your feet are sore and you're ready to call it a day. Pack your itinerary with some of the suggestions above.