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Spinnaker Waterfront Home from the Water
1 / 22

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
Great Rates Fall weekends Thanksgiving, Christmas & New Years Holidays! Please inquire for Correct Quote - - Save - Book at 2016 rates for all 2017 dates! 2017 rates are not yet published! Tell us about your group f...
(18) Excellent (18 reviews)
Chesapeake Dream from Tazewell Avenue
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Cape Charles Home
4 BR / 3.5 BA / Sleeps 11 4 11 Min stay varies
Home / 4 Bedrooms / Sleeps 11
4 bedrooms 3.5 bathrooms Sleeps 11
High Speed Internet • Dishwasher • Microwave
Chesapeake Dream is a restored three- story (3200 sq. feet) Victorian Four Square built in 1912 on a fenced double lot, ONLY FOUR HOUSES FROM THE BEACH! There are 4 bedrooms, 3 1/2 baths, 2- zone central heat and ai...
Chincoteague Island Virginia Vacation Rentals - Home
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 • DVD Player
Eagle's View is a luxury vacation rental overlooking the Assateague Island Channel and lighthouse. Fully equipped for comfort and convenience, this house is your home base for quick access to beaches, Eastern Shore att...
First Mate Quarter's with water view
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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
Entering onto the property from the Co. Road you will realize you hit a home run for peace and quite. Situated on a large parcel in the middle of the Eastern Shore you will see that you are actually on a penisula. Coming...
(13) Excellent (13 reviews)
Chincoteague Island Virginia Vacation Rentals - Condo
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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
A total remodel of this 2 bedroom, 1 bath condo has just been completed! We purchased this older condo and decided to totally remodel it because of the spectacular views. Everything is new ... new walls to new ...
(1) Excellent (1 review)
Relax by the water...
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Chincoteague Island Cottage
2 BR / 1 BA / Sleeps 6 2 6 Min stay varies
Cottage / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
TV (Antenna) • Air Conditioning • TV (Cable/Satellite)
THE BEST LOCATION on the island! Our waterfront cottages are located on Chincoteague Island and the property overlooks Assateague Island. The location has a beautiful view of The National Park and the Wildlife Refuge. Y...
Chincoteague Island Virginia Vacation Rentals - Condo
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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
Beautiful Bay Front Condo With Amazing Water Views Booking Late Summer & Fall Unit 103 - 'another Day In Paradise' Unit 213 - 'sunset In Paradise' 2nd Floor Unit See Vhr #238543 Unit 103 Has 3 Bedrooms,...
(1) Excellent (1 review)
Chincoteague Island Virginia Vacation Rentals - Condo
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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
Beautiful Bay Front Condo With Amazing Water Views Booking Late Summer & Fall Unit 213 - 'sunset In Paradise' Please See Vhr 238542 'another Day In Paradise' For Our 1st Floor Unit Unit 213 Has 3 Bedr...
(1) Excellent (1 review)
View From Master Bdrm. Bed
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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's Quarters Offers 'One of the BEST Waterfront Views in the Villas' ... Read our Guest's Comments for example 'We have stayed in other units here, but this one is surely the best of the bunch. The view is ama...
(2) Excellent (2 reviews)
Chincoteague Island Virginia Vacation Rentals - Home
1 / 11

Chincoteague Island Home
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Microwave • TV (Antenna)
3402 Ridge Road Lovely 2BR, 1. 5 bath, water view duplex, overlooks Assateague Island with great views for the Pony Swim. Sea MIst is adjoined by its sister unit, Sea Treasure, and each unit sleeps 6. Best way to wa...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 4

Chincoteague Island Home
4 BR / 2 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
Dishwasher • Microwave • TV (Antenna)
6559 Church Street Island home with large back yard and deck and Internet. Pet Friendly! Next door is Lynnwood. 2 bedrooms and 2 baths downstairs/2 bedrooms upstairs Bed Sizes: 1 Queen, 1 Double, 4 Twin RatesPrime Sea...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
Dishwasher • Microwave • TV (Antenna)
5416 Oak Drive- Piney Island Tucked away in Piney Island, spacious and bright interior very private setting. Water access for canoe or kayak. Very close to Assateague Island. Pet Friendly, Wifi and gas grill. - All be...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 15

Chincoteague Island Home
3 BR / 2 BA / Sleeps 6 3 6 Min stay varies
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
This large beach home is right on the water. This home features a large deck that overlooks the bay. Step inside this home and you will find an open floor plan with many windows, high ceilings and white walls. The livin...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 9

Chincoteague Island Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
Dishwasher • Microwave • TV (Antenna)
3241 Mulberry Lane Immaculate waterview home with super large screen porch. It has a great kitchen for cooking large meals. This home is in a nice, quiet location that sits at the end of a cul- de- sac and is in walking...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 11

Chincoteague Island Home
5 BR / 2 BA / Sleeps 10 5 10 7 night min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 2 bathrooms Sleeps 10
Dishwasher • Microwave • TV (Antenna)
3849 Main Street Charming and spacious island home offering a first floor bedroom and Outside Shower. Close to center of town, near restaurants, shopping and nightly entertainment. 1 Bedroom & 1Bath downstairs/3 Bedroo...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
4 BR / 2 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
Dishwasher • Microwave • TV (Antenna)
7503 Pony Cove Lane This affordble duplex is off the beaten path and has room for the whole family! With four bedrooms and two baths! And Wireless Internet. This property has a 3 night minimum Bed Sizes:2 Queen, 4 Twi...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Microwave • TV (Antenna)
7071 Bond Street Tastefully decorated townhouse with many new appliances, screen porch and convenient in town location. 2 bedrooms and 1 bath downstairs/1 bedroom and 1 bath upstairs Bed Sizes: 1 King, 1 Double, 2 Twi...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
4 BR / 2 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
Dishwasher • Microwave • TV (Antenna)
4560 Shelley Cove Lane - Smugglers Cove Private, secluded neighborhood. Very natural wooded setting with water access available. Next door to Pine Cove Place and Serenity Now. Water access is for kayaks and canoes. The...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 12

Chincoteague Island Home
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Microwave • TV (Antenna)
6368 Pine Drive- Piney Island Brand new Piney Island home. Spacious design open and bright with large screened porch and two covered porches offer views of Assateague in the distance. Close to Edie's Folly. Updated photo...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 16

Chincoteague Island Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
Dishwasher • Microwave • TV (Antenna)
5165 Winder Lane Enjoy the sunsets from this new waterfront home, tucked away off North Main Street. Private setting and pet friendly(2 pet maximum). Water access for kayaks and canoes 2 bedrooms and 1 bath downstairs/1...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 9

Chincoteague Island Home
2 BR / 3 BA / Sleeps 7 2 7 7 night min stay
Home / 2 Bedrooms / Sleeps 7
2 bedrooms 3 bathrooms Sleeps 7
Dishwasher • Microwave • TV (Antenna)
6317 Teal Lane Affordable Getaway. Great Location, walk to restaurants, ice cream parlors and amusements. Pet Friendly! Pets limited to 50 pounds and No Cats Please. WiFi Available. Bed Sizes: 1 Queen, 1 Twin, 1 Set...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 8

Chincoteague Island Home
2 BR / 3 BA / Sleeps 7 2 7 7 night min stay
Home / 2 Bedrooms / Sleeps 7
2 bedrooms 3 bathrooms Sleeps 7
Dishwasher • TV (Antenna) • Air Conditioning
Eastwinds 4432 This comfortable townhouse is a great value! It offers two screened porches and spacious rooms. Bed Sizes: 1 King, 1 Queen, 1 Twin, 1 Double Sleep Sofa RatesPrime Season: $750 weekly/ $150 per nightOff...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 10

Chincoteague Island Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
Dishwasher • Microwave • TV (Antenna)
8172 Marsh Point Lane Charming, traditional island home near town. Walking distance to shops, restaurants, waterfront. Perfect for gathering family/ friends. 1 bedroom and 1 bath downstairs/2 bedroom and 1 bath upstai...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 8

Chincoteague Island Home
3 BR / 2 BA / Sleeps 10 3 10 7 night min stay
Home / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
Dishwasher • Microwave • TV (Antenna)
6303 Chester Park Well appointed home located in quiet neighborhood offers first floor bedroom and bath. Offers internet access! ! Bed Sizes: 2 Queen, 2 Sets of Bunks(Twin on top/Double on Bottom), 1 Queen Sleep Sofa ...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 10

Chincoteague Island Home
3 BR / 3 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
Dishwasher • Microwave • TV (Antenna)
7469 Goose Lane Very private and spacious waterfront home overlooking Assateague Island with pier and deep water dock. It offers over 1100 square feet of outside decking and large screen porch and over one acre prime wat...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 14

Chincoteague Island Home
4 BR / 3 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
Dishwasher • Microwave • TV (Antenna)
7142 Pine Drive- Piney Island Lovely home in Piney Island offers views of Assateague Island and water access. Perfect for a large family. Community boat launch area great for kayakers. Bed Sizes: 1 King, 1 Queen, 4 Twi...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 14

Chincoteague Island Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
Dishwasher • Microwave • TV (Antenna)
6317 Highland Park Drive Bring your kayaks and kids! This is a bright tastefully decorated rancher! Playset in backyard for small children, located in quiet neighborhood and in walking distance of restaurants and attr...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 6

Chincoteague Island Home
2 BR / 1 BA / Sleeps 5 2 5 7 night min stay
Home / 2 Bedrooms / Sleeps 5
2 bedrooms 1 bathroom Sleeps 5
TV (Antenna) • Air Conditioning • Balcony
6204 Poplar Street Island Cottage has a great in town location! Easy walk to historic downtown's shops and retaurants. Perfect for a budget frienldy vacation. Pet frienldy (small dogs under 35lbs). Has WiFi. Bed Sizes: ...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 7

Chincoteague Island Home
2 BR / 3 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 3 bathrooms Sleeps 6
Dishwasher • Microwave • TV (Antenna)
4473 Deep Hole Road This wonderful duplex has all the amenities you'd want including LOCATION! ! Just off Maddox Blvd., you have easy accessand walking access to everything! Bed Sizes: 1 Queen, 2 Twins, 1 Queen Slee...
Chincoteague Island Virginia Vacation Rentals - Home
1 / 10

Chincoteague Island Home
2 BR / 3 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 3 bathrooms Sleeps 6
Dishwasher • Microwave • TV (Antenna)
7175 Bunting Road Totally upgraded townhome with large back enclosed sun porch. Nice wetland view! 2 Bedrooms and 2 baths upstairs Has WiFiBed Sizes: 1 King, 1 Queen, 1 Queen Sleep Sofa, 1 Twin Rollaway, 1 Twin Slee...
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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.

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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.

Climate

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.

Events

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.

Food

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.