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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...
View from our Balcony
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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)
Chincoteague Island Virginia Vacation Rentals - Home
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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
Tell us about your group for a quote: Unpublished Specials are available on Chincoteague Waterfront Vacation Rental - Spinnaker, The PonyIsland House Bring your boat - private use of our dock 24/7! Great from...
(18) Excellent (18 reviews)
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
Beautiful Bay Front Condo With Amazing Water Views Booking Summer 2016 Unit 213 - 'sunset In Paradise' Please See Vhr 238542 'another Day In Paradise' For Our 1st Floor Unit Unit 213 Has 3 Bedrooms, ...
(1) Excellent (1 review)
Cape Charles Virginia Vacation Rentals - Home
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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...
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
Air Conditioning • TV (Cable/Satellite) • TV (Antenna)
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 Summer 2016 Unit 103 - 'another Day In Paradise' Unit 213 - 'sunset In Paradise' 2nd Floor Unit See Vhr #238543 Unit 103 Has 3 Bedrooms, 2 Bat...
Pungoteague Virginia Vacation Rentals - Home
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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 - Home
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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...
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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 • DVD Player
5476 Pearl Drive- Oyster Bay I Lovely home located in private community with water view and next to boat ramp. WiFi Available. Bed Sizes: 2 Queen, 2 Twin, 1 Queen Sleep Sofa RatesPrime Season: $1000 weekly/$200 per nig...
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Chincoteague Island Home
3 BR / 3 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
Dishwasher • TV (Antenna) • Private Pool
7136 Silver Sails Landing Spacious duplex overlooking the wetlands. With screen porch, deck, first floor master suite, enjoy the community pool after a long day at the beach! Next door to Bay Pony. Bed Sizes: 2 King,...
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Chincoteague Island Apartment
2 BR / 1 BA / Sleeps 6 2 6 Min stay varies
Apartment / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
Microwave • Air Conditioning • DVD Player
Do you need a vacation rental where you can park your boat and bring your pet? You've found it! Sea Tag #23 is a great two bedroom unit located at 7482 Eastside Drive. The upper level of this home has 1 double bed and 4...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
7718 East Side road One of East Side's most popular rentals! Features include open floor plan with waterside balcony downstairs, and a spacious third level master bedroom suite with private waterside balcony. All level...
Chincoteague Island Virginia Vacation Rentals - Apartment
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Chincoteague Island Apartment
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Apartment / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
6321 Captian's Lane. Beautiful Villa 319 offers a premier location with five- star amenities. This immaculate top floor corner villa is spacious and accommodating, featuring 3 bedrooms. The master bedroom suite has a pr...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
8152 Marsh Point Lane. This lovely vacation rental home features 3BR/2BA (2Q/D/T), central air, screened porch, out door shower (hot & cold) and a nice open floor plan. There is a full line of amenities including cent...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
2 BR / 3 BA / Sleeps 4 2 4 Min stay varies
Home / 2 Bedrooms / Sleeps 4
2 bedrooms 3 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
6388 Teal Lane, Unit 9 Formerly known as Z & T Beach House, this Charming Town Home has 1D, 2T. You will be with in Walking Distance to Maddox Blvd and Beach Road. After a day of Fun and Sun on the Beach, come back a...
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 • DVD Player
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
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Chincoteague Island Home
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
7142 Silver Sails Landing. (2Q, 2T, QSS). This wonderful 3 bedroom/2. 5 bath rental home is light, bright & airy. Adam's Apple (formerly known as Silver Sails) boasts all amenities including community pool privileges,...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
2 BR / 3 BA / Sleeps 5 2 5 7 night min stay
Home / 2 Bedrooms / Sleeps 5
2 bedrooms 3 bathrooms Sleeps 5
Dishwasher • TV (Cable/Satellite) • TV (Antenna)
6153 Marsh Island Drive- Marsh Island The owners of this new vacation rental have taken special care to provide their guests with many extras, including 1 person kayaks, beach items and a crab pot for your use. The vie...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Beautiful home in quiet piney island located at 5408 Oak Drive. Enjoy a game room for all ages. Step inside this home and you will be surprised to see a modern interior with white walls and carpeting. The living room is ...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Lovely 3 bedroom Piney Island home with all amenities & great views located at 7138 Piney Island Road. This home has its 3rd bedroom on the second level. Enjoy lots of space and a huge screened porch. The first bedroom h...
Chincoteague Island Virginia Vacation Rentals - Apartment
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Chincoteague Island Apartment
1 BR / 1 BA / Sleeps 4 1 4 Min stay varies
Apartment / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Microwave • Air Conditioning
7482 East Side Drive. This great 1BR waterfront condo overlooks Assateague Island and lighthouse. Your rental includes use of a private deep water boat slip all week. So bring your boat and leave it in the water! Nicely...
Chincoteague Island Virginia Vacation Rentals - Home
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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
Very nice 3 bedroom ranch home in a cool and shady spot located at 3086 Ridge Road. This home features 1 queen bed, 1 double bed, 1 twin bed, and 1 twin trundle bed. There is 2 dining table that sit a total of 8 peopl...
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 • TV (Cable/Satellite) • 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
1 / 15

Chincoteague Island Home
4 BR / 2 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
7005 Pine Drive Southern Exposure is nestled along the natural shorline of Little Oyster Bay, offering some of the most beautiful water views on Chincoteague Island. Conveniently located in one of Chincoteague's most po...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
2 BR / 3 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
This is a lovely 2 bedroom townhome with gorgeous water views of the Assateague Island. This home will accommodate up to 6. There is a queen sized bed, a double sized bed, and 2 twin sized beds. This home features a fu...
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 • DVD Player
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
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Chincoteague Island Home
2 BR / 1 BA / Sleeps 4 2 4 7 night min stay
Home / 2 Bedrooms / Sleeps 4
2 bedrooms 1 bathroom Sleeps 4
Dishwasher • Microwave • TV (Antenna)
5420 Cedar Drive- Piney Island Cozy home nestled among the pine trees and close to the beach. There is water access for canoe or kayak. Pet friendly! (small dogs only) All bedrooms on same level Bed Sizes: 1 King, 2 Tw...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
2 BR / 2 BA / Sleeps 7 2 7 Min stay varies
Home / 2 Bedrooms / Sleeps 7
2 bedrooms 2 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
7312 Turlington Lane. Charming 2 bedroom ranch home located on East Side! Central air, washer/dryer, dishwasher- " First Time" has it all. Newly remodeled kitchen, brand new wood floors, new dining room & more. Publ...
Chincoteague Island Virginia Vacation Rentals - Home
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Chincoteague Island Home
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Microwave • Air Conditioning
This charming aged home is located at 3438 Main Street. This home is a beach property and has views of the ocean from the backyard. The living room has hardwood floors, a sofa and a chair. The kitchen has pine cabinetry...
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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.