Eastern Shore Vacation Rentals

284 Rentals

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Cape Charles Virginia Vacation Rentals - Home

4BR / 4BA - Sleeps 12 - Cape Charles Home

Enjoy a relaxing stay only 3 blocks from the beach in the waterside town of Historic Cape Charles. Named...

$199 - $233 / nt

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4BR / 2.5BA - Sleeps 9 - Chincoteague Island Home

State Of the Art Club House With Indoor and Outdoor pools in the development Canel front home. Custom...

$172 - $215 / nt

21 Reviews
Pungoteague Virginia Vacation Rentals - Home

3BR / 2.5BA - Sleeps 6 - Pungoteague Home

Entering onto the property from the Co. Road you will realize you hit a home run for peace and quite....

$250 - $275 / nt

13 Reviews
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4BR / 2BA - Sleeps 10 - Chincoteague Island Home

Charming home nestled in the pine trees on Piney Island located at 7090 Pine Drive. This house has been...

$97 - $136 / nt

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5BR / 3BA - Sleeps 10 - Chincoteague Island Home

4368 Main Street. Wonderful 5 bedroom, 3. 5 bath Victorian home on Main Street, just a short walk from...

$136 - $222 / nt

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3BR / 3BA - Sleeps 8 - Chincoteague Island Home

7158 Piney Island Road, Unit 1 Delightful end- unit townhome overlooking the Assateague Channel and...

$118 - $236 / nt

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3BR / 3BA - Sleeps 8 - Chincoteague Island Home

6425 Pine Drive This beautiful waterfront duplex home is located in the very popular "Piney Island" area,...

$128 - $204 / nt

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3BR / 3BA - Sleeps 8 - Chincoteague Island Home

A very nice contemporary home located in Oyster Bay II at 5426 Pearl Drive. Located next to the community...

$113 - $154 / nt

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3BR / 3BA - Sleeps 8 - Chincoteague Island Home

Ocean East #3 being completely remodeled! ! From the outside decks and railings, to the inside floors...

$118 - $229 / nt

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3BR / 3BA - Sleeps 8 - Chincoteague Island Home

Lovely 3 bedroom Piney Island home with all amenities & great views located at 7138 Piney Island Road....

$108 - $171 / nt

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3BR / 2BA - Sleeps 8 - Chincoteague Island Apartment

6321Captian's Lane COME AND ENJOY! You've earned it. Located on the edge of beautiful Chincoteague Bay,...

$140 - $243 / nt

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3BR / 3BA - Sleeps 8 - Chincoteague Island Home

3050 Main Street. Sunny Daze - this very popular waterfront rental home on South Main Street offers...

$111 - $183 / nt

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2BR / 2BA - Sleeps 8 - Chincoteague Island Home

6254 Wagner Lane. This beautiful 2BR ranch home has a quiet, out- of- the- way location on Little Oyster...

$128 - $200 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Chincoteague Island Home

This charming contemporary ranch is located at 5535 N. Hibiscus Dr. This home has all the bells and whistles,...

$85 - $128 / nt

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2BR / 3BA - Sleeps 6 - Chincoteague Island Home

This is a lovely 2 bedroom townhome with gorgeous water views of the Assateague Island. This home will...

$72 - $133 / nt

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2BR / 1BA - Sleeps 6 - Chincoteague Island Apartment

Do you need a vacation rental where you can park your boat and bring your pet? You've found it! Sea...

$72 - $108 / nt

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2BR / 1BA - Sleeps 6 - Chincoteague Island Home

Cozy farmhouse cottage overlooking Assateague Island located at, 7759 East Side Drive. The first bedroom...

$75 - $100 / nt

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2BR / 2BA - Sleeps 6 - Chincoteague Island Apartment

Cozy 2 bedroom condo located at 7622 East Side Drive. Enjoy a large master bedroom suite with doors that...

$99 - $147 / nt

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3BR / 3BA - Sleeps 6 - Chincoteague Island Home

This charming beach home is perfect for a small family. Enjoy beautiful views of the water right from...

$136 - $193 / nt

Chincoteague Island Virginia Vacation Rentals - Home

2BR / 2BA - Sleeps 6 - Chincoteague Island Home

5250 Pine Tree Way - Agetaway offers you just that - a quiet get away. It's neat, cozy and tucked...

$71 - $108 / nt

Chincoteague Island Virginia Vacation Rentals - Home

2BR / 2BA - Sleeps 6 - Chincoteague Island Home

This charming aged home is located at 3438 Main Street. This home is a beach property and has views of...

$68 - $90 / nt

Chincoteague Island Virginia Vacation Rentals - Home

2BR / 3BA - Sleeps 6 - Chincoteague Island Home

Josie's Dream is a newer, more modern vacation rental that is located at 4063 Grand Bay Court. This...

$65 - $108 / nt

Chincoteague Island Virginia Vacation Rentals - Home

4BR / 3BA - Sleeps 10 - Chincoteague Island Home

5216 Pine Tree Way, Oyster Bay II Rest and relax at the charming Carriage House while enjoying all of...

$143 - $228 / nt

Chincoteague Island Virginia Vacation Rentals - Apartment

3BR / 2BA - Sleeps 6 - Chincoteague Island Apartment

6321 Captain's Lane #309 When Only The Best Will Do! Located On The Edge Of Beautiful Chincoteague Bay,...

$140 - $243 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Chincoteague Island Home

7235 Bunting Very nice mobile home in private setting with large enclosed porch overlooking the marsh....

$130 - $190 / nt

Chincoteague Island Virginia Vacation Rentals - Home

2BR / 1BA - Sleeps 6 - Chincoteague Island Home

6389 Circle Drive Comfortable Island home packed with amenities. Sea Pines offers a nice treed yard and...

$105 - $125 / nt

Chincoteague Island Virginia Vacation Rentals - Home

1BR / 1BA - Sleeps 4 - Chincoteague Island Home

4150 Grumpy's Lane Charming cottage located on a quiet, private lane. Close to town. Spacious sunroom...

$80 - $110 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 3BA - Sleeps 10 - Chincoteague Island Home

5104 Blake Point Road Goose Bay tucked away off the northern end of Main Street offers a tranquil and...

$305 - $385 / nt

Chincoteague Island Virginia Vacation Rentals - Home

5BR / 2BA - Sleeps 10 - Chincoteague Island Home

3849 Main Street Charming and spacious island home offering a first floor bedroom and Outside Shower....

$180 - $240 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 9 - Chincoteague Island Home

6305 Poplar Street This sophisticated artist retreat is open and bright! Large shaded patio with comfortable...

$180 - $220 / nt

Chincoteague Island Virginia Vacation Rentals - Home

2BR / 2BA - Sleeps 8 - Chincoteague Island Home

5159 Deep Hole Road This charming island cottage built in 1920 features wood plank floors, open- beam...

$125 - $159 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Chincoteague Island Home

3241 Mulberry Lane Immaculate waterview home with super large screen porch. It has a great kitchen for...

$130 - $180 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Chincoteague Island Home

5303 Meadow Drive Well appointed rancher in Piney Island, with large screened porch and private den...

$140 - $190 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Chincoteague Island Home

6404 Pine Drive- Piney Island Brand new home in Piney Island! Ready for this summer. You'll love relaxing...

$210 - $310 / nt

Chincoteague Island Virginia Vacation Rentals - Apartment

3BR / 2BA - Sleeps 8 - Chincoteague Island Apartment

6321 Captain's Lane Unit #207 Sunset Bay Villas Classic and spacious 3 bedroom waterfront condo overlooks...

$240 - $335 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Chincoteague Island Home

3196 Main Street Enjoy sunsets from this lovely waterfront home with dock! ! Offers wireless internet...

$140 - $200 / nt

Chincoteague Island Virginia Vacation Rentals - Home

4BR / 1BA - Sleeps 8 - Chincoteague Island Home

4264 Pine Street Tucked away home close to town with large screened porch. 1BR down and sleeping porch...

$99 - $140 / nt

Chincoteague Island Virginia Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Chincoteague Island Home

5352 Sunrise Shore Drive- Oyster Bay I Waterfront 4 BR canal home in private community of Oyster Bay...

$275 - $370 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Chincoteague Island Home

6313 Cleveland Street Walk to everything including shopping, restaurants and entertainment from this...

$150 - $230 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Chincoteague Island Home

6301 Circle Drive Charming pet friendly cottage in serene island setting with easy access to the Beach...

$110 - $125 / nt

Chincoteague Island Virginia Vacation Rentals - Apartment

2BR / 1BA - Sleeps 6 - Chincoteague Island Apartment

Unit #13 Sea Tag Condominiums - 7482 East Side Drive This is the perfect spot for the fishermen in your...

$120 - $150 / nt

Chincoteague Island Virginia Vacation Rentals - Home

2BR / 1BA - Sleeps 6 - Chincoteague Island Home

3159 Bertie Street Lovely home tucked away off of South Main Street offers quiet and waterview of the...

$140 - $147 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Chincoteague Island Home

7071 Bond Street Tastefully decorated townhouse with many new appliances, screen porch and convenient...

$100 - $135 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Chincoteague Island Home

5341 Cedar Drive This ranch style home offers easy living at the beach! The bridge to Assateague Island...

$145 - $160 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Chincoteague Island Home

5497 Hibiscus Drive- Oyster Bay I Lovely home with all amenities including wireless internet. It is located...

$145 - $200 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Chincoteague Island Home

6368 Pine Drive- Piney Island Brand new Piney Island home. Spacious design open and bright with large...

$160 - $280 / nt

Chincoteague Island Virginia Vacation Rentals - Home

3BR / 3BA - Sleeps 6 - Chincoteague Island Home

7150 Silver Sails Landing Exquisite duplex offers top level comfort with screened porch and open deck...

$195 - $260 / nt

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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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