Holiday Homes in Eastern Shore of Virginia

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Featured Holiday Homes in Eastern Shore of Virginia

Blufin Bungalows & Marina

3.0 star property
9.4 out of 10, Exceptional, (85)
"Great stay! Our family had a great time!"
Blufin Bungalows & Marina

The Brass Crab - Check in/out any day!

10.0 out of 10, Exceptional, (144)
"Nice property with lots of space."
The Brass Crab - Check in/out any day!

Doublemint | Chesapeake Properties

10.0 out of 10, Exceptional, (40)
"My best friend and I took our daughters (ages 4, 7, and 8) to Cape Charles for vacation. This was the perfect place to stay! We are already planning to take a trip back there!!"
Doublemint | Chesapeake Properties

BEACHFRONT COTTAGE JUST STEPS AWAY FROM BEACH!

9.4 out of 10, Exceptional, (34)
"We loved Cape Charles for it's laded back environment. House was a 1960's property but it had everything you need and more."
BEACHFRONT COTTAGE JUST STEPS AWAY FROM BEACH!

The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach

10.0 out of 10, Exceptional, (13)
"The home was clean and exactly as described. Richard was quick to respond and we enjoyed our stay!"
The price is AU$1,578
includes taxes & fees
19 Feb - 20 Feb
The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach

Oyster Shack - true gem in heart of downtown!

2.0 star property
Oyster Shack - true gem in heart of downtown!

Bay cottage, Beach 100 yards away! RESERVE NOW!!!

9.6 out of 10, Exceptional, (130)
"What a treasure!!! The weather was cold and we even had snow! We stayed really warm lots of good food and sightseeing. We will definitely be back!"
The price is AU$739
includes taxes & fees
20 Feb - 21 Feb
Bay cottage, Beach 100 yards away! RESERVE NOW!!!

The purple door at the bay.

9.4 out of 10, Exceptional, (40)
"We loved the view and can not wait to go back!"
The price is AU$749
includes taxes & fees
19 Feb - 20 Feb
The purple door at the bay.

Key Lime Cottage: Your Cape Charles Beachside Retreat

10.0 out of 10, Exceptional, (37)
"Great place to stay. Very clean and perfect size for three to four couples "
Key Lime Cottage: Your Cape Charles Beachside Retreat

Family Rental, Best location to Central Park and beach!

10.0 out of 10, Exceptional, (26)
"Great "
Family Rental, Best location to Central Park and beach!

Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach

10.0 out of 10, Exceptional, (20)
"This house is nicely decorated and well appointed. The kitchen is fully furnished with all the necessary equipment and plate ware. The furniture is comfortable and high quality. The garages are also equipped with beach equipment, games, and an excellent golf cart (extra fee for use)."
Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach

Classically Current | Chesapeake Properties

9.8 out of 10, Exceptional, (84)
"We have booked this property now three times for our large family and it's perfect for us everytime! Will book again next year."
Classically Current | Chesapeake Properties

🍑 The Peach St. House - 1 Block to Park and Shops, close to beach!

9.8 out of 10, Exceptional, (9)
"This beautiful was in the perfect location in Cape Charles. 10/10"
The price is AU$835
includes taxes & fees
22 Feb - 23 Feb
🍑 The Peach St. House - 1 Block to Park and Shops, close to beach!

Just One House From The Beach Barefoot Bungalow Offers A Sweet Beach Vacation

10.0 out of 10, Exceptional, (41)
"Our family greatly enjoyed staying here. Easy process. The Property is well-maintained and has a great deal of amenities that we utilized. Would absolutely stay here again!"
Just One House From The Beach Barefoot Bungalow Offers A Sweet Beach Vacation

HGTV House! 2 Blocks to Beach- 2024 New Bathroom!

3.0 star property
10.0 out of 10, Exceptional, (14)
"This lovely home is a great combination of historic character and modern convenience. Everything was within easy walking distance. Chris was a wonderful host!"
HGTV House! 2 Blocks to Beach- 2024 New Bathroom!

Trembling Bay - Waterfront; Private pier!

8.8 out of 10, Excellent, (39)
"It was the perfect fit for me and my hubby. He is on crutch's due to a botch hip surgery many yrs ago... anyway the house 1st floor is very handicap friendly. The master bedroom bed was comfy but very low to the ground. And bring your own pillows. Not many there. The one thing we were really looking forward to was going out on the dock, but I think between the storm that had come and just wear and tear on the wooden pathway to the dock, it fell down. We were not able to get out to the water. We...
Trembling Bay - Waterfront; Private pier!

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

10.0 out of 10, Exceptional, (4)
"We had a great time and stay at this property!! Would love to stay here again!"
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

Newly renovated home just steps from the beach!

10.0 out of 10, Exceptional, (49)
"This was our second stay at Sandcastle. Great location and place to stay! Missed some amenities like a TV in bedrooms at night and a simple hair dryer. Could not have been much better though all and all! great stay"
Newly renovated home just steps from the beach!

Chincoteague Island Creekside Cottage

9.4 out of 10, Exceptional, (3)
"House was very clean and beautiful kitchen well laid out with everything you need for cooking etc. Plenty of room for everyone here. Only thing missing is outside shower. "
Chincoteague Island Creekside Cottage

Saltwater Pony on Chincoteague Island!

9.6 out of 10, Exceptional, (5)
"Nice quiet stay"
Saltwater Pony on Chincoteague Island!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Eastern Shore of Virginia

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (325)
"Very nice cottages "
The price is AU$213
includes taxes & fees
4 Mar - 5 Mar
Key West Cottages

Blufin Bungalows & Marina

3.0 star property
9.4 out of 10, Exceptional, (85)
"Great stay! Our family had a great time!"
Blufin Bungalows & Marina

Cozy Little Cottage on chincoteague island va.

9.4 out of 10, Exceptional, (36)
"The cottage is as described. There is no stove but it truly didn’t matter. Bed is very compfy. Shower is clean and hot. Quit neighborhood. The screened in porch is the best! Coffee and reading in the rockers. The cottage is close to everything !Thank you Don. We loved our stay."
Cozy Little Cottage on chincoteague island va.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.