Holiday Homes in Eastern Shore of Virginia

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Eastern Shore of Virginia and around

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (163)
"excellent place to stay on the water"
Blufin Bungalows & Marina

Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex

9.8 out of 10, Exceptional, (89)
"This is a nice quiet location but still close to the park and the restaurants and shops. We enjoyed our stay here."
Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex

Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.

10.0 out of 10, Exceptional, (142)
"Perfect cozy place to stay at the end of a quiet pine tree lined street with easy access to the national park and all it offers."
Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.

Pet Friendly Tiny Livin 3min from Cape Charles

10.0 out of 10, Exceptional, (8)
"We booked this tiny house for a spontaneous night away to do some fishing in Cape Charles. The property and house were absolutely adorable and the accommodations were exactly what we needed for a weekend away. The property had an amazing bonfire pit and grill if you don’t want to eat out, and there’s plenty of space with a fence and grassy areas if you’re traveling with a dog. The owners were extremely communicative and even went to the trouble of mailing us back something we left. We would...
The price is €241
includes taxes & fees
1 Sept - 2 Sept
Pet Friendly Tiny Livin 3min from Cape Charles

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

9.6 out of 10, Exceptional, (15)
"We stayed three nights and they were all delightful. The cabins are super clean, well equipped, comfortable beds, screened in front porch.- in other words anything you could wish! My only critique is that I don’t think the smoke alarm in the CO2 detectors were listed in the ad and they should be because they definitely are there!We will gladly come again someday."
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

The Sandpiper has gone SOLAR!!! exceptional family vacation, and private pool.

10.0 out of 10, Exceptional, (29)
"Great place to stay was the best equipped place i have ever rented the owner takes care of their customers. Great stay"
The Sandpiper has gone SOLAR!!! exceptional family vacation, and private pool.

A Perfect Location Next to Park and Walkable to Town and Beach. Pet Friendly!

9.6 out of 10, Exceptional, (11)
"Great play to stay with your family! Close to the park and town, and an easy golf cart ride to the beach!"
A Perfect Location Next to Park and Walkable to Town and Beach. Pet Friendly!

Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

10.0 out of 10, Exceptional, (60)
"Wanted a private place on the water, pictures don’t show a new home built directly behind this house. The fire pit and hot tub are basically in the front yard of the new house. If privacy aren’t an issue and great views are all the matters then this place is perfect."
Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

Seas the Moment - Bay, Channel, AND OCEAN VIEWS!

10.0 out of 10, Exceptional, (1)
"Will reserve this house many time is possible. Great location, new house and great comfort. Amazing place "
Seas the Moment - Bay, Channel, AND OCEAN VIEWS!

Gorgeous New 5 BDR, 4 BA Beach Home With Tower Outlook Suite!

9.8 out of 10, Exceptional, (11)
"We loved our recent stay in Cape Charles. The house is a great location to the beach and only minutes into town. We will definitely come back!"
Gorgeous New 5 BDR, 4 BA Beach Home With Tower Outlook Suite!

Deja Blue on Chincoteague Island

9.2 out of 10, Wonderful, (7)
"Great communications and great little get away"
Deja Blue on Chincoteague Island

Cattail Cottage -Allergy Friendly Home -In Town-LINENS & TOWELS PROVIDED

9.6 out of 10, Exceptional, (32)
"This charming, coastal themed cottage was conveniently located to Assateague Island, Wallops Island, and Chincoteague! It was clean, gave abundant information on the area, and in a quiet location. My husband and I enjoyed our stay at our home away from home for a reasonable price!"
Cattail Cottage -Allergy Friendly Home -In Town-LINENS & TOWELS PROVIDED

Newly renovated home just steps from the beach!

10.0 out of 10, Exceptional, (55)
"The property was perfect for our group of three couples. Our family had a great time being so close to the beach and 'into town'. A great place to stay and will stay here again when we come back to Cape Charles. "
Newly renovated home just steps from the beach!

Gorgeous 5 Bedroom, 3 Bath Waterfront Home!

10.0 out of 10, Exceptional, (8)
"Annual visit in Cape Charles Virginia"
Gorgeous 5 Bedroom, 3 Bath Waterfront Home!

Chesapeake Bay View

9.8 out of 10, Exceptional, (76)
"Lovely house. "
Chesapeake Bay View

Firepit/BBQ, Minutes to Beach & Park | Deja Blu II

10.0 out of 10, Exceptional, (1)
"We loved our stay here. It has everything you need to cook as well. Great to use the grill in the back and loved how easy parking was. The location couldn't be better. So close to the beach and the rest of Cape Charles!"
Firepit/BBQ, Minutes to Beach & Park | Deja Blu II

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

9.6 out of 10, Exceptional, (42)
"We enjoyed our stay at Waterside. Location was perfect and host was very responsive to questions. A great rental for a few friends and/or family."
The price is €407
includes taxes & fees
2 Sept - 3 Sept
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

10.0 out of 10, Exceptional, (54)
"An instant nervous system reset."
The price is €282
includes taxes & fees
8 Sept - 9 Sept
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

The Happy Crab - Waterfront on Chincoteague Island!

9.0 out of 10, Wonderful, (14)
"Really enjoyed the place, beautiful sunrises, great little island and food "
The Happy Crab - Waterfront on Chincoteague Island!

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (53)
"The roundhouse was amazing on many levels, figuratively and literally. There are many creature, comforts throughout this sprawling home and the views were serene and relaxing, and the couches and beds were comfy! And the host was very helpful and accommodating. Highly recommend would definitely stay here again."
The price is €534
includes taxes & fees
3 Sept - 4 Sept
Stunning waterfront panoramic view getaway house
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Eastern Shore of Virginia Hotel Reviews