Holiday Rentals in Eastern Shore of Virginia

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Our top choices for Eastern Shore of Virginia holiday rentals

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (507 reviews)
"Love the resort! "
United States
Hannah
Key West Cottages

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (209 reviews)
"yesss amazing stay "
United States
EDA
Blufin Bungalows & Marina

Cozy cottage w/creekside fire pit & pet‑friendly

Cozy cottage w/creekside fire pit & pet‑friendly
Up the Neck
9.4 out of 10, Exceptional, (137 reviews)
"House was exactly as advertised. Everything worked as expected. This house is one of the few in this town that offered linens, a big selling point for us."
United States
Kato A.
The price is €249
includes taxes & fees
8 Feb - 9 Feb
Cozy cottage w/creekside fire pit & pet‑friendly

Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities
Captain's Cove
9.8 out of 10, Exceptional, (61 reviews)
"This is a unique home with beautiful views! The amenities were wonderful, the home was so clean, and Nick was great with checking in to make sure everything was good. Would definitely stay here again! "
United States
Kristy C.
The price is €374
includes taxes & fees
8 Feb - 9 Feb
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Salt Box, One Block to the Beach

Salt Box, One Block to the Beach
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (18 reviews)
"Two blocks to Mason Ave and two blocks to the beach, the location was a real highlight for us. The house was clean, and check-in/check-out could not be easier. I was a little nervous about having the owners right next-door, but they were so polite when we saw them, and that was very rare. We had a great time, and hope that it’s available for our Cape Charles trip next year. "
United States
David S.
The price is €259
includes taxes & fees
22 Feb - 23 Feb
Salt Box, One Block to the Beach

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

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Down the Marsh
9.8 out of 10, Exceptional, (25 reviews)
"Loved that it was right on the bay. "
United States
Debra
The price is €136
includes taxes & fees
12 Feb - 13 Feb
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Assateague Inn 104 by Seaside Vacations & Sales

Assateague Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (22 reviews)
"Stay at Assateague Inn was clean, comfy, cozy, and convenient. "
United States
Anonymous traveller
The price is €165
includes taxes & fees
8 Feb - 9 Feb
Assateague Inn 104 by Seaside Vacations & Sales

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
9.2 out of 10, Wonderful, (31 reviews)
"Everything was great. Will stay again "
United States
Richard R.
The price is €164
includes taxes & fees
9 Feb - 10 Feb
Only 5 min. from the Beach!

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

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Downtown Chincoteague
10.0 out of 10, Exceptional, (66 reviews)
"Everything was just perfect! Enjoyed our three day stay! "
United States
Mary C.
The price is €249
includes taxes & fees
7 Feb - 8 Feb
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Renovated Gem: Walk to Beach, Historic District Shops, Restaurants, Central Park

Renovated Gem: Walk to Beach, Historic District Shops, Restaurants, Central Park
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (82 reviews)
"Beautiful home and very well equipped with everything you would need to have a wonderful vacation. Perfect location just blocks from the park/play ground, down town and the beach."
United States
Scott D.
The price is €1,233
includes taxes & fees
8 Feb - 9 Feb
Renovated Gem: Walk to Beach, Historic District Shops, Restaurants, Central Park

Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
Accomac
10.0 out of 10, Exceptional, (26 reviews)
"Beautiful, comfortable, and quiet. Everything we needed and more!!Very helpful and friendly hosts. "
United States
Karen K.
The price is €268
includes taxes & fees
7 Feb - 8 Feb
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Maryland - Brand new condo in Downtown Cape Charles!

Maryland - Brand new condo in Downtown Cape Charles!
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (1 review)
"Clean, great amenities, and perfect location. Owners were nearby and friendly and helpful"
United States
Meghan D.
The price is €633
includes taxes & fees
20 Feb - 21 Feb
Maryland - Brand new condo in Downtown Cape Charles!

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

Bay cottage, Beach 100 yards away! RESERVE NOW!!!
Historic Downtown Cape Charles
9.6 out of 10, Exceptional, (145 reviews)
"Nicely located. Clean. Convenient to town center and beach. Good on-street parking and renter/owner communication. Limited household amenities. Could use an interior refresh and bathroom updating. "
United States
Thomas R.
The price is €406
includes taxes & fees
7 Feb - 8 Feb
Bay cottage, Beach 100 yards away! RESERVE NOW!!!

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.2 out of 10, Wonderful, (54 reviews)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is €377
includes taxes & fees
7 Feb - 8 Feb
The purple door at the bay.

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
9.4 out of 10, Exceptional, (8 reviews)
"Close to everything, quiet, clean"
United States
Eileen D.
The price is €186
includes taxes & fees
8 Feb - 9 Feb
Only 5 min. from the Beach!

Bay Creek Meets Historic Cape Charles! pool access!

Bay Creek Meets Historic Cape Charles! pool access!
Cape Charles
10.0 out of 10, Exceptional, (31 reviews)
"We had a great stay. The house was perfect for a family with young children and well-equipped for our family. "
United States
Sarah M.
The price is €419
includes taxes & fees
8 Feb - 9 Feb
Bay Creek Meets Historic Cape Charles! pool access!

Indoor-Outdoor 2BR on Working Farm | Creek View

Indoor-Outdoor 2BR on Working Farm | Creek View
Melfa
The price is €243
includes taxes & fees
10 Feb - 11 Feb
Indoor-Outdoor 2BR on Working Farm | Creek View

Blue Haven - Chesapeake Properties

Blue Haven - Chesapeake Properties
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (3 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved pretty much everything about this house! Highly recommend!"
United States
Elizabeth K.
The price is €619
includes taxes & fees
28 Feb - 1 Mar
Blue Haven - Chesapeake Properties

Coral Villa

Coral Villa
Piney Island
8.4 out of 10, Very good, (5 reviews)
"Close to the beach. Peaceful stay. My family enjoyed."
United States
Natasha M.
The price is €168
includes taxes & fees
17 Feb - 18 Feb
Coral Villa

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

The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach
Cape Charles
10.0 out of 10, Exceptional, (28 reviews)
"The comfort and ease of this property was perfect for our quick wedding weekend! I just wish we could have more time to relax and use the amenities."
United States
Barbara A.
The price is €819
includes taxes & fees
7 Feb - 8 Feb
The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach
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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Top Eastern Shore of Virginia Hotel Reviews

Find out more about Eastern Shore of Virginia

Everything you need to know about Eastern Shore of Virginia holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Eastern Shore of Virginia holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Eastern Shore of Virginia holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Eastern Shore of Virginia holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Eastern Shore of Virginia. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Eastern Shore of Virginia holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Eastern Shore of Virginia holiday rentals we have selected for you start as low as €136 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Eastern Shore of Virginia rentals

At Expedia, we put the best Eastern Shore of Virginia holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Eastern Shore of Virginia rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Eastern Shore of Virginia holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Eastern Shore of Virginia. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.