Photo by Got The Travel Bug Too

Eastern Shore of Virginia Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Eastern Shore of Virginia vacation rentals

Exterior
Key West Cottages

Cottage in Downtown Chincoteague

3.0 star property
9.8 out of 10, Exceptional, (487)
"We love Key West Cottages!"
United States
Jonathan
$119 nightly
The price is $134
Dec 21 - Dec 22
Total with taxes and fees
Key West Cottages
Exterior
Blufin Bungalows & Marina

Vacation Home in Down the Marsh

3.0 star property
9.6 out of 10, Exceptional, (207)
"yesss amazing stay "
United States
EDA
$99 nightly
The price is $111
Dec 11 - Dec 12
Total with taxes and fees
Blufin Bungalows & Marina
Pool
1BR Waterfront cottage with a view of the wild Chincoteague ponies!

Cottage in Dodge City

9.6 out of 10, Exceptional, (14)
"Wonderful hosts at a beautiful property. The cottage was quaint, safe and clean, just as advertised, and was perfect for a 2 day quiet get away. The overall property is well cared for and provides for a warm sense of community for the guests. "
United States
Carol P.
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Fridge, microwave, oven, stovetop
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Vacation Home in Downtown Chincoteague

10.0 out of 10, Exceptional, (65)
"Great location. The house was perfect for our family. I especially enjoyed the swing on the porch "
United States
pat B.
$221 nightly
The price is $248
Dec 10 - Dec 11
Total with taxes and fees
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Beach
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Cottage in Dodge City

9.6 out of 10, Exceptional, (52)
"Wonderful property. Very clean, comfortable and has a great view. Awsom host. "
United States
Janet L.
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Smart TV
Perfect Cozy Vacation Rental on the Eastern Shore

Condo in Cape Charles

8.2 out of 10, Very Good, (28)
"From the outside the place looked kind of bare and not very outstanding. However, the inside was fine. Co.fortable bed and nice accommodations. "
United States
Cheryl T.
Perfect Cozy Vacation Rental on the Eastern Shore
Outdoor dining
Driftwood- Firepit, Bikes, Closest Neighborhood to Assateague Beach

Vacation Home in Piney Island

Driftwood- Firepit, Bikes, Closest Neighborhood to Assateague Beach
Outdoor spa tub
Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

Vacation Home in Picketts Harbor

10.0 out of 10, Exceptional, (65)
"Just like it was represented on VRBO! Excellent property, rooms were great with plenty of space. The furnishings were complete and in working order. Every detail was thought of - even a firepit that was prepared to light! "
United States
Mark B.
Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway
Interior
At the Water's Edge - is there anywhere you'd rather be?!

Vacation Home in Chincoteague Island

10.0 out of 10, Exceptional, (53)
"My son, daughter in law and other family members "
United States
Margie O.
At the Water's Edge - is there anywhere you'd rather be?!
Fridge, microwave, oven, stovetop
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

Cottage in Downtown Chincoteague

10.0 out of 10, Exceptional, (19)
"Great host and the house was exactly as described. It provided what we needed for our stay."
United States
Janna M.
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
Microwave, oven, stovetop, coffee/tea maker
Assateague Inn 111 by Seaside Vacations & Sales

Condo in Chincoteague Island

8.2 out of 10, Very Good, (32)
"It was all we needed. No frills, but in a great location and the pool was wonderful. "
United States
jennifer g.
$183 nightly
The price is $191
Dec 11 - Dec 12
Total with taxes and fees
Assateague Inn 111 by Seaside Vacations & Sales
Terrace/patio
The purple door at the bay.

Vacation Home in Captain's Cove

9.2 out of 10, Wonderful, (54)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
$409 nightly
The price is $451
Dec 10 - Dec 11
Total with taxes and fees
The purple door at the bay.
Outdoor pool
Nassawadox Creek Waterfront Home with Private Pool

Vacation Home in Exmore

10.0 out of 10, Exceptional, (61)
"A wonderful and relaxing stay. The house was well equipped and had everything we needed. The pool area was great and we enjoyed it daily, along with grilling and the fire pit. The perfect escape for this city family! "
United States
Vanda T.
Nassawadox Creek Waterfront Home with Private Pool
Outdoor dining
Island Retreat by Seaside Vacations & Sales

Vacation Home in Chincoteague Island

9.0 out of 10, Wonderful, (16)
"Quiet place with everything we needed to be comfortable for our 10th anniversary. We loved it & are looking forward to a return trip."
United States
Anita A.
Island Retreat by Seaside Vacations & Sales
Exterior
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Vacation Home in Birch Town

9.6 out of 10, Exceptional, (42)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
$358 nightly
The price is $402
Dec 10 - Dec 11
Total with taxes and fees
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Terrace/patio
Assateague Inn 104 by Seaside Vacations & Sales

Condo in Chincoteague Island

9.6 out of 10, Exceptional, (22)
"Stay at Assateague Inn was clean, comfy, cozy, and convenient. "
United States
Anonymous traveler
$183 nightly
The price is $191
Dec 11 - Dec 12
Total with taxes and fees
Assateague Inn 104 by Seaside Vacations & Sales
Fridge, microwave, oven, stovetop
The Blue Crab - Your Dream Vacation awaits you!

Vacation Home in Deep Hole

2.0 star property
9.8 out of 10, Exceptional, (14)
"The Blue Crab was perfect for our family vacation. It was beautiful, clean, spacious, and had everything we needed to enjoy our stay. If we come back, we’ll be staying at The Blue Crab again! "
United States
Erin P.
The Blue Crab - Your Dream Vacation awaits you!
Interior
Cabin at Holdens Creek on Eastern Shore of VA

Cabin in Temperanceville

9.6 out of 10, Exceptional, (180)
"We had a wonderful stay!"
United States
Anna-Marie
Cabin at Holdens Creek on Eastern Shore of VA
Property grounds
Sunrise - Waterfront home ,lg back waterfront deck. NO LINENS

Vacation Home in Chincoteague

8.0 out of 10, Very Good, (23)
"Really great location to enjoy the sunrise!"
United States
Leandra
Sunrise - Waterfront home ,lg back waterfront deck. NO LINENS
Exterior detail
Bay cottage, Beach 100 yards away! RESERVE NOW!!!

Vacation Home in Historic Downtown Cape Charles

9.6 out of 10, Exceptional, (145)
"Had a wonderful time , house was warm and inviting walking distance to both the beach and local shops and restaurants. Hope we ca n come back again@"
United States
Jean w.
$423 nightly
The price is $479
Jan 2 - Jan 3, 2026
Total with taxes and fees
Bay cottage, Beach 100 yards away! RESERVE NOW!!!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Eastern Shore of Virginia Hotel Reviews

Key West Cottages

Key West Cottages

10/10 Excellent
"The friendliest staff and gorgeous rooms "
Donna 2-night trip
Posted 2 days ago
Key West Cottages

Find out more about Eastern Shore of Virginia

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

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Eastern Shore of Virginia vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Eastern Shore of Virginia vacation 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 low season months. For more hustle and bustle, you may prefer to visit Eastern Shore of Virginia in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $111 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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.

Explore a world of travel with Expedia