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Eastern Shore of Virginia Vacation Rentals

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Vacation Rentals in Eastern Shore of Virginia

Exterior
Key West Cottages

Key West Cottages

3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (484)
"We love Key West Cottages!"
United States
Jonathan
$94 nightly
The price is $105
Dec 3 - Dec 4
Total with taxes and fees
Key West Cottages
Exterior
Blufin Bungalows & Marina

Blufin Bungalows & Marina

3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (207)
"yesss amazing stay "
United States
EDA
Blufin Bungalows & Marina
Smart TV
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

Onancock
9.6 out of 10, Exceptional, (5)
"Nice little cottage for short stay and great location "
United States
Ronald L.
$171 nightly
The price is $189
Dec 8 - Dec 9
Total with taxes and fees
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore
Fridge, microwave, oven, stovetop
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

2.0 star property
Deep Hole
10.0 out of 10, Exceptional, (7)
"Great stay. Great host. Very clean place. Couldn’t of asked for a better host and house ! "
United States
James E.
$293 nightly
The price is $329
Dec 19 - Dec 20
Total with taxes and fees
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
Exterior detail
Timeless Elegance with Modern Luxury: Historic 6-BR Home plus attached 1-BR Apt

Timeless Elegance with Modern Luxury: Historic 6-BR Home plus attached 1-BR Apt

2.0 star property
Onancock
10.0 out of 10, Exceptional, (2)
"If you love historic old houses with grand high ceilings, you will love this Onancock house. Great for large families. Nice big kitchen with kitchenware to make meals. The one bedroom apartment is an added bonus for your family members who want more privacy. We had a fabulous time and everything was seamless from booking, to stay, to checking out. Thank you for a great family weekend!"
United States
Linda C.
$913 nightly
The price is $1,007
Dec 8 - Dec 9
Total with taxes and fees
Timeless Elegance with Modern Luxury: Historic 6-BR Home plus attached 1-BR Apt
Beach
Experience Tiny Living, in Cape Charles, Va

Experience Tiny Living, in Cape Charles, Va

Cape Charles
10.0 out of 10, Exceptional, (1)
"Exactly what listing said! Was super clean and perfect for our short trip! Easy drive to and from the beach and the town of Cape Charles"
United States
Ella D.
$253 nightly
The price is $283
Dec 3 - Dec 4
Total with taxes and fees
Experience Tiny Living, in Cape Charles, Va
Terrace/patio
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, (22)
"Loved that it was right on the bay. "
United States
Debra
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Beach
Tiny House close to the Beaches of Cape Charles

Tiny House close to the Beaches of Cape Charles

Cape Charles
10.0 out of 10, Exceptional, (1)
"I enjoyed staying here, solid place!"
United States
Charles B.
$286 nightly
The price is $320
Dec 3 - Dec 4
Total with taxes and fees
Tiny House close to the Beaches of Cape Charles
Beach nearby
Hippie Hideaway - Tiny House w/ Fire Pit & BBQ

Hippie Hideaway - Tiny House w/ Fire Pit & BBQ

Cape Charles
10.0 out of 10, Exceptional, (1)
"This was a great stay, we loved everything about it. Highly recommended. We will definitely return."
United States
William
$260 nightly
The price is $291
Dec 3 - Dec 4
Total with taxes and fees
Hippie Hideaway - Tiny House w/ Fire Pit & BBQ
Beach nearby
Whimsical Tiny House, Cape Charles Virginia

Whimsical Tiny House, Cape Charles Virginia

Cape Charles
9.2 out of 10, Wonderful, (14)
"The place was cute and clean, it is NOT in the town of Cape Charles. Surrounding area less than desirable. Perfect if the actual tiny house was within the town as advertised. "
United States
Tanya R.
$291 nightly
The price is $325
Jan 2 - Jan 3, 2026
Total with taxes and fees
Whimsical Tiny House, Cape Charles Virginia
Property grounds
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, (59)
"Nick is an excellent host. The home was so fun for our family to stay in. The view is so beautiful and peaceful. It is even more beautiful in person. Short drive to reach Chincoteague and Assateague. Stocked with everything you need. I walked down the street and got a massage using the info provided in the house. Thanks for a wonderful and beautiful stay. "
United States
Natalie K.
$374 nightly
The price is $413
Dec 4 - Dec 5
Total with taxes and fees
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities
Beach nearby
Pet Friendly Tiny Livin 3min from Cape Charles

Pet Friendly Tiny Livin 3min from Cape Charles

Cape Charles
10.0 out of 10, Exceptional, (11)
"Great stay easy access to Cape Charles and the beach"
United States
andrew c.
$337 nightly
The price is $377
Dec 3 - Dec 4
Total with taxes and fees
Pet Friendly Tiny Livin 3min from Cape Charles
1 bedroom, iron/ironing board, WiFi, bed sheets
Tiny House Hideaway with King sized Bed

Tiny House Hideaway with King sized Bed

Cape Charles
9.6 out of 10, Exceptional, (5)
"We absolutely enjoyed our little tiny home! The property was great and the things to do close by were great! We would definitely stay again! "
United States
Leslie
$286 nightly
The price is $320
Dec 3 - Dec 4
Total with taxes and fees
Tiny House Hideaway with King sized Bed
Interior
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

Up the Neck
9.4 out of 10, Exceptional, (137)
"Nice and quiet spot on island, kind of away from the busy parts of island. "
United States
Derek W.
$327 nightly
The price is $356
Dec 10 - Dec 11
Total with taxes and fees
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Golf
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)
"We thoroughly enjoyed our stay. Beautiful home in an excellent location. Close to everything. We would definitely stay again. "
United States
Beverly D.
$509 nightly
The price is $575
Dec 3 - Dec 4
Total with taxes and fees
Bay Creek Meets Historic Cape Charles! pool access!
Marina
The Captains Quarters located in Cape Charles, VA offers breathtaking views.

The Captains Quarters located in Cape Charles, VA offers breathtaking views.

Cape Charles
9.6 out of 10, Exceptional, (40)
"We were in town for a wedding and booked The Captains Quarters. We had a great stay and enjoyed the location - so fun to watch the boats come in and just a short walk into town. The place was clean and comfortable and the hosts were great. Thanks for sharing your place with us!"
United States
Alyssa H.
$315 nightly
The price is $358
Dec 4 - Dec 5
Total with taxes and fees
The Captains Quarters located in Cape Charles, VA offers breathtaking views.
Beach nearby
Restored 1930’s Tiny Home 3 min to Cape Charles

Restored 1930’s Tiny Home 3 min to Cape Charles

Cape Charles
$260 nightly
The price is $291
Dec 3 - Dec 4
Total with taxes and fees
Restored 1930’s Tiny Home 3 min to Cape Charles
Beach nearby, sun loungers, beach towels
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, (26)
"Our family loved the house, location, and the wonderful town of Cape Charles. We will be coming back next year. "
United States
Todd E.
$862 nightly
The price is $972
Dec 3 - Dec 4
Total with taxes and fees
The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach
Beach nearby, sun loungers, beach towels
Golf cart included! 5 blocks to the beach, and in historic district!

Golf cart included! 5 blocks to the beach, and in historic district!

Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (15)
"A warm, inviting house with everything you need. Private backyard. Joel and Brittney are super responsive hosts who will make sure you have a nice stay!"
United States
Donna A.
Golf cart included! 5 blocks to the beach, and in historic district!
TV, offices
Bayside Getaways Oyster Oasis - Chesapeake Properties

Bayside Getaways Oyster Oasis - Chesapeake Properties

Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (3)
"Clean, nicely decorated, comfortable bed, and excellent location. "
United States
Alice T.
$447 nightly
The price is $506
Dec 3 - Dec 4
Total with taxes and fees
Bayside Getaways Oyster Oasis - Chesapeake Properties
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

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

10/10 Excellent
"Nice, reasonably priced "
Bhaskar 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

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 $105 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

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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.

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