Skip to content

Eastern Shore of Virginia vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Eastern Shore of Virginia

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Hotel room in Cape Charles
The Laughing King Retreat, Honeymoon Island Suite
The Laughing King Retreat is an adults only, organic waterfront farm situated directly on the peaceful waters of the Chesapeake Bay. Your private guest suite will enjoy breathtaking sunrises and sunsets, private waterfront pool, private beach, hiking trails, miles of soft sugar sand sandbars to explore and enjoy. Private Chesapeake Bay water access for boating, swimming, paddle boarding, fishing or just soaking. For a complete list of all the retreat rooms click the photo of me and Suzanne.
$170 per night
Cottage in Hacksneck
Pretty Byrd Cottage, a Victorian Bayfront Getaway!
Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and balconies that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!
$290 per night
Guesthouse in Onancock
Crews Quarters - Eastern Shore Retreat!
Crews Quarters is located on the edge of Deep Creek with upper & lower decks where you can enjoy the water front panoramic view of the inner Chesapeake Bay. Property has a community dock and fire pit. Enjoy historic Onancock and its many restaurants, galleries, antique shops, museums and live theatre. Try any of the 27 day trip adventures on the Delmarva - Assateague Island National Park to see the wild horses or beach activities, ferry to Tangier Island for fresh local crab cakes, and more!
$120 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Eastern Shore of Virginia waterfront vacation rentals

Home in Onancock
Charming Waterfront Cottage on Cedar Creek
$132 per night
Guest suite in Chincoteague
Baywatch Upper-Waterfront & Roaming Ponies!
$40 per night
Home in Chincoteague
The Honeymooner-Deep Water Dock Chincoteague Bay
$228 per night
Tiny home in Cape Charles
Smith Beach. Unique, luxurious creekside stay
$149 per night
Place to stay in Machipongo
Smokehouse on the Chesapeake Bay
$120 per night
Cottage in Exmore
Silver Beach: Sunset Bay Cottage on Private Beach
$225 per night
Home in Onancock
NEW - A “True” Chesapeake Bay Waterfront Escape!
$355 per night
Cottage in Chincoteague
Shackeau East - Stunning Bay Views from this delightful Waterfront Cottage!
$105 per night
Home in Franktown
Large Waterfront House: Eastern Shore of Virginia
$395 per night
Home in Chincoteague Island
Tranquil Shores - Nature Inspired Relaxation!
$107 per night
Cottage in Exmore
Cozy Waterfront Escape Where Pets Stay For Free!
$200 per night
Cottage in Chincoteague Island
★ Jay’s Waterfront Retreat: Private Dock- Kayaks-Fire Pit-Bikes-Beach-Pet Friendly ★
$97 per night