
Places to stay near Smith Island Beach
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Top-rated vacation rentals near Smith Island Beach
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Quiet Neighborhood 7 Miles From the Beaches
Be sure to read about the pricing using both bedrooms below in 2nd paragraph. My house is in a quiet neighborhood by a creek of the Lynnhaven River 7 miles from the Oceanfront/Chesapeake Bay with easy access to the interstate and surrounding cities in Hampton Roads. Only minutes from Town Center and local malls. Your private area is the 1st level with your own private entrance, but no kitchen. There is small microwave and a coffee machine in the unit , & a small fridge on the screened-in-porch.

Guesthouse at Vessel Farm & Winery, Waterfront
Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

Just Steps Away to the Beach
Enjoy Oct. & Nov. at Va. Beach--average day temp. 60-70 degrees. Just steps or bike through a nice area to the beach, restaurants, culture, The Dome, Convention Ctr & other activities. Take a 10-min. walk or bike to the beach (7 short blocks). No traffic or parking hassles! We are close to I264, several military bases & Hilltop Shopping area. This is a quiet neighborhood & convenient location. Perfect for couples & solo travelers. NO animals or pets allowed! NO children under 13 yrs. of age!

The Cheriton Loft
Located in the heart of Cheriton, The Loft is a bright and sunny apartment. It is perfect for a couple and one child, three friends or one person. Cheriton is an up and coming village which is home to several galleries and an art center. It is less than 4 miles to the charming town and beach of Cape Charles, 3 miles to Oyster Boat Landing and 8 miles to Kiptopeke State Park. The apartment is owned and decorated by"The Sheep Lady", a local painter, illustrator and writer of children's books.

Private romantic pet friendly waterfront cottage
On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

Salty Willow-a “suite retreat” in the heart of VB!
We love welcoming people to our home in the heart of Virginia Beach! Come and go as you please in our guest suite with a separate entrance and privacy latches-no one will enter your space. You will also have the added convenience of having the host family on site. We do our best to provide the comforts of home. -fridge/freezer -beach essentials -toaster -coffee bar -extra essentials We want you to make yourself at home with us. Maybe we’ll enjoy a summer night together on the porch soon!

Sweet Suite!
Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

The Laughing King Retreat Honeymoon Island Cottage
Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

Fully Renovated Beach Loft Block Off OceanFront
Come enjoy everything Virginia Beach has to offer. Our newly renovated beach condo has all of the comforts of home and accommodates 2-3 adults perfectly. Bedroom has a queen size bed and common area has a futon that pulls out into a bed. Smart TVs in both rooms. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. You can walk to the beach in 3 minutes or less! Come have a relaxing and fun vacation at the beach.

Ultimate Cabin Farm Stay Cape Charles
Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

The Llama House
Located half-way between Mathews and Gloucester on the beautiful North River with views of the Mobjack Bay, New Point Comfort Lighthouse and Gloucester Point. The ideal spot for anyone needing to reconnect with someone, nature, or themselves. Enjoy fishing, crabbing, kayaking, playing corn hole, birdwatching, napping in a hammock, sipping wine, grilling out, amazing sunsets, listening to old records, playing the ukulele, and other simple pleasures of days gone by.
Popular amenities for vacation rentals near Smith Island Beach
Other top sights near Smith Island Beach
Condo rentals with wifi

Tropical 2BR Condo Getaway 1 Block from the Beach!

Best Value Condo in Downtown Norfolk

Walk to beach lovely 2/2 in "Kingsmill on James"

Spacious Captain’s Beach Suite Near Rudee Inlet

Oceanfront Gem VaB Studio Exceptional Views

Beach Bungalow on the Boardwalk

*Mid/Long Term Rental* Cozy Home at Mary Roberts

Luxury Riverfront Condo w/ sunrise & sunset views
Family-friendly house rentals

Stylishly Renovated | Golf Cart Avail. | Bakery!

Cozy Single Family Home

@Whit’s End? Come in and Relax

1891 Coastal Charmer: fully renovated farmhouse

"Live Life Sunnyside Up" - Minutes From The Beach!

Fisherman's Getaway

Waterfront Cottage Getaway Views/Kayaks/Fire Pit

Sun & fun at Sundrop
Apartment rentals with air conditioning

Close 2 East Beach, EOV, King Bed, Top Floor

The Fish House

902C Poseidon’s Cottage: Sauna & Charm By The Sea

The Cottage at Sojourn: Buckroe - one bedroom

Private apartment only 3 blocks from the Beach

Cozy 3-Bedroom Beach Bungalow Short walk to Beach

Centrally Located Sleek Studio Apartment

Cozy Ground Floor Apt in Historic Home
Other great vacation rentals near Smith Island Beach

The Ladybug - arcade, dog-friendly, firepit, & EV

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

Peaceful Haven: nature & charming town

Private Beach Access at The OV Beach House

Beachfront Exclusive Bay front Suite

"The Little Red Cabin" aka The Galley

Waterfront Guesthouse II on the Rappahannock

Walk 2 Beach & Restaurants-Central Park- King Bed!
Destinations to explore
- Chesapeake Bay
- Virginia Beach Oceanfront
- Carova Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
- Bethel Beach
- Outlook Beach
- Kiptopeke Beach
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Virginia Beach National Golf Club
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- James River Country Club
- Wilkins Beach
- Little Creek Beach
- Red Wing Lake Golf Course
- Sarah Constant Beach Park