Vacation rentals in Holly Bluff Island

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Top-rated vacation rentals in Holly Bluff Island

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Guest favorite

Guest suite in Virginia Beach

4.97 out of 5 average rating, 234 reviews

Scott's Garden Suite At The Crooked House

Just blocks from the beach, Scott's Garden Suite is nestled in the back yard of one of southside's desireable neighborhoods. With a spacious, queen bedroom & small reading/sleeping den, this little private hideaway is ideal for 2/3 adults or small family. Adjacent to the ViBe Art District/restaurants/shopping, it has kitchenette, 3/4 bath & outdoor LR with gas fire table. This is a ‘homeshare’ SRT & is within the in-resident owners’ home - separately entranced & private for convenience/safety.

Sep 18 – 25

R2,012 ZAR per night

Guest favorite

Loft in Cape Charles

4.92 out of 5 average rating, 204 reviews

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.

Sep 21 – 28

R1,904 ZAR per night

Guest favorite

Farm stay in Onancock

4.99 out of 5 average rating, 174 reviews

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!

Nov 27 – Dec 4

R3,402 ZAR per night

Guest favorite

Farm stay in Cape Charles

5.0 out of 5 average rating, 331 reviews

Private Guesthouse on Secluded Waterfront Farm

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 urban centers. Our twenty acre waterfront farm, which has plenty of nearby walking or biking, and a dock onto a secluded arm of Plantation Creek, an inlet of the Chesapeake Bay, is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Aug 30 – Sep 6

R3,480 ZAR per night

Guest favorite

Home in Cape Charles

4.99 out of 5 average rating, 104 reviews

Modern Private Beach House close to Cape Charles

A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

Dec 17 – 24

R15,705 ZAR per night

Guest favorite

Cottage in Gloucester

4.97 out of 5 average rating, 194 reviews

"Bee Haven" Cottage Retreat

Curious about what makes Gloucester so wonderful? Live like a local at "Bee Haven Retreat" and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Feb 19 – 26

R2,244 ZAR per night

Guest favorite

Tiny home in Cape Charles

4.98 out of 5 average rating, 273 reviews

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.

Dec 1 – 8

R4,822 ZAR per night

Guest favorite

Cabin in Cape Charles

4.96 out of 5 average rating, 98 reviews

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.

Nov 6 – 13

R4,152 ZAR per night

Guest favorite

Guesthouse in Hampton

4.99 out of 5 average rating, 286 reviews

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. (Please also check out our additional property "The Water's Edge"). Sun, Se and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house is located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High speed fiber-optic wifi and cable with blue ray player provided.

Oct 4 – 11

R2,573 ZAR per night

Guest favorite

Apartment in Virginia Beach

4.9 out of 5 average rating, 186 reviews

VB Oceanfront Studio Balcony,Beach,Boardwalk, Pool

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family

Jan 12 – 19

R2,168 ZAR per night

Guest favorite

Cottage in White Stone

4.91 out of 5 average rating, 298 reviews

The Moore Cottage

The Moore Cottage is a rustic-chic, fisherman's cottage.The cottage is less than a mile from Windmill Point Marina, and five miles from the town of White Stone. You will enjoy the views of amazing wildlife, boaters, the beach, and breath-taking sunsets all while sitting on the back porch. The Cottage is nestled on a cove overlooking Little Bay and the mouth of Antipoison Creek. Come check out one of the Northern Neck's best kept secrets!

Sep 23 – 30

R2,298 ZAR per night

Guest favorite

Home in Virginia Beach

4.9 out of 5 average rating, 207 reviews

Quilted Quarters by the Bay with Private Entrance

Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.

Dec 17 – 24

R1,668 ZAR per night