Holiday houses in Holly Bluff Island

Guest suite in Virginia Beach

4.9 out of 5 average rating, 645 reviews

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.

Farm stay in Cape Charles

5 out of 5 average rating, 384 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 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.

4.93 out of 5 average rating, 245 reviews

Loft in Cape Charles

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.

Townhouse in Cape Charles

4.95 out of 5 average rating, 145 reviews

3 Blocks to Beach, Fenced Backyard, Pet Friendly!

Welcome to Peach Haven, a newly renovated duplex in the Cape Charles historic district. Just 1 block from the park and 3 blocks from the beach, it's the ideal base for your Cape Charles escape. This pet-friendly rental sleeps five guests comfortably with a master bedroom (queen bed) and a second bedroom with a custom-made full-over-full bunkbed. The house has been thoughtfully stocked with everything you'll need for a comfortable stay. Need more space? Ask about renting the other side, too!

4.97 out of 5 average rating, 116 reviews

Wander 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.

Tiny home in Cape Charles

4.98 out of 5 average rating, 317 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.

4.96 out of 5 average rating, 176 reviews

Cabin in Cape Charles

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.

4.96 out of 5 average rating, 122 reviews

Home in Gloucester Point

Charming coastal home w/ outdoor area and river views

Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the historic triangle, or just take it easy around the house and enjoy the outdoor area, the choice is yours.

4.96 out of 5 average rating, 253 reviews

Steps to the Sea at Salt Box

Escape to The Salt Box, a charming 1915 duplex just one block from the beach in the heart of Cape Charles' Historic District. This cozy, private retreat sits on a peaceful, tree-lined street and is a short stroll to the beach, pier, shops, restaurants, and more! Check out our local Guidebooks or text us anytime—we're happy to share our favorite local spots! Looking for even more space? You can also book the other half of our duplex, Salt Box II!

4.92 out of 5 average rating, 256 reviews

Home in Virginia Beach

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.

4.99 out of 5 average rating, 348 reviews

Guesthouse in Hampton

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. Sun, Sea and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house 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.

Guest suite in Machipongo

5 out of 5 average rating, 107 reviews

Peaceful Suite in Machipongo

Welcome to our soul-nourishing space perfect for your getaway! A magical place where time seems to stand still in the peace and tranquility. Nature beckons as birds fly back and forth, chimes sing in the breeze, stars glisten in the sky. Welcome to Feather Tree Retreat, a refreshing haven on the Eastern Shore of Virginia!

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Popular amenities for Holly Bluff Island holiday rentals

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Other great holiday rentals in Holly Bluff Island

4.85 out of 5 average rating, 27 reviews

Serenity and Luxury Awaits near the Beach

ToddRating, 5 stars33 months ago

The stay was great and we were happy to spend another short vacation at the camper. The wifi was a great addition and repairs to the stairs made it easier to access.

5 out of 5 average rating, 5 reviews

Home in Virginia Beach

941 Coastal Luxury Retreat

Sarah and CoreyRating, 5 stars4 days ago

It was a great place to stay! Super clean and comfortable. Many great places with if walking distances or a short drive. The farmer’s market is a must do! Carrie was super helpful with a question during the stay. We would stay again!

5 out of 5 average rating, 3 reviews

Holiday Blues vacation rental

TeresaRating, 5 stars2 weeks ago

We enjoyed our stay. House was very nice . Really liked having three full bathrooms. Will differently stay here again and recommend to anyone. Kitchen furnished nicely and had toiletries .

Home in Gloucester County

4.95 out of 5 average rating, 56 reviews

York River | Chesapeake Bay Bliss: Fishing Retreat

MagdaRating, 5 stars2 months ago

Our family of four loved staying here. Our 10-year-old delighted in crabbing and playing board games (chess and Battleship). Our 7-year-old desperately wanted to splash around the York River even though it was freezing in April. The local recommendations were much appreciated and the impact of staring at a horizon line cannot be overestimated.

Cabin in Cape Charles

4.75 out of 5 average rating, 4 reviews

Oyster Point Cabin

KeiraRating, 5 stars1 month ago

This place was amazing for our small getaway, the people were so friendly and helpful.

5 out of 5 average rating, 11 reviews

Fisherman's Getaway

MichaelRating, 5 stars1 week ago

Been fishing in Cape Charles for some time, found this place for a last minute trip. Cameron and Alexandra were great at getting me in last minute, quick to get back with me for any questions before and during my stay. Place was in a great location and very clean, will definitely be using it again for future trips to Cape Charles!

Home in Norfolk

5 out of 5 average rating, 4 reviews

Casa del Mar - Bold, Bright & Steps to the Sand!

JonquilRating, 5 stars1 week ago

Carlos went above and beyond hosting us! He is very friendly and has excellent local recommendations. We rented unit B and were not disappointed. It's only a short walk to the beach and is very peaceful. We would definitely stay here again! Absolutely zero complaints!