Holiday houses in Willoughby Bay

Romantic Sailboat Experience + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

Beautiful Cottage Waterfront Near Downtown Norfolk

A Beautiful Secluded Paradise! We respond quickly This spacious Non-Smoking cozy cottage has a great view of the Elizabeth River. It's 5 miles from downtown Norfolk and a 5 minute walk to a lightrail stop nearby. A day pass is $4.50 including a ferry to Portsmouth. Great amenities Renovated interior Beautiful Fireplace New floor/fully equipped kitchen Fresh organic eggs/yogurt/snacks/juice/coffee included WiFi-CableTV/HBO Bluetooth sound bar Luxury linens New waterview sunroom Washer/dryer

One block from the Beach

Stay at one of the highest rated homes in Willoughby Beach. It has everything you need to have a relaxing getaway. Enjoy the breezes of the Willoughby Bay on the back 2 decks, and the Chesapeake Bay on the front 2 decks. 500 ft walk to Chesapeake beach access, and an outdoor shower ready when you return. We have been hosting since 2018 and you can read our reviews to see that this property is our pride and joy. Let us show you what a five star experience is on Airbnb... Mandy and Kevin

Pet Friendly Beach King Bed

Welcome to Your Vibrant Beach Hideaway! Escape to your own slice of paradise in this vibrant 900 sq. ft. beach bungalow, just 1 mile from Ocean View Beach. Enjoy a peaceful fenced backyard, fire pit, and grill—perfect after a day in the sun. Skip the crowds of VA Beach Oceanfront and unwind in style. With bold design, modern comforts, and beachy charm, this cozy retreat offers the perfect mix of privacy and convenience. Norfolk is a military town you may experience the sound of aircraft.

Quiet East Beach Bungalow, 1 block to beach!

Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

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.

Sunset Sanctuary on the Water- Fast Wifi/Netflix

Escape to this 3 BEDS/2 BATH Sunset Sanctuary on the Water, a peaceful retreat where breathtaking sunsets meet serene waterfront views. Perfect for relaxation, this home offers comfort and charm with cozy living spaces and a welcoming atmosphere. Enjoy coffee on the deck, unwind by the water, or explore nearby attractions. Ideal for families or friends seeking a quiet getaway, our sanctuary blends natural beauty with modern convenience for a truly memorable stay.

The Chesapeake St Retreat - Pet and Kid Friendly!

The kid and pet friendly retreat your family will love! This beautiful 2,200 sqft, four bedroom home is PERFECT for your beach get away and is less than a 5-minute walk from the beach. This home features a stylish design, a dining room table that can seat up to 10, a fenced in back yard for your furry friends. There are two decks with outdoor seating, modern washer and dryer, games and toys, and much much more. Can't wait to host you!!

Norfolk Beach Casita | Fenced Yard | Dog Friendly

🏡 Unique Spanish-style Norfolk vacation home 🐶 Dog-friendly stay with fenced backyard 🌿 Private patio and outdoor seating area 🛋 Bright living room with vaulted ceilings 🍽 Open dining space perfect for gathering 🍳 Full kitchen for easy home-cooked meals 🚗 Easy access to highways and downtown Norfolk 🌊 Less than 2 miles from the beach 🛒 Close to grocery stores and restaurants 👨‍👩‍👧 Comfortable space for up to 4 guests

Beachfront Getaway, Pet Friendly, Mermaid Suite

Escape to a serene, semi-private beach with breathtaking views and everything you need for the perfect vacation. Welcome to Big Blue, where unforgettable memories await. Beach access, Fully stocked kitchen, modern upgrades, comfy beds, large open floor plan, bbq pit, outdoor patio, beach gear & many personal touches. Condo not suitable for children under 7. Pet fee $100 for max of 2 with approval.

*Escape to the Tangerine Dream*

**ESCAPE TO THE TANGERINE DREAM** in this stunning beachfront oasis, located just steps away from the sandy shores of Captain's Quarters Park, this 3 bedroom/2 bath home offers the perfect blend of luxury and relaxation. Step inside to the open concept living area which boasts breathtaking views from two balconies, perfect for enjoying your morning coffee or watching the sunset over the ocean.

Bayfront backyard with a dock, 3BR, Dogs Welcome!

Welcome to our cool and cozy 3 bedroom, 2 bath home in Norfolk! Featuring a king bed and 2 queens, it’s ideal for families traveling together. Enjoy a fully stocked kitchen, Wi-Fi, Smart TV, and laundry! Located in the Willoughby neighborhood of Norfolk, you’ll have easy access to the ocean and all Norfolk has to offer. Whether for a weekend or an extended stay, this home has it all!