
Waterfront holiday rentals in Chesapeake Beach
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Chesapeake Beach
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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.

Private apartment only 3 blocks from the Beach
Newly remodeled, super clean one bedroom (in-law) apartment, approx. 375 sf. Three blocks from the beach 7-10 min walk. Covered deck, backyard on water to watch ducks, herons, fish. Concrete benches and firepit near the water. Walking distance to the ocean, boardwalk, Rudee Inlet, dining and entertainment. Hardwood floors, queen size bed, 'pack n play', kitchenette with sink, refrigerator, microwave, Keurig coffee maker, toaster (no oven or stove) 1 gig mbps Wifi, internet tv. Futon-like couch.

Oceanfront Gem VaB Studio Exceptional Views
Newly renovated modern studio condo, owners personal getaway now open to guests. This corner unit, the largest and most private in Oceans ll Condominium complex, is on the 3rd floor and offers beautiful, expansive views at both sunrise and sunset. Just off the boardwalk with community pool, this unit sleeps three. Right on the oceanfront, you won't find a more peaceful getaway! Beach chairs & towels provided in season. Please note: due to the open layout of the building, there is no elevator.

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

THE POINT! Private waterfront Oasis!
Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

Penny’s Palace 1 Bed/1 Bath Home
Welcome to Penny’s Palace! A charming home nestled in quiet community of Portsmouth, VA. Entire home for you with sectioned off suite and bathroom. Penny’s Palace is vibrant & elegantly furnished yet practically designed to sleep 2 people comfortably. This bungalow offers an outdoor sitting area with a dreamy lighted canopy & outdoor grill. It’s perfectly located minutes from major Hampton Roads attractions: Olde Town Portsmouth, Children’s Museum, Downtown Norfolk, Casino, and Virginia Beach.

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

Beach Front with Paddle Boards and Kayaks
You have your own private access to the beach AND water views of the Chesapeake Bay that no other home in the area has. The sunrises and sunsets are breathtaking! Paddle boards and kayaks are provided. My husband and I renovated the interior of the house this past year. We poured all of our love (and sweat) designing and crafting a home away from home with you in mind!! You'll find the kitchen stocked with all of the essentials. Towels, soap, shampoo, and conditioner are all provided.

Play by the Bay 1 MIN TO WATER
LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill, Washer-dryer. Great water views while you are relaxing on the deck. Many amenities! Just bring your bathing suit. Our guests have all said they love this place! Very close to many wedding venues, restaurants, state park, oceanfront boardwalk is closeby, military bases, etc.

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony
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 on the balcony 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.

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.

Quaint and Comfortable Buckroe Beach Getaway.
Our quaint, cozy and comfortable, 1,100sf house is perfect for a small family or small group of friends, 4 guests MAX, to relax from the hustle and bustle of life. Take a nap or watch a movie while relaxing on the cozy and comfortable power reclining living room furniture. Enjoy the patio and firepit in the spacious fenced backyard. This getaway is located a short two-minute car ride or ten-minute walk from the beautiful and family-friendly Buckroe Beach.
Popular amenities for waterfront rentals in Chesapeake Beach
Waterfront apartment rentals

Serene Tree House Retreat | Spacious 1br/1bth Home

FourSailsResort Double Balcony OceanfrontJettedTub

Yorktown on the Waterfront

Sandbridge Beach Bay Getaway

Bayside condo on the beach in Sandbridge

Oceanfront 2BR Luxury • Private Balcony

Beach Luxury Oceanfront

Four Sails - 1B/1BA - X-Large Oceanfront Balcony!
Waterfront house rentals

Adams Shore

Oceanfront Cozy Beach Duplex

R & R River House

New Beach Home on the Chesapeake Bay

Chesapeake Bay Retreat Waterfront Indoor Pool

“Vitamin Sea” Waterfront GVI Retreat!

Sunset Sanctuary on the Water- Fast Wifi/Netflix

The Hamptonian - Stylish 4 Bedroom/2 Bath Rancher
Waterfront apartment rentals

Bay Breeze At Ocean View Beach Home

Cher's Place @ The Beach

Tropical 2BR Condo Getaway 1 Block from the Beach!

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Paradise at the Beach

Coastal Beach condo-amazing view and indoor pool

Kingsmill Resort Business Class - Great Monthly

1b/1bath beach condo, unobstructed ocean views
Destinations to explore
- New York City Holiday rentals
- East River Holiday rentals
- Washington Holiday rentals
- Jersey Shore Holiday rentals
- Myrtle Beach Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Cape Fear River Holiday rentals
- Jersey City Holiday rentals
- Rentals with a fireplace Chesapeake Beach
- House rentals Chesapeake Beach
- Townhouse rentals Chesapeake Beach
- Rentals with outdoor seating Chesapeake Beach
- Hotel rooms Chesapeake Beach
- Rentals with a washing machine and dryer Chesapeake Beach
- Rentals with pools Chesapeake Beach
- Rentals with beach access Chesapeake Beach
- Flat rentals Chesapeake Beach
- Rentals with a patio Chesapeake Beach
- Beachfront rentals Chesapeake Beach
- Pet-friendly rentals Chesapeake Beach
- Family-friendly rentals Chesapeake Beach
- Fitness-friendly rentals Chesapeake Beach
- Waterfront rentals Virginia Beach
- Waterfront rentals Virginia
- Waterfront rentals United States
- Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Living History Museum
- Old Dominion University
- Colonial Williamsburg's Merchants Square
- Nauticus
- Virginia Zoological Park
- Town Point Park
- First Landing Beach
- Currituck Beach Lighthouse
- Chrysler Hall
- Currituck Club




