
Waterfront holiday rentals in Chesapeake
Find and book unique waterfront accommodation on Airbnb
Top-rated waterfront accommodation in Chesapeake
Guests agree: These waterfront accommodation options 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.

Church's Island Carriage House
Welcome to Church's Island Carriage House, located on the Currituck Sound directly across from the Corolla Lighthouse. Watch the the sun rise over a panoramic view of the Currituck Sound from your private balcony as you enjoy your morning coffee. It's the perfect set up for a single or couple with separate bedroom, bath, living area and kitchenette. The apartment is up one fight of stairs. Private and located in the quaint community of Waterlily just 30 minutes from OBX and the Virginia line.

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.

*Beautiful Water Views* King Bed*Fast WIFI
Do you desire Peace, Quiet & Tranquility? This townhome is the PERFECT getaway! It's RIGHT on the water and features the following: *Newer Furnishings! *Blazing Fast Panoramic WIFI & Dedicated Workspace *Bedroom 1: KING size bed overlooking the water. Not a bad way to wake up?!? *Gourmet Kit w/Granite Countertops, Stainless Steel Appliances, complete w/a Convection Oven & Coffee Maker & Creamers * Smart TVs w/Adjustable Wall Mounts for your view preference, in Each Bedroom & Living Room.

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.

Island Lotus Yoga & Spa
A nature lover’s dream! Waterfront, ample natural light, serene beauty, and privacy can be all yours at our charming ranch right on the bay. The bay faces east, giving you the most breathtaking views of the sunrise and moonrise. Relax in the spa, adventure on kayaks, and chill and grill over the fire-pit. You’ll also local fresh eggs, and a private yoga class. Check us out on insta @islandlotusyoga! PS we’re not actually an island. Reach us by driving through Virginia Beach!

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.
Popular amenities for Chesapeake waterfront rentals
Waterfront apartment accommodation

LA Bella Beach House (2 bedrooms)

The Southern Magnolia | 2br/1bth Home

Yorktown on the Waterfront

The Coastal Studio

Sandbridge Beach Bay Getaway

Oceanfront 2BR Luxury • Private Balcony

Beach Luxury Oceanfront

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

Private Beachfront Modern Villa: Outdoor Shower!

New Beach Home on the Chesapeake Bay

Amazing Gem! Riverfront, Location, Sunsets, Quite

Escape to the water!

The Hamptonian - Stylish 4 Bedroom/2 Bath Rancher

Quaint and Comfortable Buckroe Beach Getaway.

Riverfront Home w/ Vintage Vibes

Relaxing Luxurious Waterfront
Waterfront condo accommodation

Bay Breeze At Ocean View Beach Home

Tropical 2BR Condo Getaway 1 Block from the Beach!

Comfy 1BR w pond view Kingsmill

Ocean & Bay Views - Local Family Owned & Operated

Paradise at the Beach

Oceanfront, beach, boardwalk, fun, dolphin, sunris

2 Bedroom Stylish Kingsmill condo

1b/1bath beach condo, unobstructed ocean views
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $156 AUD | $149 AUD | $163 AUD | $155 AUD | $162 AUD | $176 AUD | $183 AUD | $173 AUD | $152 AUD | $155 AUD | $141 AUD | $158 AUD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Quick stats about waterfront rentals in Chesapeake

Total holiday rentals
Explore 60 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $42 AUD per night before taxes and fees

Verified guest reviews
Over 4,370 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Chesapeake holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake rentals

4.7 Average rating
Chesapeake stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square
Destinations to explore
- New York City Holiday rentals
- Washington Holiday rentals
- Jersey Shore Holiday rentals
- Myrtle Beach Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Cape Fear River Holiday rentals
- Jersey City Holiday rentals
- Rappahannock River Holiday rentals
- James River Holiday rentals
- Rentals with a kayak Chesapeake
- Rentals with outdoor seating Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with beach access Chesapeake
- House rentals Chesapeake
- Beach house rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Condo rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with lake access Chesapeake
- Fitness-friendly rentals Chesapeake
- Townhouse rentals Chesapeake
- Beachfront rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with pools Chesapeake
- Cottage rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Apartment rentals Chesapeake
- Guesthouse rentals Chesapeake
- Rentals with breakfast Chesapeake
- Waterfront rentals Virginia
- Waterfront rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Outlook Beach
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Town Point Park
- First Landing Beach
- Virginia Living History Museum
- Old Dominion University
- Nauticus
- Currituck Beach Lighthouse
- Chrysler Hall
- Hampton University
- Currituck Club




