
Waterfront vacation rentals in Chesapeake
Find and book unique waterfront rentals on Airbnb
Quick stats about waterfront rentals in Chesapeake

Total vacation rentals
Explore 60 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

Verified guest reviews
Over 4,660 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Chesapeake vacation rentals include wi-fi access

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

4.8 Average rating
Chesapeake stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Aerotheater
Top-rated waterfront rentals in Chesapeake
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.
RiverBeachHeating

Sportsman's Paradise ( Hunting & Fishing )
Sportsman's Paradise is just minutes away from the Currituck Sound which is famous for it's duck hunting and fishing. It overlooks Tull's Bay and Tull's Creek and is surrounded by the Northwest River Marsh Game Lands. The kitchen and living room have 9 windows so you can look out three sides of the house at the water. The walls are old rough cut boards and the ceilings are plywood. The living room and bedrooms are carpeted and the bathrooms and kitchen are laminate wood floor.
RiverBeachQuiet

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.
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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!
RiverBeachWalkability

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. Bring your fishing poles!
RiverBeachLayout

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.
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Beachfront Exclusive Bay front Suite
This comfortable private beachfront suite with a kitchenette offers breathtaking 180-degree views of the Chesapeake Bay. Enjoy magnificent sunrises and stunning sunsets from your private deck, with the water’s edge just steps away. If you’ve ever wanted to experience life on the beach, this is as close as it gets. This suite reflects our love for the Chesapeake Bay and the relaxed coastal lifestyle, and we’re conveniently located just 10 minutes from ORF Airport
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Villa Positano
This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.
BeachViewLaundry

R & R River House
Have a peace of mind when you rent this luxury condo with beautiful water views. Totally remodeled condo with high-end finishes. This home is perfect for a couple getaway or family for fun with the nearby city park (1 mi). The peaceful condo is located close to the Casino (4.5 mi), Downtown Portsmouth (7 mi), Waterside (7.6 mi), and Virginia Beach (25 mi). Be amazed with this nestled away condo in safe neighborhood.
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Beachfront stay with kayaks & paddleboards
Private beach access, Chesapeake Bay views, and kayaks and paddle boards included. This waterfront home is made for slow mornings, beach days, sunset evenings, and time on the water. My husband and I renovated the interior ourselves with comfort and simplicity in mind. The kitchen is stocked with the essentials, and towels, soap, shampoo, and conditioner are provided so you can settle in easily and enjoy the bay.
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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.
BeachViewFamily

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.
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Popular amenities for Chesapeake waterfront rentals
Waterfront apartment rentals

VB Oceanfront Studio Balcony,Beach,Boardwalk, Pool
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Oceanfront Building Boardwalk Pool Beach 3 Beds
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Beach Nut - Virginia Beach Oceanfront!
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The Southern Magnolia | 2br/1bth Home
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North End Oceanfront Condo with Balcony
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The Lighthouse-2 blocks to beach
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New! Oceanfront Penthouse/ 2 Decks/ Pool/Beach/Gym
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Sunset Retreat
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Waterfront house rentals

PETS Welcome! 4Bed Beach View Privately Managed
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*Semi-Priv Beach*King Bed* Waterfront*EV Charger
RiverBeachAccuracy

New Beach Home on the Chesapeake Bay
BeachViewWifi

One block from the Beach
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Lakefront House @ Oceanfront
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Bayfront Pool Retreat, Walk to Beach
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2 Min Walk to Beach • Fenced Yard • Parking
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Beachfront 2 Dwellings EV charger
BeachViewAccuracy
Waterfront condo rentals

Cher's Place @ The Beach
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Ocean Escape
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3bd Sandbridge - Sunset Bay views! Newly Remodeled
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Tropical 2BR Condo Getaway 1 Block from the Beach!
BeachFamilyComfort

Oceanfront Penthouse
BeachViewGetting around

Paradise at the Beach
BeachSleep qualityAccuracy

Oceanfront, beach, boardwalk, fun, dolphin, sunris
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Oceanfront Gem VaB Studio Exceptional Views
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When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 367 | ﺩ.ﺇ 367 | ﺩ.ﺇ 474 | ﺩ.ﺇ 474 | ﺩ.ﺇ 474 | ﺩ.ﺇ 499 | ﺩ.ﺇ 477 | ﺩ.ﺇ 452 | ﺩ.ﺇ 397 | ﺩ.ﺇ 404 | ﺩ.ﺇ 367 | ﺩ.ﺇ 411 |
| 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 |
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- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Buckroe Beach
- Carova Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Old Dominion University
- Norfolk Botanical Garden
- Regent University
- First Landing Beach
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Currituck Beach Lighthouse
- The Mariners' Museum
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- Town Point Park
- Nauticus
- Chrysler Museum of Art
- Hampton University





