
Waterfront vacation rentals in Chesapeake
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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.

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.

Guesthouse at Vessel Farm & Winery, Waterfront
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.

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

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.

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 spacw to spread out, this is IT! Convenient to Virginia Beach Oceanfront, Downtown Norfolk, Rivers Casino, Waterside District & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect for holiday family & group trips, 12 minutes from Carnival Cruise Half Moon port.🛳🌊🚢🏠😊!

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.

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!

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.

The Cottage on Sarah's Creek
Nestled on the waters of Sarah's Creek, this cozy cottage is just a short drive from historic Williamsburg and Yorktown. Fully furnished with a new kitchen, dining area, 1 bedroom, 1 bathroom, and a large loft with a queen bed and a pool table. Whether spending your days relaxing on the beach, exploring historic sights, or taking a tour of a local vineyard, you can look forward to the quiet comfort this cottage has to offer during your stay.

Beachfront Exclusive Bay front Suite
This comfortable private beachfront suite with kitchenette has magnificent views of the sunrise and sunset that you can enjoy from your own private deck, with a 180 degree views of the beach front with easy access to the water's edge, just steps away. If you want to experience life on the beach this is as close as you can get. This suite represents our personalities and everything we love about living at the beach on the Chesapeake Bay
Popular amenities for Chesapeake waterfront rentals
Waterfront apartment rentals

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

Yorktown on the Waterfront

Oceanfront 2 bedroom condo

The Coastal Studio

Oceanfront Building Boardwalk Pool Beach 3 Beds

Works 4 Me: New listing

Bayside condo on the beach in Sandbridge

Luxury Oceanfront Stay • 2BR/2BA + Balcony
Waterfront house rentals

*Escape to the Tangerine Dream*

Steps to Beach at Chics Beach! Sleeps 12 & Garage!

New Beach Home on the Chesapeake Bay

Amazing Gem! Riverfront, Location, Sunsets, Quite

Bay view | 3BR House | Hot Tub & Private Dock

8br, Pool, Lzy Rvr, Pier, Pool, Hot Tub (Sandbridge)

Escape to the water!

Stunning Views of Back Bay & Seconds to the Beach
Waterfront condo rentals

Bay Breeze At Ocean View Beach Home

Beach Luxury Beachfront

Oceanfront Gem VaB Studio Exceptional Views

Paradise at the Beach

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Beachfront Getaway, Pet Friendly, Dolphin Suite

OBC - 1BR/1BA - Partial Ocean View - Great Pools!

2 Bedroom Stylish Kingsmill condo
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$23,223 GYD | G$22,177 GYD | G$24,269 GYD | G$23,014 GYD | G$24,060 GYD | G$26,152 GYD | G$27,198 GYD | G$25,734 GYD | G$22,596 GYD | G$22,596 GYD | G$21,131 GYD | G$20,922 GYD |
| 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 vacation rentals
Explore 60 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at G$6,277 GYD per night before taxes and fees

Verified guest reviews
Over 3,520 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
50 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 Cinema Cafe-Greenbrier Mall
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- Waterfront rentals Virginia
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- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Jamestown Settlement
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- Chrysler Museum of Art
- Cape Charles Beachfront
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- Wilkins Beach
- Red Wing Lake Golf Course
- Little Creek Beach




