Waterfront holiday 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.

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Guest favourite

Guest suite in Virginia Beach

4.89 out of 5 average rating, 550 reviews

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.

2–9 Nov

₹7,422 per night

Guest favourite

Cottage in Norfolk

5.0 out of 5 average rating, 249 reviews

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

22–29 Sep

₹17,352 per night

Guest favourite

Tiny home in Hampton

4.92 out of 5 average rating, 171 reviews

Hampton River Retreat Tiny House

Take a romantic getaway in a private, newly renovated tiny home on the river. Located just a short walk to Hampton River Park, guests can enjoy downtown Hampton's great selection of restaurants and bars or visit the white-sand beaches just a short drive away. Rather stay home? Hang out on the patio fully equipped with an outdoor bar and TV. This one-bedroom house is surprisingly spacious— it sleeps up to four adults and has all the amenities needed for a relaxing stay. No parties or events!!

10–17 Oct

₹10,497 per night

Guest favourite

Guest suite in Carrollton

4.98 out of 5 average rating, 160 reviews

2BR 1BA Spacious Guest Suite, Woods & Water Views

NO CLEANING FEES CHARGED! ONLY YOU/YOUR TRAVEL COMPANION ARE GUESTS in the private , in home, upstairs 2 BR 1 BATH UPSTAIRS SUITE W/MINI-KITCHEN. Nothing fancy, but clean, pretty. & relaxingly comfy. Serene, wooded, retreat like setting on a small lake w/wildlife. Centrally located. Visit Williamsburg one day & VA Beach the next. Near Smithfield, universities & military bases. Please read the accommodations policy below before requesting to book. Discount for active military & nurses.

20–27 Feb

₹8,743 per night

Guest favourite

Farm stay in Cape Charles

5.0 out of 5 average rating, 331 reviews

Private Guesthouse on Secluded Waterfront Farm

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 urban centers. Our twenty acre waterfront farm, which has plenty of nearby walking or biking, and a dock onto a secluded arm of Plantation Creek, an inlet of the Chesapeake Bay, is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

5–12 Sep

₹14,945 per night

Guest favourite

Apartment in Virginia Beach

4.88 out of 5 average rating, 175 reviews

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 and towels provided. Please note: due to the open layout of the building, there is no elevator.

7–14 Jan

₹14,989 per night

Guest favourite

Home in Moyock

4.93 out of 5 average rating, 283 reviews

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.

9–16 Nov

₹14,962 per night

Guest favourite

Bungalow in Norfolk

4.97 out of 5 average rating, 159 reviews

Beachfront Bungalow; Amazing views (3bdrm, 2 bath)

We're excited to welcome you to The Pirate's Cove, our Beach Bungalow on the Chesapeake Bay. Enjoy the sunset from the balcony, the primary bedroom or the water facing windows! Gaze at the ships traveling through the bay from the telescope. In the morning, enjoy an espresso or latte at the Coffee Bar as you watch the sunrise. Have all the family fun in the comfortable living room with large screen TV and games. Energize and refresh with hosted snacks and refreshments!

2–9 May

₹28,323 per night

Guest favourite

Cabin in Cape Charles

4.96 out of 5 average rating, 99 reviews

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.

8–15 Nov

₹18,124 per night

Guest favourite

Guest house in Hampton

4.99 out of 5 average rating, 286 reviews

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. (Please also check out our additional property "The Water's Edge"). Sun, Se and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house is 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.

27 Sep – 4 Oct

₹11,229 per night

Guest favourite

Cottage in Norfolk

4.98 out of 5 average rating, 174 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

No congestion, crowds, or commercial big beach resorts here. Experience the exact opposite at Courtyard Cottage just steps away from a quiet and peaceful beach surrounded by sand dunes for a special getaway. A park across the street provides playgrounds and pet-friendly walks and is the home to a local farmers market, 9 a.m. to noon. Saturdays, May 4 through Nov. 23. A past guest wrote "This place brings beach home nostalgia. peace, and a time to relax".

21–28 Feb

₹19,275 per night

Guest favourite

Flat in Virginia Beach

4.87 out of 5 average rating, 151 reviews

Va.Beach/Oceanfront Studio, Boardwalk, Beach, Pool

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 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.

3–10 Dec

₹12,413 per night