Holiday rentals in Chesapeake Beach

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Top-rated holiday rentals in Chesapeake Beach

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Top guest favourite
Guest suite in Virginia Beach
4.9 out of 5 average rating, 715 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.

Top guest favourite
The front entrance features a ramp leading to a bright blue door surrounded by large windows. The white exterior of the house is complemented by landscaping with green shrubs and a sunny sky overhead, enhancing the welcoming appeal.
Cottage in Virginia Beach
4.97 out of 5 average rating, 206 reviews

The Seaglass Cottage by the Chesapeake Bay

The Seaglass Cottage by the Bay is located in the charming & beautiful neighborhood of Ocean Park just a quick 5-10 minutes stroll to the Chesapeake Bay beach. Our vintage beach house from the 1940’s has been fully remodeled and decorated in local art and beach décor. There are beautiful live oaks on the property and 3 private parking spaces for you and some first-come-first-serve street parking in front of the house. Easy load in with a ramp into the house and a mudroom for all your beach toys.

Top guest favourite
A serene sunset view is captured over the Elizabeth River, with vibrant hues of orange and pink filling the sky. Silhouetted trees frame the scene, while a peaceful dock extends into the water, inviting moments of reflection and tranquility.
Cottage in Norfolk
5 out of 5 average rating, 290 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

Top guest favourite
Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.
Home in Norfolk
4.97 out of 5 average rating, 124 reviews

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!

Top guest favourite
A tranquil beach scene is captured, featuring smooth sandy stretches bordered by green grass and gentle dunes. The horizon reveals a calm ocean meeting a partly cloudy sky, creating a serene atmosphere that invites relaxation and reflection.
Cottage in Norfolk
4.99 out of 5 average rating, 293 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

There is no congestion, crowds, or large commercial beach resorts here. Experience the exact opposite at Courtyard Cottage, steps away from a quiet, peaceful beach surrounded by sand dunes for a special getaway. A park across the street offers playgrounds and pet-friendly walks, and a local farmers' market opens from 9 a.m. to noon. Saturdays, May 4 - Nov 23. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax". No parties, quiet hours after 10 pm.

Top guest favourite
The Airstream is surrounded by tall trees, with a spacious deck featuring comfortable seating arrangements. Oversized Adirondack chairs and a large sofa face the natural scenery. Soft lighting adds warmth, enhancing the outdoor experience in a peaceful, wooded setting.
Farm stay in Cape Charles
4.96 out of 5 average rating, 270 reviews

Airstream Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning Airstream retreat 10 mins from Cape Charles. The 1969 Airstream has been converted into a contemporary studio with all the comforts of a luxury hotel room. Wake up to the birds singing in the trees that completely surround the huge front deck. Take a walk on our trails. Enjoy watching the animals. Take a trip into Cape Charles for restaurants and shopping, then enjoy a movie in the Airstream at night.

Top guest favourite
A sandy beach stretches into the distance, bordered by gentle dunes and green grasses. A wooden walkway leads to the shore, where several figures can be seen walking. The calm ocean reflects the blue sky, dotted with fluffy white clouds.
Home in Virginia Beach
4.99 out of 5 average rating, 216 reviews

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.

Guest favourite
A two-story townhome displays a modern exterior with gray and white siding. A welcoming front porch features a white railing and two entrance doors. A colorful flag adds a cheerful touch, while a privacy fence is visible in the background.
Townhouse in Virginia Beach
4.92 out of 5 average rating, 122 reviews

Beach Livin' by the Chesapeake Bay - VA Beach

Beach livin' just a few short blocks to the Chesapeake Bay, Beach & great restaurants.. Tastefully decorated - all the amenities. 6 person farmhouse table. Deck has table & chairs, grill. Privacy fenced backyard. Beachcart, chairs, towels, umbrella & sand toys. 2 queen beds & 2 bunk beds. Cozy livingrm w/loveseat, wicker chair, wicker swivel rocker, barstools, smart tv with basic cable. Base Rate includes 9% VA Beach occupancy tax and Lodging room tax

Top guest favourite
Two comfortable white Adirondack chairs are positioned on a wooden deck, facing the peaceful expanse of the Chesapeake Bay. The scene includes soft grass in the foreground and a clear sky above, creating a serene viewing spot for enjoying the beach.
Guest suite in Norfolk
4.93 out of 5 average rating, 643 reviews

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.

Top guest favourite
A beach scene at sunset features individuals playing volleyball in the sand. The calm water reflects shades of pink and orange from the setting sun. Silhouettes of a pier and distant structures are visible along the horizon, framed by beach grass in the foreground.
Home in Virginia Beach
4.93 out of 5 average rating, 294 reviews

Quilted Quarters by the Bay with Private Entrance

Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.

Top guest favourite
A vibrant sunset is captured over the water, casting a warm glow as it descends behind a distant pier. Silhouetted figures walk along the sandy shore, with gentle waves lapping at the beach. Soft hues of orange and pink fill the sky, creating a serene atmosphere.
Guest suite in Virginia Beach
4.93 out of 5 average rating, 257 reviews

Enjoy your little slice of heaven in Chics Beach!

4-5 min walk to Chic's beach. Avoid the crowds and live with the locals! Surrounded by amazing restaurants, bars, coffee shops, and even an urban winery. We are a convenient 15 min ride from the tourist Oceanfront but you will have plenty to do in our relaxed beach town. This is a guest apartment attached to my home .The motto of Chic's Beach is "No Bad Days". Come see for yourself!

Top guest favourite
An aerial view captures the surrounding area, featuring a mix of residential homes and lush greenery with sandy beach access visible. The Chesapeake Bay Bridge-Tunnel stretches toward the horizon over calm waters, providing a scenic backdrop to the coastal neighborhood.
Home in Virginia Beach
4.97 out of 5 average rating, 154 reviews

Water Oaks at Chic's Beach

Bright, airy beach home across the street from the Chesapeake Bay beach, a quarter mile east of the Chesapeake Bay Bridge-Tunnel . . . 1600 sf, 3 br, 2.5 ba . . . eclectic residential neighborhood . . . diverse restaurants and a convenience store within easy walking distance . . . five-minute drive from more comprehensive shopping and fifteen minutes from VB oceanfront.

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