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Family-friendly holiday rentals in Chesapeake Beach

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Top-rated family-friendly rentals in Chesapeake Beach

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite
Guest suite in Virginia Beach
4.9 out of 5 average rating, 693 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.

Guest favourite
The spacious bedroom features a queen-size bed with a tropical-patterned comforter. A leather sofa is positioned beside a small dining table with two chairs. A surfboard decoratively hangs on the wall, complementing the room's casual beach theme.
Guest suite in Virginia Beach
4.98 out of 5 average rating, 411 reviews

Just Steps Away to the Beach

Enjoy Jan. thru Mar. at Va. Bch--average day temp. mid 50s to 60s. Just steps or bike through a nice area to the beach, restaurants, culture, The Dome, Convention Ctr & other activities. Take a 10-min. walk or bike to the beach (7 short blocks). No traffic or parking hassles! We are close to I264, several military bases & Hilltop Shopping area. This is a quiet neighborhood & convenient location. Perfect for couples & solo travelers. NO animals or pets allowed! NO children under 13 yrs. of age!

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, 199 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
The spacious kitchen features a large island with seating for six, modern appliances, and ample counter space. A bright window above the sink offers views of the surrounding landscape, while soft lighting complements the contemporary design. Light wood flooring enhances the welcoming atmosphere.
Farm stay in Cape Charles
5 out of 5 average rating, 412 reviews

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.

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, 212 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
Home in Virginia Beach
4.87 out of 5 average rating, 201 reviews

Charming Single Family Home by the Chesapeake Bay

Discover your perfect Virginia Beach retreat! This charming, single-family home is nestled in a friendly neighborhood just a mile from the stunning Chesapeake Bay. You're within walking or biking distance of great local breweries, restaurants, and parks, including the Bayside Recreational Center and Bayville Park. This home features a private, fenced-in backyard, perfect for relaxing after a day at the beach or letting small pets run around for an additional fee.

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
4.92 out of 5 average rating, 626 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, 287 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
4.94 out of 5 average rating, 253 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!

Guest favourite
A cozy studio space is showcased, featuring a spacious bed with light bedding and decorative pillows. A comfortable gray couch with assorted cushions is positioned nearby, alongside a wooden coffee table. Wall decor includes a welcome sign and floral art, adding a pleasant aesthetic.
Guest suite in Virginia Beach
4.92 out of 5 average rating, 316 reviews

Cozy Private Studio

Cozy, fully equipped, inviting studio located in the heart of Virginia Beach! Minutes from highway 64. Which gives easy access to anywhere in the Hampton Roads area. 15-20 minute drive to Virginia Beach Ocean front and convention center. 2 minutes from Regent University, CBN and founders in. Soccer complex, Stumpy lake golf course close by. Restaurants and shopping 5 minutes away.

Guest favourite
A hot tub is situated within a wooden gazebo, surrounded by latticework for privacy. The water is invitingly clear and features a center base for comfort. The wooden deck provides ample space for relaxation, with natural greenery visible in the background.
Guest suite in Virginia Beach
4.9 out of 5 average rating, 285 reviews

Rest A’Shore-Virginia Beach

Quaint, quiet, one bedroom in-law suite with kitchenette and private entrance, with owners on premises. Guests have access to a large outdoor area, year-round hot tub, and parking on the premises. Located in the Great Neck corridor of Virginia Beach, just minutes to beach access, Virginia Beach General Hospital, Hwy 264 and plenty of shopping. An ideal stay for 1-2 adults.

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, 151 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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