Kid-friendly holiday rentals in Chesapeake Beach

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Top-rated family-friendly rentals in Chesapeake Beach

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

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Guest favourite

Cottage

4.96 out of 5 average rating, 165 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.

Guest favourite

Apartment

4.92 out of 5 average rating, 176 reviews

2 Bedroom Condo One Block from the Oceanfront!

Our newly renovated 2 bedroom condo ONE block from the boardwalk accommodates 6 people and is also perfect for families. Each bedroom has a flat screen TV; one with a queen bed and the other with a king bed. There is also a pull out sofa bed in the living room along with a large TV. This is a 2nd floor unit with one designated parking spot. Plenty to do for the whole family with the beach, boardwalk, shopping, restaurants, amusement parks, and many more activities all within walking distance.

Guest favourite

Apartment

4.88 out of 5 average rating, 175 reviews

Oceanfront Jewel VB Studio Mesmerizing Ocean View

Newly remodeled, stunning panoramic oceanfront views from the 3rd floor at the peaceful north end of Va Beach boardwalk. Perfect for two, this cozy 355 sq ft studio with wireless internet, large screen TV and full kitchen, has a community pool, back patio, charming beach lawn with tables & lounge chairs and is walking distance to outstanding restaurants, attractions and shopping. Beach chairs and towels provided. Please note: due to the open layout of the building, there is no elevator.

Guest favourite

Cottage

4.99 out of 5 average rating, 117 reviews

Private Beach Access at The OV Beach House

Here at the OV Beach House, you have your own private access to the beach and STUNNING water views of the Chesapeake Bay. The sunrises and sunsets are incredible! My husband and I renovated the interior of the house this past year. We poured all of our love (and sweat) designing and crafting a home away from home with you in mind!! You'll find the kitchen stocked with all of the essentials. Towels, soap, shampoo, and conditioner are all provided. Can accommodate up to 8 people.

Guest favourite

Home

4.99 out of 5 average rating, 184 reviews

Play by the bay beach house,

Fantastic beach home with 3 bdrms and 3 baths. Renovated Dec2020 Great views of the Chesapeake Bay from the LR and deck. Just steps away from the beach access. Updated with SS appliances. First floor has Living room-dining rm combo with vaulted ceilings, kitchen, bdrm and bathrm. Second floor has 2 bdrms and 2 private baths . TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill. Washer-dryer. ONLY ROOM FOR 2 REGULAR SIZE CARS/SUVS IN DRIVEWAY PLUS FREE ON STREET PARKING.

Guest favourite

Cabin

4.95 out of 5 average rating, 142 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.

Guest favourite

Cottage

4.99 out of 5 average rating, 215 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".

Guest favourite

Apartment

4.95 out of 5 average rating, 101 reviews

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen

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

Guest favourite

Guest suite

4.93 out of 5 average rating, 553 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

Guest favourite

Home

4.91 out of 5 average rating, 238 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.

Guest favourite

Guest suite

4.94 out of 5 average rating, 214 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

Guest suite

4.91 out of 5 average rating, 238 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.