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 in Virginia Beach

4.98 out of 5 average rating, 140 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.

26 Sept – 3 Oct

£273 per night

Guest favourite

Guest suite in Virginia Beach

4.89 out of 5 average rating, 551 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.

4–11 Dec

£85 per night

Guest favourite

Guest suite in Virginia Beach

4.97 out of 5 average rating, 234 reviews

Scott's Garden Suite At The Crooked House

Just blocks from the beach, Scott's Garden Suite is nestled in the back yard of one of southside's desireable neighborhoods. With a spacious, queen bedroom & small reading/sleeping den, this little private hideaway is ideal for 2/3 adults or small family. Adjacent to the ViBe Art District/restaurants/shopping, it has kitchenette, 3/4 bath & outdoor LR with gas fire table. This is a ‘homeshare’ SRT & is within the in-resident owners’ home - separately entranced & private for convenience/safety.

16–23 Sept

£116 per night

Guest favourite

Home in Virginia Beach

4.8 out of 5 average rating, 137 reviews

Beach house for 10 people! 1 block to beach!

Welcome to Ocean Beach House! Nestled right in the heart of Chic's Beach. 3 bedroom 2.5 bath beach house with a large hangout spot in the back yard. Plenty of parking space. Less than a minute walk to the beach. PLEASE DO NOT BOOK this unit if you intend to play loud music or host a gathering. Strict Quiet hours 10pm-8am. By making this booking, you agree to forfeit a minimum of $2500 to deploy private security and/or law enforcement for immediate removal of you/your party from the premises.

23–30 Jun

£513 per night

Guest favourite

Guest house in Norfolk

4.98 out of 5 average rating, 554 reviews

Private Guesthouse, Ghent/Downtown near ODU, EVMS

Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

9–16 Jan

£129 per night

Guest favourite

Guest suite in Virginia Beach

4.98 out of 5 average rating, 278 reviews

Home away from home~Private,quiet, mins to bay

Home away from home is a spacious, comfortable, and private apartment with 1 Queen bedroom, full bath w/ tub, living area, work space, and fully equipped kitchen. Conveniently and centrally located in historic neighborhood: 3 mins to bay, 15 mins to oceanfront. We are within 4 miles of Norfolk Premium Outlets and IKEA, and are within 5 miles to Virginia Wesleyan and 15 miles to ODU. Walk to local favorite restaurants (New River Tap House, The Rustic Spoon, 1608 Crafthouse, Comfy Belly).

5–12 Jul

£171 per night

Guest favourite

Guest suite in Chesapeake

4.95 out of 5 average rating, 479 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

20–27 Sept

£113 per night

Guest favourite

Home in Virginia Beach

4.99 out of 5 average rating, 164 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.

28 Oct – 4 Nov

£312 per night

Guest favourite

Home in Virginia Beach

4.78 out of 5 average rating, 130 reviews

Quaint 2 Bedroom Cottage in Chicks Beach

2 bedroom 1 bathroom quaint cottage, walking distance only 2 blocks to the beach . The beach is great for families with children . This unit is connected to a 1 bedroom unit . Back yard has a single detached unit also . Great for small families. There is a fenced in front yard Back yard and laundry area is shared with guest suite next door. 2 Car max allowed $75 pet fee with pre approval. Starting June 25th 7 night min check in on Friday only !

2–9 Oct

£172 per night

Guest favourite

Home in Virginia Beach

4.9 out of 5 average rating, 207 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.

29 Nov – 6 Dec

£83 per night

Guest favourite

Guest house in Chesapeake

4.98 out of 5 average rating, 215 reviews

Beautiful and Chic, One Room Studio Apartment

Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.

27 Mar – 3 Apr

£89 per night

Guest favourite

Guest suite in Virginia Beach

4.94 out of 5 average rating, 186 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!

7–14 Sept

£192 per night