
Family-friendly vacation rentals in Chesapeake
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Top-rated family-friendly rentals in Chesapeake
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Popular amenities for Chesapeake family-friendly rentals
Family-friendly home rentals with a pool

Williamsburg Vacation Villages 4BR, 4BA
We booked Vacation Village 4br timeshare through Andy but it was full. Andy was able to leverage his connections and find us a 3br HOUSE at Kings Creek Plantation through Spinnaker which was better, I think! We had a full 3br/4bath house to ourselves with three porches in a peaceful setting. Absolutely recommend Kings Creek Plantation through Andy. Close to everything and amazing setting. So quiet and pencil. We will be back!

*Historic Powhatan Resort- 2 bedroom
It was a perfect little get away, while learning colonial history! Definitely recommend coming back when it is warmer out!

Westgate Historic Williamsburg One Bedroom
We had a great stay at Eddie's place! Very close to restaurants, Colonial Williamsburg, and Busch Gardens. The unit we stayed in was spotless and had all of the amenities that we needed during our stay. Highly recommended!

Breathtaking Ocean views at Pinch Me, 8bdrm, 6bath
Beautiful home in a wonderful location. Tanya was very friendly and communicative throughout the process.

POOL, Pool House, Hot Tub, Grill, 2 bedroom
He was so nice and everything!!

Timeshare Kingsgate Resort- 2 bdrm
I appreciate Brooke for her very timely customer service & response time. I originally tried to book with another host within the same resort and he was so nasty, that I wasn't going to look again within this resort. I looked again and it was GOD who guided my fingers to her listing. I'm glad I didn't give up and So glad Brooke was the Angel to respond IMMEDIATELY! Brooke Send me all your listings so I can book with you again! LOL! Seriously god Bless you Brooke and keep up the great customer service & hosting.

Stunning Views of Back Bay & Seconds to the Beach
Great place for families walking distance from the beach. I’ll love to visit in the summer when we can enjoy the beach and everything Virginia Beach has to offer.

Historic Powhatan resort 2 bdrm
Colleen was a wonderful host and I would highly recommend this spot!
Family-friendly home rentals with Wifi

Cottage 2 Blocks to Virginia Beach Oceanfront -III
We had a wonderful stay here - perfectly appointed & had all the essentials for a quick getaway. Plenty of walkable coffee shops, and can’t beat the beach access. Jillian was super responsive & provided a great place for our weekend trip. Would definitely stay again!

2 BR Family & Pet Friendly House - Williamsburg
Charlene is a wonderful and very responsive host. This was our second time staying there when we visit Williamsburg. The location is great and only a few minutes from everything. The house was comfortable and had everything we needed to enjoy our week. We look forward to staying again in the future.

CLEAN Spacious Getaway near Beaches/Attractions+++
The place was centrally located. Clean, quiet and the perfect size. Very enjoyable stay.

Private apartment only 3 blocks from the Beach
We really enjoyed our long Easter weekend at Nataly’s 1st floor apartment in Virginia Beach! Great location:quiet,private,pretty backyard with nice deck,outside shower, and view of the water & lots of animal entertainment: Herons,Egrets,Mallards,fish,squirrels and 1 possum at night! 😆 The apartment is perfect for 2 people: Very Clean,comfy, & the Queen size Bed was very comfortable and the linens smelled so good! Loved the bathroom too! There’s so much to do, so many great places to eat at & funky bars & beer places to experience! Do yourself a favor and take a walk or rent bikes: You’re close enough to the beach-go enjoy it! We recommend “Rudee’s Tours”-The Dolphin Boat Cruise was AWESOME! We’ll be back! Danielle & Phil …2 Airbnb Superhosts from Pennsylvania !!!

Wil-O-Bay Getaway
Highly Recommend! My first time in Norfolk and I almost don’t want others to know about this place because it will be booked whenever I want to return. Peacefully neighbor and safe for women solo-traveler. The backyard is a dream and everything works great inside the home.

Lovely Ocean View Cottage
Very peaceful and fenced in yard was a plus for our small dog. The beach was only a couple of blocks away. House was clean and host was responsive.

An Entire House in Va Beach...just for two!
This house was a great get away, even thought it was a rental stay it felt like home and very peaceful. Great neighbors too.

Home away from home~Private,quiet, mins to bay
Loved our stay here. Great location, easy access & parking, private, quiet and comfortable. Jenn was very responsive and helpful. The kitchen was well stocked and we were able to cook and serve a St. Patrick's meal with no problems. We took a walk through the pretty neighborhood and visited several local restaurants nearby. Truly felt like it was a home away from home.
Family-friendly home rentals with a hot tub

Horses-Views-Dog Friendly-4WD Area
Thanks again for another relaxing stay at “Breakin’ Wind”! It’s been 5 years since our last trip here and we loved coming back to Terra’s place. We especially loved the hot tub, shelling and walks on the beach and seeing the horses again.

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!
We stayed a week at Kerri’s place in Virginia. She went above and beyond our expectations, very communicative and organized. She offered a ton of information and insights before and during our stay. Her place offers a delightful and relaxing getaway experience. The resort's picturesque location by the ocean provides stunning views and a serene atmosphere. The rooms are spacious, well-appointed, and comfortable, ensuring a pleasant stay. The resort amenities such as the pool, spa, and on-site restaurants add to the overall wonderful experience. The staff is friendly, accommodating, and dedicated to providing top-notch service to guests. Whether you're looking to relax by the beach or explore the nearby attractions, Boardwalk Resort is a fantastic choice for a vacation in Virginia. I would definitely recommend and revisit Kerri’s place.

Priv. pool, hot tub! Great location, walk to beach
Melissa‘s house is beautiful with a wonderful view of the sound. The kids enjoyed the pool even though it was still a bit chilly in April. (Just remember to take your own pool/beach towels!) We explored historic Corolla, the lighthouse, the wonderful bookstore, the beach and several Minigolf places by bike since the location was great for that. If you like cooking you will find that the kitchen has everything you need. Melissa was very responsive and helpful and did everything to make our stay great!

Marriott Manor Club Luxury Studio sleeps 4
10 minutes from everything to do. Great restaurants in the area. Quiet peaceful place. Hot tub and pool amenities were excellent.

Twin Suns at Beacon Villas w/ Indoor Pool!
This is our second time staying at the Beacon Villas. We love the location because it allows us to easily access the beach and all the amenities that Corolla Light Resort has to offer. The condo is the perfect size for our family - plenty of space and privacy when needed. It was very clean and looked exactly as described. When we return to Corolla, Beacon Villas will be first on our list of places to stay.

Croatan Beach - Big Kitchen, Hot Tub, 2 Masters
The home is gorgeous, and the neighborhood is serene and charming. Betsy made sure we settled in smoothly and had no trouble accessing the property. I highly recommend this place for a family beach vacation.

Williamsburg Vacation Villages Resort 2BR, 2BA
Nice condo, clean and quiet location. Lots of amenities. Glad we chose this place for our weekend visit to Williamsburg.

Walk to Beach 4BR | Pool | Hot Tub | Elevator
This was my first time renting someone’s home. One wow to the amazing homeowners for such a beautiful place my husband,m and children felt right at home. From the moment we pulled in, unpacked and biked to the beach our hearts were full! The decor is beautiful the upgrades they did really were breathtaking. We wish we were could have stayed another week it felt like home. Thank you to Vacasa and the homeowners. The only thing I would recommend is making sure the cleaner sweep, mop and vacuum. I did vacuum because there was sand, food and other things on the floor. But other than that perfection! Thank you again we hope to be able to stay there again.
Quick stats about vacation rentals that are family-friendly in Chesapeake
Total rentals
440 properties
Total number of reviews
14K reviews
Pet-friendly rentals
160 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
260 properties have a dedicated workspace
Wifi availability
430 properties include access to wifi
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- Ocean View Beach
- Sandbridge Beach
- North End Beaches
- Virginia Beach Oceanfront
- Carova Beach
- Chesapeake Beach
- Resort Beach
- Croatan Beach, Virginia
- Corolla Beach
- First Landing Beach
- Busch Gardens Williamsburg
- Bethel Beach
- Buckroe Beach
- Kingsmill Resort
- Currituck Beach Lighthouse
- Virginia Beach National Golf Club
- First Landing State Park
- Buckroe Beach and Park
- Water Country USA
- Golden Horseshoe Golf Club
- Grandview Beach
- Sarah Constant Beach Park
- Grove Beach
- Cape Charles Beachfront