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Family-friendly vacation rentals in Chesapeake

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Chesapeake family-friendly rentals

Family-friendly home rentals with a pool

Superhost
Townhouse in Williamsburg
4.84 out of 5 average rating, 80 reviews

Williamsburg Vacation Villages 4BR, 4BA

KristenRating, 5 stars1 week ago
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!
Guest favorite
Apartment in Williamsburg
4.86 out of 5 average rating, 21 reviews

*Historic Powhatan Resort- 2 bedroom

HaleyRating, 5 stars16 months ago
It was a perfect little get away, while learning colonial history! Definitely recommend coming back when it is warmer out!
Guest favorite
Apartment in Williamsburg
4.85 out of 5 average rating, 169 reviews

Westgate Historic Williamsburg One Bedroom

JordanRating, 5 stars1 month ago
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!
Top guest favorite
Home in Sandbridge
4.99 out of 5 average rating, 81 reviews

Breathtaking Ocean views at Pinch Me, 8bdrm, 6bath

NicholasRating, 5 stars3 weeks ago
Beautiful home in a wonderful location. Tanya was very friendly and communicative throughout the process.
Guest favorite
Guesthouse in Virginia Beach
4.72 out of 5 average rating, 115 reviews

POOL, Pool House, Hot Tub, Grill, 2 bedroom

John DavidRating, 5 stars4 weeks ago
He was so nice and everything!!
Superhost
Condo in Williamsburg
4.78 out of 5 average rating, 9 reviews

Timeshare Kingsgate Resort- 2 bdrm

KemRating, 5 stars21 months ago
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.
Superhost
Home in Sandbridge
4.84 out of 5 average rating, 125 reviews

Stunning Views of Back Bay & Seconds to the Beach

SigridRating, 5 stars1 month ago
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.
Guest favorite
Condo in Williamsburg
4.78 out of 5 average rating, 9 reviews

Historic Powhatan resort 2 bdrm

JasonRating, 5 stars5 months ago
Colleen was a wonderful host and I would highly recommend this spot!

Family-friendly home rentals with Wifi

Superhost
Home in Virginia Beach
4.72 out of 5 average rating, 347 reviews

Cottage 2 Blocks to Virginia Beach Oceanfront -III

HankRating, 5 stars1 month ago
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!
Guest favorite
Home in Williamsburg
4.84 out of 5 average rating, 80 reviews

2 BR Family & Pet Friendly House - Williamsburg

DavidRating, 5 stars8 months ago
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.
Superhost
Condo in Hampton
4.68 out of 5 average rating, 665 reviews

CLEAN Spacious Getaway near Beaches/Attractions+++

BeverlyRating, 5 stars1 week ago
The place was centrally located. Clean, quiet and the perfect size. Very enjoyable stay.
Guest favorite
Apartment in Virginia Beach
4.91 out of 5 average rating, 529 reviews

Private apartment only 3 blocks from the Beach

DanielleRating, 5 stars1 week ago
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 !!!
Superhost
Home in Norfolk
4.78 out of 5 average rating, 36 reviews

Wil-O-Bay Getaway

TarshaRating, 5 stars10 months ago
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.
Top guest favorite
Cottage in Norfolk
4.97 out of 5 average rating, 325 reviews

Lovely Ocean View Cottage

ShellyRating, 5 stars1 week ago
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.
Guest favorite
Home in Virginia Beach
4.84 out of 5 average rating, 64 reviews

An Entire House in Va Beach...just for two!

DwayneRating, 5 stars4 weeks ago
This house was a great get away, even thought it was a rental stay it felt like home and very peaceful. Great neighbors too.
Top guest favorite
Guest suite in Virginia Beach
4.98 out of 5 average rating, 300 reviews

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

JimRating, 5 stars1 month ago
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

Guest favorite
Cottage in Corolla
4.88 out of 5 average rating, 146 reviews

Horses-Views-Dog Friendly-4WD Area

MaggieRating, 5 stars3 weeks ago
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.
Superhost
Condo in Virginia Beach
5 out of 5 average rating, 4 reviews

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!

AldoRating, 5 stars9 months ago
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.
Home in Corolla
4.69 out of 5 average rating, 117 reviews

Priv. pool, hot tub! Great location, walk to beach

IngaRating, 5 stars1 week ago
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!
Guest favorite
Condo in Williamsburg
4.84 out of 5 average rating, 19 reviews

Marriott Manor Club Luxury Studio sleeps 4

LucasRating, 5 stars4 months ago
10 minutes from everything to do. Great restaurants in the area. Quiet peaceful place. Hot tub and pool amenities were excellent.
Townhouse in Corolla
4.63 out of 5 average rating, 16 reviews

Twin Suns at Beacon Villas w/ Indoor Pool!

CaraRating, 5 stars10 months ago
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.
Superhost
Home in Virginia Beach
4.65 out of 5 average rating, 128 reviews

Croatan Beach - Big Kitchen, Hot Tub, 2 Masters

SharonRating, 5 stars2 months ago
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.
Superhost
Condo in Williamsburg
4.83 out of 5 average rating, 23 reviews

Williamsburg Vacation Villages Resort 2BR, 2BA

JamesRating, 5 stars6 months ago
Nice condo, clean and quiet location. Lots of amenities. Glad we chose this place for our weekend visit to Williamsburg.
Home in Corolla
4.73 out of 5 average rating, 22 reviews

Walk to Beach 4BR | Pool | Hot Tub | Elevator

JessicaRating, 5 stars9 months ago
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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