Family-friendly holiday rentals in Chesapeake Beach

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Chesapeake Beach family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Condo in Williamsburg
5 out of 5 average rating, 3 reviews

The Historic Powhatan Resort 1BD

StacyRating, 5 stars34 months ago
This was an amazing place! We loved the clean, comfortable rooms, the service was great, the pool and mini golf were so fun! And location- perfect!!
Superhost
Condo in Virginia Beach
5 out of 5 average rating, 4 reviews

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

AldoRating, 5 stars10 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.
Guest favourite
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!
Superhost
Condo in Williamsburg
4.73 out of 5 average rating, 26 reviews

Wyndham Governors Green Resort- 2 bdrm -2 nt min

RosemaryRating, 5 stars4 months ago
Great place in a great location. We loved having our own space with two bedrooms and a full kitchen only a short drive from Colonial Williamsburg.
Guest favourite
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.
Guest favourite
Home in Virginia Beach
4.74 out of 5 average rating, 87 reviews

7+ Bdrm, 5.5 Bath Pool/Hot Tub Sandbridge Beach VA

DaniseRating, 5 stars7 months ago
Owner very responsive and easy to communicate with. Great location
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.

Family- and pet-friendly home rentals

Guest favourite
Home in Virginia Beach
4.96 out of 5 average rating, 131 reviews

Water Oaks at Chic's Beach

NewRating, 5 stars1 week ago
We stayed here over spring break with our young kids. Tommy and Janet were very friendly and responsive. The location is great! Literally right across the street from the beach, and close to our all time favorite brewery :) we'd love to come back again in the summer months!
Guest favourite
Cottage in Corolla
4.88 out of 5 average rating, 147 reviews

Horses-Views-Dog Friendly-4WD Area

StacyRating, 5 stars2 weeks ago
Enjoyed every minute of our stay! The dogs loved the location and driving on the beach was a lot of fun. 2 stallions walked through the dunes directly off the porch. The house was cozy and all we needed!
Guest favourite
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!
Guest favourite
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.
Guest favourite
Guest suite in Virginia Beach
4.9 out of 5 average rating, 629 reviews

Quiet Neighborhood 7 Miles From the Beaches

CeceliaRating, 5 stars1 week ago
Mona is a sweetheart, and her place was perfect for my dog and me. It was clean and had the cutest backyard. Will definitely book again with her if I’m back in Virginia Beach
Guest favourite
Barn in Virginia Beach
4.8 out of 5 average rating, 909 reviews

Cozy craftsman barn near the bay!

DebRating, 5 stars2 weeks ago
We loved our stay in the barn! My husband was a little skeptical when we first say it from the outside, but the inside was just as described and completely adorable. We also greatly appreciated rhe complimentary water and snacks. The beds (that includes the pullout couch) were very comfortable. The bathroom was clean (looked like it had been redone somewhat recently?), and with 3 people showering we didn’t run out of hot water or anything! There were instructions for everything, and there are coffee shops and lots of stores a very short drive away.
Top Guest favourite
Cottage in Norfolk
4.97 out of 5 average rating, 326 reviews

Lovely Ocean View Cottage

MargoRating, 5 stars2 days ago
We had a wonderful stay with our puppy! Chuck was very thoughtful and welcoming with the many amenities available. We felt right at home and it's so close to restaurants and the water. Looking forward to our next visit!
Top Guest favourite
Home in Williamsburg
4.97 out of 5 average rating, 220 reviews

Casita on the Corner

KathrynRating, 5 stars3 weeks ago
We had a great stay! The house was clean ans quiet, and the kitchen had all of the essentials you would need (spices, condiments, etc.). The house is close to all of the major attractions/downtown Williamsburg! The deck and fenced-in backyard were perfect for our toddler and pup!

Family-friendly home rentals with a pool

Home in Cape Charles
4.77 out of 5 average rating, 78 reviews

Family Retreat, In-Ground Pool, plus Private Beach

AndrewRating, 5 stars8 months ago
This house and stay were exactly what we needed! We are a quiet family that loves peaceful spaces. The home was beautiful, well maintained, clean, updated, and extremely well appointed. Access to both the beach and lake was easy, as was getting into and out of town. Jack proactively reached out to us when we got there to ensure everything was in order and offered assistance if we needed anything. We didn’t need anything during the week but we felt good knowing he was available. We met some of the neighbors in passing and they were friendly and welcoming, too. Wonderful experience!
Top Guest favourite
Home in Virginia Beach
4.99 out of 5 average rating, 82 reviews

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

SamanthaRating, 5 stars2 days ago
Beautiful place, such a great view of the beach. Beach access right across the street. Loved it. Spacious area, lots of room.
Superhost
Home in Virginia Beach
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.
Condo in Williamsburg
4.8 out of 5 average rating, 10 reviews

2BDR/2BA in the historic city of Williamsburg, VA

ClaireRating, 5 stars4 months ago
Our place was very clean, the stay was private and in a nice location. Debbie was very helpful and responsive
Apartment in Virginia Beach
4.78 out of 5 average rating, 102 reviews

Virginia Beach Condo

RogerRating, 5 stars20 months ago
The location was great. Two streets walk to the boardwalk and two streets over to Neptune Statue on 30th Street. Supermarket for groceries was across the street from condo. The washer and dryer and dishwasher made everything so easy to keep up with. Keyless entry is perfect. There are many fun things to do in the area that is either a short walk or short drive. Examples are iFly indoor skydiving, parasailing, kayaking with dolphins, riding bikes/skateboards, mini-golf, etc. We had a great time!
Condo in Williamsburg
4.75 out of 5 average rating, 4 reviews

2 Bedroom Condo at Greensprings Vacation Resort

Lesly AnneRating, 5 stars32 months ago
When our first reservation fell through, Nadine quickly helped us secure a place for our family of six and was incredibly responsive to all our needs. Our unit was perfect for us — much bigger than I expected for a two bedroom, and the pools were also a big hit. Location is central to Williamsburg sights.
Superhost
Cabin in Williamsburg
4.68 out of 5 average rating, 59 reviews

Pet Friendly Deluxe Cabin in Williamsburg, VA

NataliaRating, 5 stars8 months ago
My husband and I along with our 2 dogs had great weekend stay at the Williamsburg campground. The cabin was just very clean and comfortable with all we needed for the weekend. The campground itself was wonderful with plenty of things to do, although we were there to explore Williamsburg and surrounding areas. overall a great stay and would definitely return again!!
Apartment in Virginia Beach
4.8 out of 5 average rating, 5 reviews

Luxury Beach Front Apartment

DanRating, 5 stars23 months ago
Jenna is a great host. Very responsive, personable throughout the process. Location is great. Right in the beach. Several restaurants are walkable. Beach here has a playground for the kids and a work out set up for those inclined. Pools and spa were great, especially on bad weather days.

Destinations to explore