Holiday Homes in Chesapeake

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Featured Holiday Homes in Chesapeake and around

Our top choices for Chesapeake holiday homes

"The house is great, easy to host and feed a group, 4 blocks to beach, nice outdoor deck, beds were good for sleeping."

"The house was big and plenty of room for a big family. Very well stocked and very convenient location. "

"Great place, very clean, plenty of room for a large family.Location was good and property & view of the water were very nice. Easy to get to and many restaurants and stores nearby. Highly recommend this place for your next visit. "

"The stay was perfect for our needs, close to the beach and as described. "

includes taxes & fees

30 Sept - 1 Oct

"Nice size for a family of 7. But the property needs upgrades. It has been well used over the years."

"Beach Baby Bingo place is nice, neat, and comfortable. It is near the places (15 to 17 minutes drive )where we would like to visit in VA Beach like the VA aquarium and VA Beach front plus it is also nearby an Asian store. "

includes taxes & fees

3 Oct - 4 Oct

"We loved the house, the locations and the beach!!!"

"This large house was perfect for our big family gathering. We loved the huge dining table, and the 2 kitchen areas were great for meal prep. There was plenty of dishes, utensils, and food storage spaces. We noticed that some furnishings had been nicely updated since the online photos. We enjoyed the beach, just a short walk from the house. The indoor pool, hot tub, & pool table kept our group entertained in the evenings. Location is just a short drive from the VA Beach boardwalk for those who...

"We enjoyed our stay! The Beach and location was close enough to take the Dolphin boat tour and walk to restaurants. The only thing that would have been good was cleaning products to clean the tub. "

"Very nice house in a cool spot. Enjoyedthe games. Horses everywhere. "

Beach nearby, sun-loungers, beach towels

"We had a wonderful time, Kevin was a great host reaching out to use several times to make our trip Great, Beautiful property, Horses pass through the property yard daily Thanks, Will book again if we are in the area"

"The house was clean, plenty of room to relax. Beds are comfortable, quiet neighborhood. "

"This home was perfect for our group that was visiting for a friend’s retirement. There was only six of us, and this property gave us the ability to comfortably stay without feeling cramped in any way. A great alternative to staying in a hotel that wouldn’t have provided community space, patio/grotto, kitchen, laundry, garage, etc. and would have cost each of us about the same, or more, than splitting the cost of this clean and spacious location. None of us were familiar with the area but the...

includes taxes & fees

23 Sept - 24 Sept

3 bedrooms, iron/ironing board, free WiFi, bed sheets

"The property was A — just as described! It was super close to the beach and restaurants, making it the perfect location. We really enjoyed our stay, and it was ideal for my large family. Would definitely stay again!"

Smart TV, fireplace, video games, DVD player

"This house was perfect for my family. The location was beautiful "

"Beautiful home!!! Very well kept and clean. The location was everything you can dream of! Wild horses seen daily, gorgeous beach, great pool!!! Thank you for sharing your home with us!"

"Great place to stay with family. Was very clean and well kept. We didn't have much sunshine, but we had a great stay! Host was great and house was like advertised."