Holiday Homes in Chesapeake

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Featured Holiday Homes in Chesapeake and around

Relax in this serene bedroom with a large bed and high ceiling, featuring a sliding door and air conditioning unit.

"This place is very nice, very clean, modern, private. "

Enjoy a meal with a view at this oceanfront restaurant, overlooking the pier and beach.

"Like the fire pit outside and so close to the beach and the pier the only downside is 1 bedroom doesn’t have AC but other than that it’s perfect We’ll stay there again "

includes taxes & fees

12 Aug - 13 Aug

Kitchen features a spacious cabinet with two open shelves for storing a variety of dishes.

"I stayed here for my birthday to hang out with friends and we loved it. The host was super sweet and very accommodating. Even let us stay later and check in early."

includes taxes & fees

23 Aug - 24 Aug

Enter a serene space with a view of the outdoors from the window, featuring a comfortable rocking chair and a small table with a plant.

"We enjoyed 4 days and 3 nights at this cute home. The house was just perfect for our family and we throughly enjoyed the porch and back yard which is where we spent most of our time. The house had everything we needed and more. The walk down to the beach was beautiful and it felt like we had our own private beach. If you are looking to get away from the hustle and bustle this is a great place. Neighbors are close in proximity, but we never really saw anyone and it was all quiet. We did meet one...

Relax in a serene backyard oasis with a potted plant and two comfortable chairs.

"Loved the stay! Property was very clean, quiet and easy to get to everything Virginia Beach has to offer. The property manager was very quick to respond and helpful. Will stay there again"

includes taxes & fees

6 Aug - 7 Aug

Walk along the pier to the Ocean View Fishing Pier building, offering stunning ocean views.

"Great little place! Clean, safe, & has everything you need for a weekend getaway! "

Relax on the deck with ocean views and comfortable seating.

"The owner is easily accessible and they maintain a fantastic property true to its listing. My teenagers loved the property and our stay."

Enjoy cooking in this well-lit kitchen with a refrigerator, dishwasher, and large window offering a view.

"We thoroughly enjoyed 3-day Independence Day holiday on Sandbridge Beach. The check-in process was effortless and Roger was very prompt in answering questions before and throughout our stay. We really loved this home because it offered so much of what we wanted to do on vacation including a large swimming pool, hot tub, and boat/kayak access on the canal. The beach was a short walk out of the neighborhood and across the street to the quiet Sandbridge Beach. We liked the home and location so...

Walk along the Ocean View Fishing Pier, taking in the serene views of the surrounding waters.

"Great stay "

includes taxes & fees

6 Aug - 7 Aug

Experience the charm of this multi-level building with a spacious upper deck and balconies.

"We stayed as a family for our spring break. House was clean, beds were comfortable, and location was great! The kids loved seeing wild horses right off the deck and we found more by driving around. We spent one day on the beach and that was a lot of fun. Weather was a bit chilly, but nothing we could control!"

Walk along the beach to the ocean's edge, where waves gently approach the shore.

"Me and my family had a wonderful time staying here on Carova Beach. This place was clean and ready to go for visitors and had everything needed to enjoy a nice secluded stay on the beach! Thanks!"

Relax on the deck with comfortable wicker furniture and enjoy the serene surroundings.

includes taxes & fees

28 Aug - 29 Aug

Relax on the covered porch with a sofa, chairs, and a table, taking in the view from the large window.

"Our recent stay was great. The property was exactly as described—clean and comfortable, everything we needed for a relaxing getaway. The location was perfect."

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and microwave.

"Great location, clean & everything we needed was here. We would definately come back"

Enjoy cooking in this well-lit kitchen with a central island, refrigerator, and stove.

"We arrived at the 4 pm check-in time to a house that was not cleaned following the previous guests stay. Even the toilet was clogged. Management company called Brindley Beach said the cleaning company truck broke down but nobody called to let us know. We had to wait into the night for the house to be cleaned. They also said the horse manure at the front door was not their problem. Great house but the management company was terrible! "

Relax in this stylish living room with a sofa, armchair, and coffee table, offering a view of the ocean and beach.

"Amazing house, great location! This house was perfect for our family vacation. The wild horses strolled by a few times and the owner was great on giving helpful tips on where to find the horses. Highly suggest this house if you want to have a once in a lifetime experience in the Outer Banks! "

Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and sink.

"First want to start off by saying the house is as described actually better then the photos online led us to believe. It's an older house but was clean and decorated beautifully. For the money, description, and space you get staying in this home I would definatley recomend you staying here. It's not a 5 star luxury resort, but I gave 5 stars for the house being it was better then what we expected. Our family enjoyed our stay."

includes taxes & fees

3 Aug - 4 Aug