
House holiday rentals in Chesapeake
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Top-rated house rentals in Chesapeake
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Popular amenities for house rentals in Chesapeake
House rentals with a pool

THE OLD BEACON 1 | Beach Living
Beautiful home within walking distance to everything you need, especially the beach and restaurants. Clean home with cozy feel. My son never wanted to leave the beautiful pool at the property. Would recommended to families!!

York River Vacation Home
We had a wonderful stay here! Everything was exactly as described. Eugene was really responsive when communicating and super friendly! I would highly recommend staying here if you get the chance. Thank you again for such a relaxing place to stay!

The Blue Octopus~Private Pool~HotTub~Beach~FirePit
Family vacation for almost a week and everyone loved it! We definitely recommend families to come to the Blue Octopus for their next visit to Ocean View-Willoughby Spit. Friendly, clean and with all the amenities for the whole family.

Paint The Beach Pink! Full House | Private Pool
Check in was super easy, the AC was on when we arrived which was great after a long Uber. The pool felt nice and the whole backyard area was fantastic. We ended up using the bikes a lot more than we thought which was a lot of fun. It's a quick bike ride to the boardwalk and walking didn't take too much longer. Bradley was very quick to respond whenever I had a question about anything. If we come back to Virginia Beach we will definitely be checking the availability of this house!

Gorgeous Vacation House
The house was super clean when we got there, the temperature of the house was great the entire stay. The pool was certainly clean, but since we went early, June the water was a little bit cold, but it felt really nice and refreshing honestly. There were three beach chairs and a wagon there that were helpful for traveling to the beach. There were available cups plate, utensils, and all the necessities that you would need, they even had shampoo and conditioner bottles there for us. We weren’t aware that there was a code to get into the house so instructions for check-in were a little bit unclear, but all I had to do is message and they responded. Overall, I would recommend staying here because even though the area surrounding isn’t the nicest, I felt safe the entire time at that house!

Stunning Views of Back Bay & Seconds to the Beach
Great location and host. The home was the perfect size for my family and friends.

Perfect Getaway!
We had a great family visit at this house. We really enjoyed the pool and whole house was very comfortable and clean! It was nice to just hang all day by the pool or top for a sanctuary from a long day of events. Sabrina was very attentive and responsive with questions and situations, appreciate her flexibility as a host!

Salida del Sol, North End Beach
Mark is a great host. The house is immaculate. Every little detail is perfect. By far the nicest AirBNB I have ever rented. Mark made sure everything was perfect for our visit with our son in the Navy.
Weekly house rentals

Private Beachfront Modern Villa: Outdoor Shower!
This was our second stay at this Airbnb and we were incredibly glad we decided to book again! The place is exactly as described, has all the beach supplies so you don’t need to pack it all, is just a quick walk to beach (awesome with kids), and the view can’t be beat. Heidi was an extremely responsive host who went above and beyond to make sure our stay was fantastic - you can tell her priority is the guest! My family of 5 plus a grandma enjoyed lazy mornings on the patio, taking in stunning sunsets over dinner, and long days on the beach (bathroom breaks back at the house are a snap due to the close proximity). The outdoor shower with warm water is especially helpful with kids! We will be back at least twice this upcoming year. Thanks for another great stay!

941 Coastal Luxury Retreat
It was a great place to stay! Super clean and comfortable. Many great places with if walking distances or a short drive. The farmer’s market is a must do! Carrie was super helpful with a question during the stay. We would stay again!

Convenient Location!
We have just returned home from Deborah’s place and let me just say, after arriving and walking through the home I could feel the warmth and love poured into this home. It was welcoming and peaceful and awww, before long we were home. Deborah thought of everything to ensure the home is comfortable. This home literally has everything we needed for our entire stay. Such a nice touch! The kitchen had everything, and everything worked flawlessly. Deborah, your attention to detail is a gift! My family and I thoroughly enjoyed your home, and are definitely look forward to returning when next we visit Va Beach. Thank you for opening up your childhood home to us. We thought of your family as we moved around the home. See you soon!

Home Away From Home
Place was as described and all info was given and easy to understand definitely worth staying if your in that area

Cozy Retreat
It's was a lovely place

Tiny House Near Beach & Naval Base - Privacy Fence
This tiny home was just the right size. My dogs loved the fenced in yard and my husband and I enjoyed the quiet location. Just close enough to the beach and restaurants. I would definitely consider going back!

Backyard Bungalow | Near Beach
The house was spotless, cozy, and exactly what we needed for a relaxing stay. We felt right at home and truly enjoyed every moment. We’d definitely love to return!

Quiet & Private, Comfy Beds, Fire Pit, & Bikes
Had a great girls weekend. It was peaceful and such a cute and quiet neighborhood. We would stay again. It’s located close to everything. The hot water was wonderful. 🤭
Private house rentals

Hearts Blossom By the Sea
Hearts Blossom by the Sea was absolutely adorable and very clean. The space provided everything we needed. Our hosts were kind and attentive, and the walking distance from Hearts Blossom to the beach is truly amazing. We didn't want to leave!

10 min to Ocean View: BBQ | Volleyball| Fire Pit
Very nice stay, very nice home and neighborhood. Ideal for a “base camp” to explore all of eastern Virginia and neighboring areas. Sometimes, traveling in this manner, small glitches happen. Most are easily solved with good communication, a responsive host and mutual cooperation. Had a small glitch - easily and quickly solved with these practices. Many thanks to the Host of this property!

The Pines- Family Entertainment Room
This place was everything it is advertised to be. It was the perfect fit for my family of 7. The game room was a great addition for the kids!

The Bartlett Inn
Stayed here was a family event it was spacious with a well equipped kitchen . The neighborhood was very quiet and safe could walk for miles without seeing a car or busy street .

Coastal Comfort: 2BR Retreat near Beaches/King Bed
We had a great stay at Ali’s place! It was very clean and the beds were so comfortable! The location is wonderful and near shopping, restaurants, and Buckroe Beach is just minutes away. I would highly recommend and will stay again when back in town!

Elegance Escape on Saunders Dr
My family and I absolutely love our "Home away from home." This was our 2nd year enjoying all of the elegance and fun your home has to offer. Giovanni and family are the best host's that we have ever had. Communication is so important, and any time I reached out, I was quickly responded to. We got into town a little early, and they were very accommodating when they didn't have to be. The home is immaculate and warm and we didn't have to leave to be entertained. Visiting my son, who is active duty military is even more amazing when you have such a beautiful home with plenty of family things to do right at your fingertips. The neighborhood is peaceful and we felt safe and secure in our own private oasis! Thanks so much for making our stay just as amazing as the 1st time. Looking forward to our next trip!!

Charming Home by the Sea, a block from the beach!
Lovely house, super clean, everything we needed. Only a short walk to the beach, quiet neighbors. Would recommend!

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!
This home stands out among the many air B&B’s I have stayed it. Emily and Abel provided many extras such as cold water and snacks when we arrived, beach towels for our use, dog food bowls for our dog, soft beds with plush throws to use at our leisure. The neighborhood is walkable filled with southern charm. Our family used this home as a gathering place for my son’s wedding. It exceeded my expectations.
Quick stats about house rentals in Chesapeake
Total rentals
560 properties
Total number of reviews
13K reviews
Family-friendly rentals
280 properties are a good fit for families
Pet-friendly rentals
150 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
310 properties have a dedicated workspace
Destinations to explore
- Virginia Beach Holiday rentals
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- First Landing State Park
- Water Country USA
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Currituck Beach Lighthouse
- Outlook Beach
- Jamestown Settlement
- Haven Beach
- Ocean Breeze Waterpark
- Sarah Constant Beach Park
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Kiptopeke Beach
- Golden Horseshoe Golf Club