
House holiday rentals in Chesapeake Beach
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Top-rated house rentals in Chesapeake Beach
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Popular amenities for house rentals in Chesapeake Beach
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!

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!

Country Comfort Close to the Beaches
I can't say enough positive things about Alice and her home. She was incredibly welcoming, and made my entire weekend a delight. Her home is beautiful, and it was a very comfortable stay. But Alice's kindness and generosity really went above and beyond. Thank you again!

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!

Sunrise, North End Beach
The best spot. Super nice amenities and very clean, great location, right across the street from beach access.
Weekly house rentals

The Canary Island … Keep Calm and Fish On
The property is spectacular. Everything about the accommodations was excellent. Not one complaint. Just praise. The host was very friendly and helpful. So were the neighbors!

The "Bison" contemporary retreat (King Bed)+
The place was beautiful inside and out. My family and I felt like we’re at home. I love the outdoor space. Most of the times, my parents and I chilled outside enjoying the weather and chitchatting with each other. My family and I came down from Pennsylvania to visit my sisters who live about 10-15 mins away from the home. My family and I had a great time during our weekend stay. Hopefully one day we’ll come back and stay at this beautiful home again. I highly recommend this beautiful home. Definitely 5 stars :)

Family-Friendly North End Stay w/ Bikes&Beach Gear
Tricia was responsive and very accommodating. It was a pleasure and a breeze to stay at her space. It was clean and stocked with all baby amenities like toys crib and highchair. It was close to the beach and to many attractions.

*Semi-Priv Beach*King Bed* Waterfront*EV Charger
Home is very clean, comfortable & beautifully decorated. Surprisingly it is equipped with extras like paper towels, toilet paper, trash bags, detergent, coffee & water. The Host goes the extra mile they have made this a beautiful home away from home! I highly recommend this property, you won’t regret it.

Last Resort,family friendly,child care available
Rented the Airbnb for me and my daughter for Father’s Day weekend. We felt comfortable and right at home. The reservation of peace and comfort was very much appreciated. The host, “Jaimee” was very professional, kind and attentive to any needs upon request. She checked in to see how the check-in process was which was easy and simple. In addition, she checked in to see how well our stay was going which was very much appreciative. She didn’t have to, but the fact that she took the time and initiative was beyond thoughtful. I would absolutely recommend this piece of comfort and peace to anyone and would definitely look to rent again in the near future. Thank you for welcoming your home to me and mine and the extension of care and hospitality.

Anne's Beachfront Shangri-La
We had a wonderful stay at Brandon’s place! It was private and beautiful! The house also contained everything we could possibly need from kayaks to a pack and play! We will definitely be back! Thank you!

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.
Far enough away from the busiest sections but close enough to get to where we needed in a short amount of time. Only one suggestion....maybe some lamps in the bedrooms. It was SUPER clean and Criska was AMAZING
Private house rentals

R & R River House
Overall this was a great experience, & even with the max amount of guests (6 total) we generally had a lot of space; places to sit & relax; & all felt very comfortable. The view of the lake was also incredible & the amenities provided were top notch. The only criticism I would give is that the listing seems a little misleading about the building being a standalone house vs the town home/condo style house that it actually is. This wasn’t a huge issue but it seems fair to note as the parking was a little confusing once we realized that it was a town house with a parking lot, rather than a standalone one with a driveway. To be fair we did have the max amount of guests & according to Jason this was out of the norm; & Jason did do his best to communicate in finding places to park- but I feel that if there’s any hesitation he might have of that many people being there then the listing may need to be made more clear. Overall though we had a great time & enjoyed the view most of all.

Family Getaway | 1 Block from Beach | Game Room
We had a wonderful stay this past weekend at Brian’s place. We were in town for a wedding and enjoyed some down time at the house playing air hockey, having a meal together at the large dining table and walking our dogs on the beach (a very short walk away). The dogs each had their own dog bed and the fenced in yard was a plus! Check in/out was seamless and Brian was very responsive with recommendations and answering any questions that we had. The house was very clean and comfortable and provided the perfect space for our family to make new memories.

Waterfront/Arcade/Fishing Fun
home away from home but with vacation vibes . my family enjoyed. we will definitely rent here again when in VA :) we made amazing memories and bonded as a family well needed..

York River | Chesapeake Bay Bliss: Fishing Retreat
Our family of four loved staying here. Our 10-year-old delighted in crabbing and playing board games (chess and Battleship). Our 7-year-old desperately wanted to splash around the York River even though it was freezing in April. The local recommendations were much appreciated and the impact of staring at a horizon line cannot be overestimated.

Charming Home by the Sea, a block from the beach!
Love, love love this place and the location! Short walk to the beach! A few wonderful restaurants near. The house was perfect and super clean. Karen was the perfect host- responsive, kind while giving complete privacy. Thank you for an amazing week!!!

Modern 4br beach house - Norfolk
Beautiful home close to the beach with walkable restaurants/ coffee shops/ brewery/ farmers market/ Chesapeake bay. We particularly preferred the bay for calmer waters as we have young children. Beautiful spacious home. Huge fenced in yard. Convenient side spigot for rinsing fear post beach. Helpful responsive hosts. Thanks for having us!!

*NEW* Spacious/Standalone 4BR Beach House
Absolutely loved our stay at this beautiful beach home! The space was spotless, stylish, and incredibly comfortable — perfect for our group. Each room felt thoughtfully designed, and we had more than enough space to relax and enjoy. The kitchen was fully stocked, the beds were cozy, and the balcony was the perfect morning hangout spot. The 10-minute walk to the beach was a breeze, and we appreciated the quiet, charming neighborhood. It truly felt like a home away from home. Staton was a fantastic host — responsive, helpful, and clearly dedicated to creating a great guest experience. This house was everything we hoped for and more. We’ll absolutely be back!

In the Heart of Virginia Beach perfect for groups!
Great for families. Great location. Clean. Spacious. Did not disappoint. I will come back again.
Destinations to explore
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- Chesapeake Bay
- 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