
Condo vacation rentals in Chesapeake
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Top-rated condo rentals in Chesapeake
Guests agree: these condos are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chesapeake condo rentals
Weekly condo rentals

Sandbridge Beach - DeepSeaSide Retreat
The perfect hosts!! Best stocked house we have ever stayed in. Already planning our trip next year!!

The Port - Large condo on Mason Avenue!
Wow. What a stunning place with high ceilings, beautiful decor, lots of windows, a great roof deck, and a fabulous location in the center of the historic business district.

Good Vibes at the Beach
Colin is an impeccable host! He’s caring-he’s honest- he answers all concerns immediately- His “home” is one of the nicest beautifully decorated homes we have stayed in-and so clean!!! Thank you for the privilege of staying at your place

21st Street Condo - 1 block from the Dome
Highly Recommended. Everything we needed for a great stay. Comfortable king-size bed; well stocked and very clean; just blocks from the beach and fun!!! Responsive communications and well-laid-out instructions for ease of stay. Given the opportunity, we will book again.

Marriott's Manor Club Ford's Colony 2BD Villa Slee
The villa was the perfect place for our family to stay for graduation weekend at William and Mary. Plenty of space and very comfortable. Setting was lovely and great for walks in our down time. The only issue we had was the villa was not ready at the designated check in time and we had to wait an hour before we could get in.

1 Bdrm Condo in Williamsburg, VA
We really loved our time at Wyndham Kingsgate. The rooms have been recently updated and the amenities were great for kids. Super convenient location next to tons of restaurants and just a short drive to colonial Williamsburg or Busch gardens. Our girls slept on the pullout sofa bed which was comfortable as sofa beds go! Elizabeth was responsive and helpful! We look forward to staying here again.

Chic's Beach Rental and Fishing
i am very familiar with this area and of course the beach we always go to is 10 steps away from this airbnb! it is so clean inside and spacious, clear check in, beautiful backyard space with a large deck and the grill and surfboards! i think the best part is that the tv comes with disney plus and hulu and all the streaming services, so we are able to watch all of our shows from at home! the host, mike, was very friendly and i talked to him for a short while at sunrise. he’s very nice and a great host, he offered checking in earlier and checking out late because there was nobody else booked! so happy with this whole experience and the house fit my whole family with a couple guests too! i want to be selfish and say don’t book, but for the best experience, you need to book here!

2 Bedroom Stylish Kingsmill condo
We’ve stayed here several times when visiting the park. Extremely close, quiet, and secure. We greatly recommend for anyone wanting the same!
Pet-friendly condo rentals

Cozy & Fun Hampton Condo ~ WIFI & W/D!
He had a great time

Beachfront Getaway, Pet Friendly, Mermaid Suite
What an amazing stay! I've never been satisfied with an Airbnb, the photos always are so much nicer than the reality - but Big Blue was actually even better than advertised! Merlyn's communication prior to arrival made things very easy. Accessing the unit was simple, and I felt safe with the self-locking doors. The unit was clean and so comfortable, with many personal touches - I instantly felt at home. I was overjoyed when I arrived and toured the unit. Really exceeded my expectations which was such a different feeling than all the other Airbnb I've rented over the years. The beach access was tidy and pretty, the gym and beach gear a nice touch, and the foot wash station was appreciated after my morning walks with the dog. I really can't say enough great things about my stay here. Hosts were friendly and helpful every step of the way. We mostly spent our time traveling around the area from VA Beach to OBX so I can't speak much about Norfolk/Ocean View. I would def rent Big Blue again.

August Suite | Beach | Balcony | Fire Pit
loved our stay. cozy home with everything you need and FANTASTIC host who meets all yours demands without hesitation.

Ocean Bliss: Cozy Apt Retreat(D)
The house is in an amazing location with lots to do and the host is very communicative and helpful.

Enjoy Sea Life! Steps to the Beach!
Lynn's place was comfortable, convenient, and clean. We appreciated how stocked and organized the home was as well. It was an easy walk to the beach. We were spending time with family staying at Corolla Light and this was a very convenient spot to do so.

*New*OceansideCondo PetsOK Pool GameRoom No Stairs
We had a wonderful time! Lisa was extremely communicative and responsive. The condo was clean and very comfortable. Location was perfect - close to shops and an easy 10 minute walk to the beach. The beach cart that was provided was very helpful and made the walk to the beach a breeze…. The pool was very nice too. Look forward to coming back soon.

Wonderful & tranquil beach retreat: 2BR/2BA Condo.
Over the moon about this place! Felt like home away from and with two kids under two it was so easy! So grateful for the wonderful stay ! 100% coming back for a longer stay!

Walk to Corolla Village and the Beach!
We really enjoyed our stay and the location was perfect for walking to the beach, park and the shops in Corolla village. The kitchen was nicely stocked for our cooking needs but we also enjoyed having lots of walkable food and coffee options close by. Having the pool was nice treat as well!
Condo rentals with a pool

New Beachside Villa: Steps to Sand, Dog-Friendly!
We had a great stay! Highly recommend this spot for families- lots of very convenient amenities and a really nice community super close to the beach.

OceanSands 1BR Free AquariumBikesChairs Oceanfront
Anthony was a great host. Very communicative and answered any questions, I had. The home is as described. A nice little hidden gem, right off the beach front. 10/10. Will definitely return.

Oyster & Pearl Beautiful New Single Level Condo
Our stay was wonderful! We were steps away from the beach and were provided a wagon to haul the chairs, umbrellas and cooler to the beach. Everything was clean and looked exactly like the photos. Great location to get to the wild horse tour and many restaurants within a 30 minute drive. Lynn always responded immediately with clear directions. Thank you

Coastal Beach condo-amazing view and indoor pool
An amazing place in the quieter area of Virginia Beach. We will be back!

Sea La Vie at The Beach Club - Walk to Beach
Beautiful home and very spacious. Lynn was very helpful and came very late at night to help us with a lock box issue. Very close to the beach and had lots of beach items provided

Sunny 2BR 1st-Floor | Balcony | Pool
Very Beautiful condo! It is a little distance from most restaurants/stores and doordash in not available in the area, but it’s a beautiful spot to relax and recharge. Beds were comfortable and kitchen was fully equipped to cook in. We will be returning!!

Bay Creek Blessed at The Fairways
Book this condo! It was the cleanest AirBnB I’ve ever rented but was still warm and comfortable. You can tell the condo is well taken care of. The neighborhood was charming. The pool was closed but the beach within the community was nearby and quiet. We were a short drive from Cape Charles town center and parking was a breeze. The host was incredibly accommodating; her restaurant recommendations were spot on. I wish we could’ve stayed longer!

Seas The Day of Virginia Beach
Had a great time & Kevin was a great host. The airbnb was very clean and not sandy especially for being so close to the beach. Was in a perfect location, walking distance to the grocery store, boardwalk, & tons of restaurants. Just don't forget to bring linens or towels! I definitely look forward to visiting again.
Quick stats about condo rentals in Chesapeake
Total rentals
40 properties
Nightly prices starting at
G$10,491 GYD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Bethel Beach
- Buckroe Beach
- First Landing State Park
- Kingsmill Resort
- Water Country USA
- Buckroe Beach and Park
- Grandview Beach
- Currituck Beach Lighthouse
- Virginia Beach National Golf Club
- Jamestown Settlement
- Sarah Constant Beach Park
- Wilkins Beach
- Haven Beach
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Bonito St. Public Beach Access
- Grove Beach
- Golden Horseshoe Golf Club
- Outlook Beach