
Condo holiday rentals in Chesapeake
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Top-rated condo rentals in Chesapeake
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Popular amenities for Chesapeake condo rentals
Weekly condo rentals

Bay Breeze At Ocean View Beach Home
Gorgeous ocean views, great location, the balcony was the favorite spot the entire stay! Comfortable furniture, nice little cozy condo! Highly recommend the stay if you’re in the area!

Beach Luxury Beachfront
This place was great! The view is amazing, very clean, and was described to a T. Very nice!

Shadowlawn Villas II, Suite II
We had a fantastic stay at Arica’s condo! The neighborhood was lovely—quiet, safe, and just a short walk to the boardwalk, making it the perfect location for enjoying Virginia Beach. The condo itself was beautifully decorated, with a cozy and inviting atmosphere that made us feel right at home. Everything was thoughtfully arranged, and the space had all the comforts we needed for a relaxing stay. Arica was a great host, ensuring everything was seamless from start to finish. We would absolutely stay here again and highly recommend it to anyone looking for a great place near the beach!

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

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!
We stayed a week at Kerri’s place in Virginia. She went above and beyond our expectations, very communicative and organized. She offered a ton of information and insights before and during our stay. Her place offers a delightful and relaxing getaway experience. The resort's picturesque location by the ocean provides stunning views and a serene atmosphere. The rooms are spacious, well-appointed, and comfortable, ensuring a pleasant stay. The resort amenities such as the pool, spa, and on-site restaurants add to the overall wonderful experience. The staff is friendly, accommodating, and dedicated to providing top-notch service to guests. Whether you're looking to relax by the beach or explore the nearby attractions, Boardwalk Resort is a fantastic choice for a vacation in Virginia. I would definitely recommend and revisit Kerri’s place.

The Port - Large condo on Mason Avenue!
This is truly a hidden gem in Cape Charles! We recently stayed for the long holiday weekend and loved every minute of our trip. The apartment is absolutely beautiful and the location couldn't be better. We enjoyed having the ability to walk around town and have stores and restaurants so close by. The host was friendly and helpful and quick to respond to any questions we had. We look forward to staying here again!

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

1-Bedroom Condo in Williamsburg, VA
Excellent location and responsive host. Great amenities for children and adults. I would definitely stay again!
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.

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.

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

*New*OceansideCondo PetsOK Pool GameRoom No Stairs
Perfect accommodations for family of 3 and 2 small dogs. Friendly walking area for dogs. The condo was perfectly clean. We loved sitting outside drinking coffee and letting our dogs enjoy the outdoors. We were in a B unit. Pool was perfect and clean after a long day at the beach. We appreciated the wagon to hall our beach gear. We used the public parking which was a 3 minute drive. We are not much for crowds so the location was ideal. I like to cook and the kitchen has everything you need. Local restaurants and fish markets were friendly and helpful. Highly recommend this condo and Lisa was very helpful. We will return!

Walk to Corolla Village and the Beach!
What a lovely gem of a home! Perfect location as it was walkable to beach. Very kind to provide beach chairs, wagon, beach towels and beach umbrella. Spotlessly clean. Only surprise was no shampoo/body wash which was unexpected. Otherwise a perfect experience!

CrabaCabana in the Center of Corolla
Our family had a wonderful stay at the CrabaCabana. It’s about a seven minute walk to the beach and everything was as listed. Kim also provided great suggestions for things to do in the area. She’s an excellent host and took care of anything that needed her attention promptly with perfect communication. We definitely would recommend it to anyone wishing for a home away from home! ♥️
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.

Wyndham Governor's Green (3 BD Deluxe)
this is a great place to stay. Roomy and comfortable. Having three bedrooms and four beds is a real find! The communication about check-in was great. We would love to stay here 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.

Beach Quarters Resort- Oceanfront 1 bdrm sleeps 6
We really enjoyed our stay and will be back. The staff were so helpful and friendly! Location,access to the beach, restaurants and shopping were perfect!

Dolphin Beach condo-amazing view and indoor pool
Squeaky Clean-Extremely Responsive Host-Room looked exactly like the booking images-we were able to check in early-we would stay in this unit again-Thank you Niko!

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

Wonderful & tranquil beach retreat: 2BR/2BA Condo.
This was wonderful! Such a homey space located in an ideal area with every amenity and local attraction nearby. Thank you so much for having me!!!

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!
Quick stats about condo rentals in Chesapeake
Total rentals
40 properties
Nightly prices starting at
$83 NZD 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
- Buckroe Beach
- Bethel Beach
- Water Country USA
- First Landing State Park
- Kingsmill Resort
- Buckroe Beach and Park
- Grandview Beach
- Currituck Beach Lighthouse
- Jamestown Settlement
- Sarah Constant Beach Park
- Haven Beach
- Virginia Beach National Golf Club
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Outlook Beach
- Kiptopeke Beach