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Condo holiday rentals in Chesapeake

Find and book unique condos on Airbnb

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Popular amenities for Chesapeake condo rentals

Weekly condo rentals

Superhost
Condo in Bayview
4.77 out of 5 average rating, 22 reviews

Bay Breeze At Ocean View Beach Home

KatelinRating, 5 stars1 month ago
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!
Guest favourite
Condo in Virginia Beach
4.91 out of 5 average rating, 54 reviews

Beach Luxury Beachfront

JamesRating, 5 stars1 month ago
This place was great! The view is amazing, very clean, and was described to a T. Very nice!
Guest favourite
Condo in Virginia Beach
4.88 out of 5 average rating, 42 reviews

Shadowlawn Villas II, Suite II

JeniseRating, 5 stars3 months ago
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!
Top Guest favourite
Condo in Sandbridge
5 out of 5 average rating, 53 reviews

Sandbridge Beach - DeepSeaSide Retreat

Tamie Rating, 5 stars1 week ago
The perfect hosts!! Best stocked house we have ever stayed in. Already planning our trip next year!!
Superhost
Condo in Virginia Beach
5 out of 5 average rating, 4 reviews

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!

AldoRating, 5 stars11 months ago
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.
Top Guest favourite
Condo in Cape Charles
5 out of 5 average rating, 10 reviews

The Port - Large condo on Mason Avenue!

DawnRating, 5 stars2 weeks ago
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!
Guest favourite
Condo in Virginia Beach
4.87 out of 5 average rating, 86 reviews

Good Vibes at the Beach

BevRating, 5 stars1 week ago
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
Guest favourite
Condo in Williamsburg
5 out of 5 average rating, 10 reviews

1-Bedroom Condo in Williamsburg, VA

AquilaRating, 5 stars3 weeks ago
Excellent location and responsive host. Great amenities for children and adults. I would definitely stay again!

Pet-friendly condo rentals

Superhost
Condo in Hampton
4.85 out of 5 average rating, 99 reviews

Cozy & Fun Hampton Condo ~ WIFI & W/D!

PatriciaRating, 5 stars2 weeks ago
He had a great time
Top Guest favourite
Condo in Willoughby Spit
4.99 out of 5 average rating, 91 reviews

Beachfront Getaway, Pet Friendly, Mermaid Suite

SaraRating, 5 stars4 weeks ago
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.
Guest favourite
Condo in Ocean View
5 out of 5 average rating, 22 reviews

Ocean Bliss: Cozy Apt Retreat(D)

HabeebulaiRating, 5 stars3 months ago
The house is in an amazing location with lots to do and the host is very communicative and helpful.
Top Guest favourite
Condo in Corolla
5 out of 5 average rating, 27 reviews

Enjoy Sea Life! Steps to the Beach!

MichaelRating, 5 stars2 weeks ago
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.
Top Guest favourite
Condo in Corolla
5 out of 5 average rating, 19 reviews

Oyster & Pearl Beautiful New Single Level Condo

BrendaRating, 5 stars8 months ago
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
Guest favourite
Condo in Corolla
4.97 out of 5 average rating, 36 reviews

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

MartinRating, 5 stars4 days ago
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!
Top Guest favourite
Condo in Corolla
4.97 out of 5 average rating, 77 reviews

Walk to Corolla Village and the Beach!

RebeccaRating, 5 stars2 weeks ago
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!
Guest favourite
Condo in Corolla
4.93 out of 5 average rating, 56 reviews

CrabaCabana in the Center of Corolla

SoniaRating, 5 stars4 weeks ago
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

Top Guest favourite
Condo in Corolla
4.96 out of 5 average rating, 27 reviews

New Beachside Villa: Steps to Sand, Dog-Friendly!

CourtneyRating, 5 stars1 week ago
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.
Guest favourite
Condo in Williamsburg
5 out of 5 average rating, 12 reviews

Wyndham Governor's Green (3 BD Deluxe)

KaraRating, 5 stars3 weeks ago
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.
Guest favourite
Condo in Williamsburg
4.96 out of 5 average rating, 46 reviews

Marriott's Manor Club Ford's Colony 2BD Villa Slee

DorrenRating, 5 stars3 weeks ago
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.
Superhost
Condo in Virginia Beach
4.78 out of 5 average rating, 18 reviews

Beach Quarters Resort- Oceanfront 1 bdrm sleeps 6

CurtisRating, 5 stars5 days ago
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!
Superhost
Condo in Virginia Beach
4.85 out of 5 average rating, 40 reviews

Dolphin Beach condo-amazing view and indoor pool

PamRating, 5 stars8 months ago
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!
Superhost
Condo in Corolla
4.88 out of 5 average rating, 17 reviews

Sea La Vie at The Beach Club - Walk to Beach

MadisonRating, 5 stars1 month ago
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
Top Guest favourite
Condo in Corolla
5 out of 5 average rating, 16 reviews

Wonderful & tranquil beach retreat: 2BR/2BA Condo.

HannahRating, 5 stars2 weeks ago
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!!!
Top Guest favourite
Condo in Cape Charles
4.96 out of 5 average rating, 27 reviews

Bay Creek Blessed at The Fairways

KathrynRating, 5 stars1 month ago
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

Destinations to explore

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  4. Chesapeake
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