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Condo vacation rentals in Chesapeake

Find and book unique condos on Airbnb

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Popular amenities for Chesapeake condo rentals

Weekly condo rentals

Top guest favorite
A turquoise mug is positioned on sandy ground, partially surrounded by beach grass. The mug features a logo with an octopus design. The warm sunlight highlights the textures of the sand and grass, creating a calm beach setting.
Condo in Sandbridge
5 out of 5 average rating, 54 reviews

Sandbridge Beach - DeepSeaSide Retreat

MollyRating, 5 stars1 day ago
My family had a wonderful stay at Anne and Bill's place. Their home was perfect for a beach getaway in Sandbridge. It was very comfortable, clean, and had all of the necessities to make for an easy, relaxing trip. Bill met us to let us in and show us around the property and was very friendly. It felt more like staying at a friend's home than a rental. We would love to stay there again any time we make it back to Sandbridge.
Top guest favorite
A modern kitchen features crisp white cabinetry, a stainless steel refrigerator, and a large farmhouse sink. Bright light floods the space through a nearby window, illuminating the granite countertops and the mixer on the counter. Decorative accents include a plant and wine bottle, adding warmth to the area.
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 favorite
A modern kitchen area features warm wooden cabinets and stainless steel appliances. The dining space has white chairs surrounding a round table set with blue plates. Light fixtures illuminate the counter, while a cozy seating area with a side table and lamp is visible in the corner.
Condo in Virginia Beach
4.87 out of 5 average rating, 86 reviews

Good Vibes at the Beach

BevRating, 5 stars2 weeks 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
Superhost
The kitchen features dark cabinetry complemented by white tile backsplash. Stainless steel appliances, including an oven and microwave, are present. A small dish drying area is visible beside the sink, with natural light entering from a nearby window.
Condo in Virginia Beach
4.75 out of 5 average rating, 53 reviews

21st Street Condo - 1 block from the Dome

JeffRating, 5 stars3 weeks ago
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.
Guest favorite
A stone fire pit is illuminated by a lively flame, surrounded by a circular brick wall. Lush greenery and trees can be seen in the background, enhancing the outdoor setting during the evening.
Condo in Williamsburg
4.96 out of 5 average rating, 46 reviews

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

DorrenRating, 5 stars4 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
A view of the Virginia Beach boardwalk stretches alongside the sandy shore, with people strolling beneath a clear sky. Beachfront attractions and palm trees are visible in the distance, while the ocean waves gently lap at the shore, creating a serene atmosphere.
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!
Guest favorite
Condo in Chic's Beach
4.97 out of 5 average rating, 228 reviews

Chic's Beach Rental and Fishing

SaraRating, 5 stars1 week ago
We had an outstanding stay! Three generations and a one night trip and yet this host and house made it feel like a whole weekend getaway. The unit is spacious and wrapped in ocean views! The three rooms are great sizes and the beds were very comfortable so was the temperature in the unit. The kitchen was just like home maybe nicer and fully stocked so you can cook or bake! Ice maker and coolers and so much toys for the kiddos we didn’t have anything with us and yet needed nothing! This was a breathtaking trip in a home away from home and Mike and his cute pups were wonderful company when we crossed paths. We can’t wait to come back and highly recommend this to anyone wanting a care free amazing trip! Don’t think twice, book!
Guest favorite
A busy intersection is captured with a clear blue sky above. Pedestrians are seen waiting at a traffic light, with various buildings visible in the background, including a hotel and a parking garage, indicating a vibrant urban area. Traffic signals are prominently displayed.
Condo in Virginia Beach
4.96 out of 5 average rating, 83 reviews

Beach Chic Remodeled Condo 1 Block from Beachfront

KelseyRating, 5 stars2 weeks ago
We stayed here for 5 nights and really enjoyed it. Restaurants and the beach are an easy walk. I felt very safe. Night time can get a little loud being on a busy intersection, but would not deter me from staying again! Susan was responsive and a great host.

Pet-friendly condo rentals

Superhost
A guest room features two spacious beds adorned with patterned linens. An artistic display of vintage vinyl records decorates the wall above, enhancing the room's character. Warm wooden flooring complements the overall design, while a small nightstand stands between the beds.
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 favorite
A workspace with a wooden desk and a comfortable chair is situated by large windows, offering expansive views of the ocean. Natural light streams in, highlighting the tranquility of the beach outside. The windows are framed by light-colored blinds, with a small plant placed on the desk.
Condo in Willoughby Spit
4.99 out of 5 average rating, 91 reviews

Beachfront Getaway, Pet Friendly, Mermaid Suite

SaraRating, 5 stars1 month 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.
Superhost
A comfortable living area features a large sectional sofa adorned with colorful cushions. Natural light filters through two windows, framed with light curtains. A wooden coffee table sits on a patterned rug, with a flat-screen TV nearby and a side table adding functional charm.
Condo in Willoughby Spit
4.79 out of 5 average rating, 33 reviews

August Suite | Beach | Balcony | Fire Pit

MichaelRating, 5 stars1 week ago
loved our stay. cozy home with everything you need and FANTASTIC host who meets all yours demands without hesitation.
Guest favorite
A fenced backyard features a picnic table, two lounge chairs, and a firepit. String lights hang overhead, providing soft illumination. Lush greenery surrounds the space, enhancing the outdoor setting, while nearby structures indicate the proximity to the rental property.
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 favorite
The open living area features a comfortable sofa accompanied by a patterned armchair, creating a relaxed atmosphere. A coffee table sits in front, adorned with a small decorative arrangement. Modern cabinetry and stainless steel appliances are visible in the adjoining kitchen, complemented by a spacious dining area.
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.
Guest favorite
A shuffleboard table is positioned in the room, complemented by a nautical-themed painting of sailboats on water above. Decorative ship wheel accents the wall, contributing to the beach-inspired decor of the space.
Condo in Corolla
4.97 out of 5 average rating, 36 reviews

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

MartinRating, 5 stars5 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 favorite
A spacious living area is highlighted by vaulted ceilings and large windows that allow natural light to fill the space. A comfortable sectional sofa and a wooden coffee table are present, along with a long kitchen island featuring bar stools. A doorway leads to an outdoor area.
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 favorite
An open-concept living area features a spacious kitchen with quartz countertops, stainless steel appliances, and a large island with bar seating. A cozy red sofa is arranged with decorative pillows, and a striped rug adds texture to the hardwood floor. Natural light streams through the windows.
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 favorite
The exterior of the duplex showcases a welcoming entrance with a sign reading 'Salty Vibes.' Lush landscaping features colorful flower beds and well-maintained grass. The home is framed by a modern fence, providing a clear view of the architectural design and neighboring units.
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.
Top guest favorite
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 favorite
A serene resort view is presented, featuring three white multi-story buildings by a calm pond. The clear water reflects the structures and a fountain creates gentle ripples, enhancing the tranquil atmosphere of the surrounding greenery.
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!
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 favorite
The image captures a serene beach scene, featuring gentle waves lapping at the shoreline. The water reflects sunlight, creating a shimmering effect on the surface. A clear blue sky is visible above, contributing to the tranquil coastal atmosphere.
Condo in Corolla
5 out of 5 average rating, 17 reviews

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

StefanRating, 5 stars2 weeks ago
Fantastic location and clean, well-equipped place! Would come back.
A studio condo is presented, featuring a spacious bed with a white comforter and accent pillows. A ceiling fan provides airflow, while a wall-mounted TV and a light-colored dresser add functionality. Artwork depicting coastal scenes is displayed on the walls, enhancing the inviting environment.
Condo in Virginia Beach
4.79 out of 5 average rating, 24 reviews

Sunny Days Beach Studio on the Boardwalk w/Pool

BrittanyRating, 5 stars1 month ago
Wonderful stay at this lovely condo! The location is phenomenal - Right next to the boardwalk leading to the beach. So many great restaurants within walking distance & easy to access parking & the property itself. Highly recommend!
Guest favorite
An outdoor pool area is presented with a large circular swimming pool, surrounded by loungers and shaded by pergolas. The clubhouse, featuring a welcoming design, is visible in the background against a clear blue sky dotted with clouds.
Condo in Williamsburg
5 out of 5 average rating, 21 reviews

Wyndham Governor's Green, 3 BR Deluxe

SherryRating, 5 stars1 month ago
A very lovely resort. The only disappointment was the WiFi situation. It is very poor WiFi. Most of the time it didn’t work. When we called the front desk, they told us to contact the WiFi provider. When we called, we got a recording that there would be a long wait due to volume of calls, so the WiFi was not fixed during our stay.
Top guest favorite
The exterior of a two-story house is shown, featuring a gray shingle facade and a welcoming front porch. Neatly trimmed shrubs and manicured lawns frame the driveway, while flowering plants add subtle color. A double garage with white doors is visible on the left.
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

    R898 ZAR 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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