
Apartment holiday rentals in Chesapeake
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Top-rated apartment rentals in Chesapeake
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Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals

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

Sandbridge Beach - DeepSeaSide Retreat
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.

1 Block to Oceanfront & Boardwalk
This was a wonderful place to stay . Everything was in walkable distance . Very clean and cozy ! The Host was great as well letting us know all the details and instruction's very clearly .

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!

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.

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

2 Bedroom Stylish Kingsmill condo
Lovely stay. Kingsmill setting is beautiful. So much to do in Williamsburg area. Dave’s place was so comfortable, clean, well appointed and convenient to all.

Paradise Cove
We liked the location of this apartment and the lovely extra hospitality touches. There is noise from the above apartment, so make sure to bring your earplugs in case you get heavy footed neighbors. Beds were comfortable, blackout curtains were a nice touch, and the place was nice and clean and pretty.
Pet-friendly apartment rentals

Relaxing Retreat Along the Bank of the James River
Very nice place peaceful. We enjoyed the balcony. The place was close to everything. We really enjoyed our stay wle will definitely be back. The steps where a little to much but great overall.

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.

Cozy Modern Spacious Condo with Balcony
My daughter and I had a great stay. I didn't see the negative that was posted in other reviews. Very cozy and simple place; the only negative is based on my personality. I like to know in advance check-out procedures to execute how the sponsor wishes—plenty of close-by activities and close enough to the beach. I wouldn't hesitate to stay here again.

Chic's Beach Rental and Fishing
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!

Modernize Condo at Colonial Place
Christopher’s place was great. He was very accommodating and responsive. My family and I had a great time here. I would 100% book again.
Apartment rentals with a pool

The Historic Powhatan 2 bdrm
Colleen was an excellent host! She was very accommodating and understanding when she walked me through the process on how to book the condo. I would definitely recommend her in this place. It is centrally located in the Williamsburg area very close to all the sites and tours around the area. The check in process was very smooth and the staff were very friendly. 10 out of 10 recommend

Dolphin Beach condo-amazing view and indoor pool
Nikola’s place was actually great, better than expected honestly. I recommend he upload updated quality pictures. No longer have carpet, rooms are very spacious. Every time I travel I be so nervous about the space and cleaning and even tho I clean again the place was very clean. I wasn’t expecting that. Only little issue is when it came to the hot water….the hot water didn’t last long for the showers for everyone to shower and, couldn’t get the water hot coming out the sinks. Nikola place is located in a more quieter end of the beach and not the main center strip area of the beach. Great oceanfront view. Nikola was a great communicator and responded sooner than 10mints. Gave straight forward step by step directions. Especially compared to other places reviews for this exact same building. We had no major issues(other than the water) we enjoyed our trip and stay. We would book again. Thank you Nikola!!

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!!

Lovely 2 bedroom condo walking distance to Beach
Outstanding spring vacation spot. My favorite time to visit the beach, just before it gets busy. Sammie’s space is everything you’ll need for your next beach sojourn.

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.

Big family 4BR (12) townhouse.
Lovely, lovely place! Very comfortable. Super clean. Carefully stocked. Wonderful community ammenities. Ideal location for Williamsburg, Jamestown, and Busch Gardens. Will choose to stay there again if we return to the area. Thank you!

Private Virginia Beach Escape w/ Pool & Fire Pit!
Very nice owners! Very west coast feel !! I will be back.
Quick stats about apartment rentals in Chesapeake
Total rentals
40 properties
Nightly prices starting at
$64 SGD 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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- 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
- Chrysler Museum of Art