
Apartment vacation 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

Home away from home
We had an overall great stay at Sam’s place! My group and I were only in town for one night for a concert and this place accommodated us very well. It was exactly as described and everything was clean. It may seem small but it holds 6 people very comfortably! It was easy to find and easy to check-in. Thank you for hosting us and accommodating and early check-in!

North End Beach Cottage Apt - One Block from Beach
Our stay here was fantastic! Very close to the beach which you can walk to, and only a short drive away from the waterfront that has great restaurants and lots to do! The place itself was clean, quiet and the perfect size for 2 people. If you’re looking for something with great amenities for the size, and in a great location this is it!

2 Bdrm Condo 1 block from VB Oceanfront
This was our first time in Virginia Beach, and this stay was the perfect choice! The space was spotless and exactly as pictured. We really appreciated the thoughtful extras—games, snacks, and awesome beach chairs—that added such a special touch. The location was ideal, just a short walk to the boardwalk, beach, and Atlantic Ave., with plenty of activities nearby. We barely needed our car, though having a designated parking spot was definitely a plus, even if space was a bit tight. The kids were captivated by the military jets flying overhead—it really added to the unique vibe of the area. The free trolley and bus passes were a wonderful bonus, too! This place was a great fit for our family, especially with the easy access to the sports complex and convention center. We hope to return—thank you!

LiveEOV: Beachcomber Two
The place was great it had everything that we needed it was walking distance to the beach

Shipside Suite~Modern~ Fast WI-FI~Cozy
Nice clean place , easy to find and worked well for me and my two children while we were in town.

Sandbridge Beach Bay Getaway
We loved our stay at Jule’s place. She was incredibly helpful with local recommendations and perfect communication. Her spot was well located for our visit to False Cape State Park. Would absolutely stay here again!

Oceanfront Views! 2 BR, 2 BATH!
Our stay was amazing!. Sierra's place was impeccable. The place was spotless, just as advertise in the pictures. I'll be booking again soon.

Spacious Recently Renovated Apartment
Sammy and JB were fantastic hosts. The apartment was WAAAAAY bigger than the photos portrayed and the area was quiet and seemed safe to walk around in. everything was clean. I personally fell in love with the comforters on the bed.
Private apartment rentals

Poseidon - 120 Year Old Beach Cottage with Sauna
We were sad when it was time to come home, we didn’t want to leave! Our home away from home was immaculate. Instructions for parking and entrances were detailed and very easy to figure out. John responded to all texts promptly. Everything we needed was there. The landscaping, the gardens, the seating areas outside were absolutely gorgeous! There was even a mama bird nesting with her baby in the flowers outside. And the backyard is the beach! It was a perfect place for relaxation and enjoying the outdoors. John even provided seven days of perfect weather! ☀️ Thank you for a wonderful stay!

Marina View - One Bedroom Condo
Good location, good amenities, and helpful staff

Sojourn's Sea Views with Balcony Sleeps 4
We had a great stay at Sojourn's place! We were impressed with the neighborhood and location. The beach is right around the corner and there is plenty of areas to walk around the neighborhood. We didn't try any of the restaurants, but there were some within walking distance which is nice. Sojourn's place itself was lovely and clean. Not only were the essential necessities provided, but there were additional amenities and gestures that really made us feel welcomed. Sojourn was very responsive when we had questions and also reached out and anticipated our questions which made the whole visit very easy and seamless. We visit Virginia Beach often and look forward to staying at Sojourn's place again!

The Lounge
I enjoyed the space. It was cute and quaint for my short stay in the area. Ameenah was friendly prior to and after my checkout. The space was a hit for my grandkids too!!! The loft had everything needed for a comfortable stay.

Spiral Loft
Good host, active communication, nice neighbourhood, great place to stay

Works 4 Me: New listing
Wendy was an exceptional host. She was always very timely in her responses if we had any questions/concerns. The property was so beautiful and Wendy made my husband and I feel right at home. We wouldn’t hesitate to book with Wendy again! :)

Beach Luxury Oceanfront
We have visited Virginia Beach numerous times in the last 20 years. This was, by far, the most pleasant visit we ever had. Magued was an exceptional host, responding quickly to any questions. The unit was immaculately clean and well furnished. Sitting on the balcony, listening to the ocean's roar, and watching the dolphins' daily migration was the best part! We would definately stay again.

Newly Built Apt Near Oceanfront
Larry’s place was exactly as advertised and exactly what me and my group needed for our work trip for the weekend! The place is clean and spacious and Larry was very easy to get in contact with if you needed anything. Would absolutely recommend.
Apartment rentals with a hot tub

*No Resort Fees Powhatan 4 bdrm
We had a wonderful stay. The accommodations were outstanding, the staff was also outstanding.

Kingsgate 1 BedrooM
Enjoyed my stay and will definitely stay again!! Beautiful and comfortable interior with so many option for things to do on site. Great area of town.

KingsGATE Resort 1 Bedroom
Had a great time in Williamsburg, VA. Staying at Michael’s place made it an easy place to rest and recharge in between activities. Having multiple pool options was delightful, we swam and soaked almost every night we were there. Sitting on the private back porch in the mornings with my coffee under the crepe Myrtle was idyllic. The entire place was super clean, inside and outside. And most importantly, the beds were high quality and comfortable!

Williamsburg King's Creek Plantation 1BR, 1BA Unit
We used this space while our home was being worked on, do it was more of a “staycation” and did not use all of the amenities. The space was clean and newly renovated, so we were pleased with how nice things were. I highly recommend it for people visiting the Williamsburg area. Great location to Busch Gardens, W&M, etc. The only negative is that it is a time share, and they don’t take no for an answer.

Bayside condo on the beach in Sandbridge
We absolutely loved our stay . The Condo was beautiful and Eddi was kind she allowed me and my sister to check in early. The beach at Sandbridge is lovely we had a nice time .

Sunset Retreat
It's exactly what you are looking for. Quiet, private, and surprisingly spacious. Aimee is a great host she is very up front about everything gives great details on check-in and locating everything. once we walked into the condo it was the little things setup that made the stay very easy to get settled, she is a very thoughtful and you can tell that she cares about her condo and your stay. I highly recommend staying here.

Cape Henry Full Suite Inn at Old Beach
Great spot and amazing location. Super responsive host but still very private location for the set up. The porch sitting paid for itself ! Would definitely not hesitate to stay here again.

Barclay Towers Ocean Front 2, Virginia Beach
It is a beautiful place, close to everything, the only dislike is we saw roaches on our last 2 days of our stay. Than we notice the roach traps.
Quick stats about apartment rentals in Chesapeake
Total rentals
150 properties
Nightly prices starting at
G$2,098 GYD before taxes and fees
Total number of reviews
5.4K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
30 properties have a pool
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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
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Outlook Beach
- Kiptopeke Beach