
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

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!

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.

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

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

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!

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!
Pet-friendly apartment 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.

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.

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.

*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! ♥️
Apartment rentals with a pool

Beautiful Beachfront Condo
The only issue we had was our code for the building and parking did not work at first! Pam was very quick to resolve! There are no elevators in parking garage, I would take my stuff in at the entrance and then park! Dolphin run staff was not much help! We had a second car that we were supposed to get a parking permit for. They just told us to park and not worry about signs that clearly stated towed with no permit. Our car did NOT get towed!

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.

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.

Oceanfront, beach, boardwalk, fun, dolphin, sunris
We enjoyed staying at Kelly's place in VB. Its an ideal location for anyone who wants to stay right at the boardwalk. We witnessed amazing sunrises and moonrises. The ocean was right in front of us and from the 6th floor, the view was expansive. A lot of restaurants were also nearby. Kelly was always very communicative, polite and professional. The apartment was clean with the kitchen well stocked with utensils The bedrooms were of a pretty large size. And parking was on the premises. Overall, it was a wonderful experience and holiday for us. We strongly recommend Kelly's place.

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.
Fantastic location and clean, well-equipped place! Would come back.

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!
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
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- Busch Gardens Williamsburg
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