
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

Relax in Style: 2BR Condo w/ Balcony at Wyndham GG
We were very pleased with our stay. Check-In was very easy with plenty of text notifications. Check out was easy as well. We were greeted by Club Wyndham timeshare staff and invited to attend a presentation, but the offer was very friendly and not pushy at all. It was a very good experience, and we would love to stay again. We visit our Aunt who lives in Ford's Colony and found this location we'll suited for all of Williamsburg.

Cozy 1 Bd condo, 1 block from the beach!
Charles was very kind and a great host , always answered our messages quickly. The airbnb was very clean and very nice, We loved our stay here !

Wyndham Kingsgate (3 BD LO)
Our family of 6 has a great time. Plenty of space at the unit and the amenities were even more than described. We'll be coming back!

Beautiful & Modern Condo with Prime Location
We had a wonderful stay at Mina’s condo! She was an amazing host—always quick to respond and very accommodating. The home was spotless, spacious, and well-equipped with everything we needed for a comfortable stay. The layout was perfect, and we especially appreciated the clean, modern bathrooms and cozy living space. We’d absolutely stay here again and highly recommend it to anyone looking for a relaxing and hassle-free getaway. Thanks, Mina!

Relax on Island Time, 2 Bed Single Level Condo
We had a wonderful stay and owners were wonderful to work with!! We actually requested an extra day which owner honored. Highly recommend!

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

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!!

Bay Creek Blessed at The Fairways
We loved our weekend stay in Cape Charles and this rental was absolutely perfect for our family. Very well equipped home with lovely decor. Angela communicated every detail that we needed for a seamless check in. Would definitely recommend!
Pet-friendly apartment rentals

New Beachside Villa: Steps to Sand, Dog-Friendly!
Great location near Corolla beach, the place was dog friendly, and the hosts were great! Our first time to OBX & it was very memorable. Would definitely stay again! Hosts were fast to respond & made everything as easy as possible with check in/out. Thank you for a great stay!

Beachfront Getaway, Pet Friendly, Mermaid Suite
We had a great stay. The host was very kind and the space was great.

Cozy & Fun Hampton Condo ~ WIFI & W/D!
Great location for what we needed, close to all options of food and grocery. Only 6 minutes from Boo Williams facility which was perfect. Quiet neighborhood with really nice neighbors. Ideal set up to have our dog with us as well. Loved BuckRoe Beach which was only 10 minutes away. We will be back!

August Suite | Beach | Balcony | Fire Pit
Great place to stay and enjoy the Virginia Beach area! The suite was spotless and very well decorated. Nice outdoor space, and even a balcony to enjoy the sunshine. Loved the quick walk to the beach (She even had some great books available that we took advantage of)!The host was very gracious and kind and our stay was seamless . Just a helpful suggestion: it needed a few more basic items like additional hand towels/kitchen towel ( one was not enough for us three girls), and another accessible mirror for getting ready would be super helpful! Besides that, we all agreed that we would come back for sure! Thank you for a great stay!

Ocean Breeze: New Condo Steps to the Beach
Wonderful location. Perfect size place for our family (2 adults, 1 child, and one dog). Walkable to the beach (a block away) historic Corolla, the park, restaurants. Lynn was fantastic. Responsive, provided great recommendations and her place was clean, cozy, quiet, and had all the amenities we needed. Would happily stay here again.

Walk to beach large 2/2 in "Kingsmill on James"
Gayle’s place was a great location to stay at with our dog!!! Great neighborhood to walk him in and the marina/beach is an added bonus! Gayle was very communicative and check in was easy. The space of the condo was great for a family and large dog! We will definitely be staying again!

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.

Oyster & Pearl Beautiful New Single Level Condo
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
Apartment rentals with a pool

Ocean front best beach, boardwalk, dolphins!
Amazing place. Recommended.

Williamsburg Plantation ThanksGiving Large Condo 2
Amazing experience! communication was amazing! I'm a firm believer that communication sets the tone for an experience. The resort is beautiful! the amenities were top tier. The biweekly poolside party was a hit with the family. We felt safe and very welcomed. Great experience!

Oceanfront Condo with Spectacular Beach View
Jason's place was so beautiful. It feels like home. Warm and comfy. It was clean. I didn't want to leave we were looking for a place to stay. Where we can had a peaceful, relaxed and private time, so we found that and even more at Jason's place. I love it and if winter time was beautiful there, I can't wait for summer. Note: We saw dolphins jumping in the beach from de window of the house. I love it, it was so beautiful.😍

2 Bdrm Condo at The Historic Powhatan Resort
Very nice. I highly recommend this place. Very nice inside and I love the Powhatan Resort also.

2BD2BA Condo w/Pool2Blocks2Beach
Came with my girls for a conference at the Beach. Salt and Serenity was super peaceful, felt private and quiet. Beds were super comfy and the water pressure in the showers was awesome. We had everything we needed in the kitchen and all amenities were as described. Susan was a great, responsive host and made accommodations for our early check-in. And all the restaurant suggestions were a hit! Would definitely come again!

Good Vibes at the Beach
A great find. Everything we needed, including a grocery store, was walkable and convenient. Loved being 2 blocks from the ocean and boardwalk. Excellent space and very comfortable. Colin is an excellent host. Always addressed our questions and needs in a timely fashion. We will be back!

Lovely 2 Bedroom Condo With Pool And Amenities
Loved the condo! Great space while we waited for our new home to be ready. Enjoyed all the amenities and options on site. Nicholas was also great to ensure we got in and were satisfied with everything!

Renovated 2 Bedroom Beach Condo with Balcony
This boost was very responsive and understanding due to a mistake I made. The home was beautiful and if you’re a person that loves a nice walk to your destination, this condo is close to everything. 20 minute walk from literally everything! I will stay again on our next visit.
Quick stats about apartment rentals in Chesapeake
Total rentals
40 properties
Nightly prices starting at
£38 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
- Kingsmill Resort
- First Landing State Park
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- Virginia Beach National Golf Club
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- Chrysler Museum of Art
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