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

North End Beach Cottage Apt - One Block from Beach
Ritamarie’s place was super cute!! I had such a wonderful stay. The place was clean and inviting just like the pictures suggested. The walk to the beach was quick, easy, and BEAUTIFUL. This place was perfect for my first solo trip, as the neighborhood felt safe and I really got to feel like a local! The secluded beach was exactly what I was looking for, far away from the touristy attractions. I would definitely suggest this place for anyone looking for a nice quiet getaway. Definitely would stay again.

Sojourn Guest House: Buckroe Beach Suite B
The apartment is cute and very modern. Everything was clean. The neighbors were friendly. The video was a novel idea for check-in.

2 Bdrm Condo 1 block from VB Oceanfront
The rental unit far exceeded our expectations! First and most important was how clean everything is. Shawna really caters to her renters by taking the time to have items on hand in case you forget to bring them. My only issue was that there was only one parking spot for the rental unit. I realize that this is out of Shawna’s control. Otherwise this was a perfect trip with a great place to stay—planning to come back!

Comfy 3 Bedroom Hideaway Minutes From H.U. & Beach
We visited family in the area so finding it wasn’t hard. We had an amazing visit the kids loved the place the neighbors were very friendly. We had a lot of fun and felt right at home Peter was very nice and accommodating with our extended check out which was a big help and also gave us great recommendations on places to visit. We do place to stay again in the future.

LiveEOV: Beachcomber Two
We loved the location. Very short walk to the beach, and short drives to restaurants, grocery stores and shops. The bed I slept in was super comfortable and the living room furniture was also comfortable for reading or watching TV. The kitchen was well equipped. The keypad entry was really convenient and easy to operate. We really enjoyed our weekend stay.

Quaint Quarters Oceana
Quaint Quarters Oceana is a very nice clean, comfortable, quiet Airbnb in a nice neighborhood. There are so many amenities with a lot of thought for guests. It's a great size for 2. Shawn is a great host, communicates well for check in, checking in to make sure guests are comfortable. Great location for beaches, restaurants ,shopping, local attractions.

Modern Luxury Peace & Quiet.
Amazing suite in a private and quiet section of chesapeake, large fenced in yard was amazing for the kids and or dog to run and play. Beautiful interior and very friendly and responsive hosts. 10/10 would reccomend !

Granny-Chic Suite: King Bed & Washer/Dryer
Perfect place for 2 people! Everything we needed was there. We had a little trouble with the TV and they came right away to help! Answered questions immediately. Very nice, clean rental. Close to Historic Yorktown and not far to Williamsburg! Planning to return.
Private apartment rentals

Serene Tree House Retreat | Spacious 1br/1bth Home
Everything was great and just as described in the listing.

The Rosalie Suite 2, Steps from Norfolks Hospitals
It was perfect for my brief stay and will be ideal for a return trip for a longer stay.

Entire Apartment - No Cleaning Fees!
This was my first time booking an airbnb and it won't be the last. Need I say Jamey set the standard pretty high. Jamey was a great host! You get more than what you pay for. The airbnb was clean, well decorated, and ultimately peaceful. Jamey was responsive and made sure everything was cool. The location felt safe and cozy. I would highly recommend this airbnb for a comfortable stay.

English Basement Hide-Away
This basement getaway was absolutely beautiful! We were able to walk all of downtown Portsmouth that included multiple little shops, a few museums (including the children’s museum), a playground just around the corner, the river walk, beautiful water sites of the naval ships and a couple of little local vendors and a small car show. This little town was very welcoming and cute!

Romantic Coastal Retreat w/ Private Balcony
Perfect location- we were able to walk everywhere we wanted to eat and the beach is also just a few blocks away! The space was beautifully decorated and we loved enjoying our coffee and breakfast out on the deck in the mornings.

Sandbridge Beach Bay Getaway
We loved our beach getaway because of our accommodation, it was private and peaceful and had everything we needed! Very clean and furniture done in great taste! We spent a whole week and we didn't want to leave. We especially loved the deck with all the beautiful plants and that we could hear the ocean especially at night! A big plus! We are definitely going back! Jules and Scott, the hosts were so welcoming and kind to us and always helpful. The short walk to the beach was beautiful and so easy! What a gem this place is! We highly recommend! Eric & Vivian

Beach Oasis- Apartment steps from the sand!
The stay was wonderfull, the unit was just like the picture and the beach was right at my finger tips even got to see dolphins right at the beach.

Georgie's Brick Air BNB
My children and I really enjoyed your space. We were surprised with all of the accommodations that was included in our stay, and made it easy for my babies to pair up and bond with each other. We were truly comfortable and it felt as if we were in our own home. Coming to the area so we could welcoming in our new addition to our family was worth it.. Thanks again for renting your unit to me I most definitely will be back in about two too four Weeks if you would have me.
Apartment rentals with a hot tub

*No Resort Fees Powhatan 4 bdrm
The place was better than we even imaged! We had such a wonderful vacation. So much space and in an excellent location. Everyone was very helpful and check in was easy. Thank you!

Sunset Retreat
Great location. Beautiful park next door and beach. We felt safe. Jose Tequila’s has good drinks. Aimee is responsive as a host. The place can get loud at night - we were awakened by people dragging furniture at 3am upstairs and kids yelling in the hallway. The place smelled like smoke that comes in through the pipes under the kitchen sink. Great views and nice kitchen. Well stocked. Aimee left a complimentary bottle of wine.

Bayside condo on the beach in Sandbridge
We had a wonderful getaway for my wife’s first Mother’s Day at Sandbridge with our 3 month old. Eddi was accommodating and flexible with our check-in, providing clear instructions that made it easy. The condo was clean and had a great bay view. The kitchen was well-stocked for a comfortable stay. Eddi has made the condo feel so homey we were perfectly fine hanging out in the condo and enjoying the view. The location was quiet, and Jose Tequila restaurant was nearby. We also tried Margie’s Crabhouse nearby. We’re more than pleased and hope to return!

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.

Cape Henry Full Suite Inn at Old Beach
Very responsive and accommodating! The patio was so peaceful!
Quick stats about flat rentals in Chesapeake
Total rentals
150 properties
Nightly prices starting at
£8 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
Destinations to explore
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Bethel Beach
- Buckroe Beach
- First Landing State Park
- Kingsmill Resort
- Currituck Beach Lighthouse
- Virginia Beach National Golf Club
- Water Country USA
- Grove Beach
- Sarah Constant Beach Park
- Buckroe Beach and Park
- Golden Horseshoe Golf Club
- Norfolk Botanical Garden
- Haven Beach
- Wilkins Beach
- Cape Charles Beachfront
- Kiptopeke Beach
- Grandview Beach
- Jamestown Settlement
- Bonito St. Public Beach Access