Apartment holiday rentals in Chesapeake

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Popular amenities for Chesapeake apartment rentals

Weekly apartment rentals

Guest favourite
Apartment in Virginia Beach
4.91 out of 5 average rating, 54 reviews

Beach Luxury Beachfront

JamesRating, 5 stars1 month ago
This place was great! The view is amazing, very clean, and was described to a T. Very nice!
Top guest favourite
Apartment in Sandbridge
5 out of 5 average rating, 54 reviews

Sandbridge Beach - DeepSeaSide Retreat

MollyRating, 5 stars3 days ago
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.
Superhost
Apartment in Virginia Beach
4.71 out of 5 average rating, 42 reviews

1 Block to Oceanfront & Boardwalk

KendraRating, 5 stars1 week ago
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 .
Top guest favourite
Apartment in Cape Charles
5 out of 5 average rating, 10 reviews

The Port - Large condo on Mason Avenue!

DawnRating, 5 stars3 weeks ago
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!
Superhost
Apartment in Virginia Beach
4.75 out of 5 average rating, 53 reviews

21st Street Condo - 1 block from the Dome

JeffRating, 5 stars4 weeks ago
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.
Guest favourite
Apartment in Virginia Beach
4.87 out of 5 average rating, 86 reviews

Good Vibes at the Beach

BevRating, 5 stars2 weeks ago
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
Guest favourite
Apartment in Williamsburg
4.96 out of 5 average rating, 81 reviews

2 Bedroom Stylish Kingsmill condo

JeanneRating, 5 stars1 week ago
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.
Top guest favourite
Apartment in Virginia Beach
5 out of 5 average rating, 21 reviews

Paradise Cove

KathrynRating, 5 stars2 weeks ago
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

Apartment in Williamsburg
4.67 out of 5 average rating, 21 reviews

Relaxing Retreat Along the Bank of the James River

SherryRating, 5 stars10 months ago
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.
Superhost
Apartment in Hampton
4.85 out of 5 average rating, 99 reviews

Cozy & Fun Hampton Condo ~ WIFI & W/D!

PatriciaRating, 5 stars2 weeks ago
He had a great time
Top guest favourite
Apartment in Willoughby Spit
4.99 out of 5 average rating, 91 reviews

Beachfront Getaway, Pet Friendly, Mermaid Suite

SaraRating, 5 stars1 month ago
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.
Superhost
Apartment in Willoughby Spit
4.79 out of 5 average rating, 33 reviews

August Suite | Beach | Balcony | Fire Pit

MichaelRating, 5 stars1 week ago
loved our stay. cozy home with everything you need and FANTASTIC host who meets all yours demands without hesitation.
Guest favourite
Apartment in Ocean View
5 out of 5 average rating, 22 reviews

Ocean Bliss: Cozy Apt Retreat(D)

HabeebulaiRating, 5 stars4 months ago
The house is in an amazing location with lots to do and the host is very communicative and helpful.
Apartment in Virginia Beach
4.59 out of 5 average rating, 51 reviews

Cozy Modern Spacious Condo with Balcony

MatthewRating, 5 stars27 months ago
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.
Guest favourite
Apartment in Chic's Beach
4.97 out of 5 average rating, 228 reviews

Chic's Beach Rental and Fishing

SaraRating, 5 stars1 week ago
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!
Apartment in Norfolk
4.43 out of 5 average rating, 37 reviews

Modernize Condo at Colonial Place

GarlandRating, 5 stars7 months ago
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

Superhost
Apartment in Williamsburg
4.91 out of 5 average rating, 23 reviews

The Historic Powhatan 2 bdrm

BillRating, 5 stars19 months ago
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
Superhost
Apartment in Virginia Beach
4.85 out of 5 average rating, 41 reviews

Dolphin Beach condo-amazing view and indoor pool

O'KeylaRating, 5 starstoday
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!!
Apartment in Sandbridge
4.81 out of 5 average rating, 27 reviews

Sunny 2BR 1st-Floor | Balcony | Pool

LeahRating, 5 stars1 month ago
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!!
Superhost
Apartment in Virginia Beach
4.57 out of 5 average rating, 51 reviews

Lovely 2 bedroom condo walking distance to Beach

AnnaMaeRating, 5 stars1 month ago
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.
Top guest favourite
Apartment in Cape Charles
4.96 out of 5 average rating, 27 reviews

Bay Creek Blessed at The Fairways

KathrynRating, 5 stars1 month ago
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!
Superhost
Apartment in Virginia Beach
4.82 out of 5 average rating, 57 reviews

Seas The Day of Virginia Beach

ElizabethRating, 5 stars1 month ago
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.
Top guest favourite
Apartment in Williamsburg
5 out of 5 average rating, 7 reviews

Big family 4BR (12) townhouse.

MichelleRating, 5 stars1 week ago
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!
Top guest favourite
Apartment in Virginia Beach
5 out of 5 average rating, 24 reviews

Private Virginia Beach Escape w/ Pool & Fire Pit!

FranklinRating, 5 stars1 week ago
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

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