Apartment holiday rentals in Chesapeake

Find and book unique apartments on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Chesapeake apartment rentals

Weekly apartment rentals

Superhost
Apartment in Williamsburg
5 out of 5 average rating, 3 reviews

Relax in Style: 2BR Condo w/ Balcony at Wyndham GG

JamesRating, 5 stars1 month ago
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.
Guest favourite
Apartment in Virginia Beach
4.86 out of 5 average rating, 85 reviews

Cozy 1 Bd condo, 1 block from the beach!

BladimirRating, 5 stars4 months ago
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 !
Guest favourite
Apartment in Williamsburg
4.9 out of 5 average rating, 10 reviews

Wyndham Kingsgate (3 BD LO)

JohnRating, 5 stars2 weeks ago
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!
Apartment in East Ocean View
4.85 out of 5 average rating, 71 reviews

Beautiful & Modern Condo with Prime Location

InettaRating, 5 stars1 month ago
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!
Apartment in Corolla
4.92 out of 5 average rating, 12 reviews

Relax on Island Time, 2 Bed Single Level Condo

ZereeRating, 5 stars6 months ago
We had a wonderful stay and owners were wonderful to work with!! We actually requested an extra day which owner honored. Highly recommend!
Superhost
Apartment in Corolla
4.88 out of 5 average rating, 17 reviews

Sea La Vie at The Beach Club - Walk to Beach

MadisonRating, 5 stars1 week ago
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
Apartment in Sandbridge
4.88 out of 5 average rating, 24 reviews

Sunny 2BR 1st-Floor | Balcony | Pool

LeahRating, 5 stars1 week 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!!
Top guest favourite
Apartment in Cape Charles
5 out of 5 average rating, 24 reviews

Bay Creek Blessed at The Fairways

PaulaRating, 5 stars7 months ago
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

Top guest favourite
Apartment in Corolla
4.96 out of 5 average rating, 23 reviews

New Beachside Villa: Steps to Sand, Dog-Friendly!

Devon Rating, 5 stars1 week ago
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!
Top guest favourite
Apartment in Norfolk
4.99 out of 5 average rating, 89 reviews

Beachfront Getaway, Pet Friendly, Mermaid Suite

LanceyRating, 5 stars3 weeks ago
We had a great stay. The host was very kind and the space was great.
Superhost
Apartment in Hampton
4.84 out of 5 average rating, 96 reviews

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

KariRating, 5 stars2 days ago
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!
Superhost
Apartment in Norfolk
4.84 out of 5 average rating, 25 reviews

August Suite | Beach | Balcony | Fire Pit

AngieRating, 5 stars2 days ago
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!
Guest favourite
Apartment in Corolla
5 out of 5 average rating, 22 reviews

Ocean Breeze: New Condo Steps to the Beach

PeterRating, 5 stars5 months ago
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.
Top guest favourite
Apartment in Williamsburg
4.97 out of 5 average rating, 108 reviews

Walk to beach large 2/2 in "Kingsmill on James"

SydneyRating, 5 stars6 months ago
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!
Guest favourite
Apartment in Norfolk
5 out of 5 average rating, 22 reviews

Ocean Bliss: Cozy Apt Retreat(D)

HabeebulaiRating, 5 stars2 months ago
The house is in an amazing location with lots to do and the host is very communicative and helpful.
Top guest favourite
Apartment in Corolla
5 out of 5 average rating, 19 reviews

Oyster & Pearl Beautiful New Single Level Condo

BrendaRating, 5 stars6 months ago
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

Guest favourite
Apartment in Virginia Beach
4.9 out of 5 average rating, 52 reviews

Ocean front best beach, boardwalk, dolphins!

LuciaRating, 5 stars3 weeks ago
Amazing place. Recommended.
Superhost
Apartment in Williamsburg
4.8 out of 5 average rating, 5 reviews

Williamsburg Plantation ThanksGiving Large Condo 2

KitRating, 5 stars9 months ago
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!
Guest favourite
Apartment in Virginia Beach
4.9 out of 5 average rating, 67 reviews

Oceanfront Condo with Spectacular Beach View

EsmeRating, 5 stars5 months ago
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.😍
Apartment in Williamsburg
4.8 out of 5 average rating, 10 reviews

2 Bdrm Condo at The Historic Powhatan Resort

LoriRating, 5 stars23 months ago
Very nice. I highly recommend this place. Very nice inside and I love the Powhatan Resort also.
Guest favourite
Apartment in Virginia Beach
4.92 out of 5 average rating, 12 reviews

2BD2BA Condo w/Pool2Blocks2Beach

KrystleRating, 5 stars1 month ago
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!
Guest favourite
Apartment in Virginia Beach
4.87 out of 5 average rating, 85 reviews

Good Vibes at the Beach

MarceeRating, 5 stars7 months ago
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!
Apartment in Williamsburg
4.83 out of 5 average rating, 12 reviews

Lovely 2 Bedroom Condo With Pool And Amenities

BethanyRating, 5 stars9 months ago
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!
Apartment in Virginia Beach
4.73 out of 5 average rating, 60 reviews

Renovated 2 Bedroom Beach Condo with Balcony

StevenRating, 5 stars3 weeks ago
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

  1. Airbnb
  2. United States
  3. Virginia
  4. Chesapeake
  5. Apartment rentals