Photo by Sarah Chiricosta

Search Condo Rentals in Chesapeake

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chesapeake condo rentals

8.0 out of 10, Very Good, (4)
"Perfect for what we needed for one day layover before outer Banks"
Canada
Michael L.
The price is AED 459
AED 613 total
includes taxes & fees
29 Dec - 30 Dec
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
10.0 out of 10, Exceptional, (1)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is AED 479
AED 635 total
includes taxes & fees
27 Jan - 28 January 2026
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
The price is AED 424
AED 572 total
includes taxes & fees
29 Dec - 30 Dec
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
10.0 out of 10, Exceptional, (39)
"Exactly how described, nice location, host is very responsive."
United States
Melissa B.
The price is AED 492
AED 1,498 total
includes taxes & fees
5 Jan - 6 January 2026
Awesome Beach Getaway! 1 block to the ocean, with a big pool in the back.
8.0 out of 10, Very Good, (1)
"This room is not oceanfront, there is no view of the ocean.In my experience oceanfront means full on view of the ocean, ocean view means side view. Obstructed view is just that. What we had was NO view of ocean. Even though it says that. Very nice condo otherwise.Finding your parking space is like looking for Waldo,kinda crazy.One suggestion is a towel or bath mat to step on when you get out of the shower. There are no extra towels for that."
United States
lori h.
The price is AED 839
AED 2,425 total
includes taxes & fees
30 Dec - 31 Dec
New! 3Bd 2Bth Oceanfront / Pool / Boat /224b
2.0 star property
9.0 out of 10, Wonderful, (6)
"Great place to stay! Super close to the beach and it wasn’t too crowded. Has basics for what you need. The second parking spot was a little further away than ideal but we made it work. "
United States
Danni R.
The price is AED 803
AED 2,279 total
includes taxes & fees
28 Dec - 29 Dec
NEW! Oceanfront Triton's Treasure 3 Bd / Pool/ Gym
10.0 out of 10, Exceptional, (4)
"Great location , with restaurant across the street Amy family and I enjoyed our stay "
United States
shantielle T.
Cozy 3-bedroom condo with AC and WiFi in charming Virginia Beach
9.2 out of 10, Wonderful, (35)
"Excellent host! "
United States
Cindy S.
The price is AED 1,087
AED 2,590 total
includes taxes & fees
28 Dec - 29 Dec
❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views

Condo in Northeast Virginia Beach

Oceanfront Condo with Indoor Pool
8.0 out of 10, Very Good, (3)
"Our daughter and family enjoyed the pool and beach. Thanks for prompt responses when I had questions!"
United States
Jan F.
Oceanfront Condo with Indoor Pool
8.8 out of 10, Excellent, (5)
"We attended a wedding and this place was the perfect location just across the street from the venue. There was another car parked in our reserved spot that made it difficult to get the key fob and return it but other than that it was a great place to stay. "
United States
Tracy N.
The price is AED 846
AED 2,331 total
includes taxes & fees
30 Dec - 31 Dec
New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym
10.0 out of 10, Exceptional, (2)
"Great stay, wonderful location, and the place is bigger than it looks in the pictures. Would definitely stay again"
United States
John C.
The price is AED 899
AED 2,396 total
includes taxes & fees
4 Jan - 5 January 2026
New! Beachfront 3bd / 2Bth/Pool/Hot tub 104A

Condo in Northeast Virginia Beach

High floor, Ocean View Condo
The price is AED 511
AED 920 total
includes taxes & fees
28 Dec - 29 Dec
High floor, Ocean View Condo
9.4 out of 10, Exceptional, (23)
"Proximity to the ocean was great."
United States
Raymond J.
The price is AED 1,398
AED 3,541 total
includes taxes & fees
29 Dec - 30 Dec
Beachfront Penthouse! 4Bd/3Bth
6.6 out of 10, (4)
"Everything was clean and beautiful "
United States
Antwaine J.
The price is AED 643
AED 1,410 total
includes taxes & fees
28 Dec - 29 Dec
Mountain Jade Garden Condo Resort 2 bed 2 bath near Newport News City Center
8.8 out of 10, Excellent, (18)
"Good visit"
United States
Elizabeth E.
Virginia Beach, oceanfront, boardwalk, beach, fun, dolphins
9.4 out of 10, Exceptional, (20)
"Great stay and great condo!"
United States
Kevin F.
Waterfront Penthouse! 4bd/4Bth, 3000 sqft, 2 Decks
8.0 out of 10, Very Good, (15)
"Loved the location and the avtivitoes/events in the neighborhood."
United States
Smain K.
The price is AED 1,833
AED 2,799 total
includes taxes & fees
28 Dec - 29 Dec
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesapeake Hotel Reviews

Frequently asked questions

Why book your condo in Chesapeake with Expedia?
Booking a condo in Chesapeake is as simple as clicking on your travel dates and choosing an option that suits your style. Looking for something upscale or budget friendly, or a stay that also features a pool and free WiFi? Use Expedia's search filters to further narrow your search results and find the perfect fit.
How can I find cheap condos in Chesapeake?
An excellent way to find cheap condos in Chesapeake is with Expedia's easy-to-use filter tool. Tailor your search results by star rating, budget and amenities to discover unbeatable deals in a few clicks.