Search and Rent Chesapeake Condos

    price find illustration
    Change your mind
    Our total price for your stay includes taxes and fees
    deals illustration
    Treat yourself
    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Condo Rentals in Chesapeake

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

10.0 out of 10, Exceptional, (1)
"Very clean , great location. Will stay there again!!!"
$198 nightly
The price is $228
Jul 6 - Jul 7
Total includes taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

$182 nightly
The price is $209
Jul 6 - Jul 7
Total includes taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

$194 nightly
The price is $223
Jul 7 - Jul 8
Total includes taxes and fees
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

2.5 star property
9.0 out of 10, Wonderful, (2)
"Good location and spacious rooms. Good stay!"
$208 nightly
The price is $239
Jul 7 - Jul 8
Total includes taxes and fees
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

NEW Updated! Oceanfront Sanctuary - Sand and Sea

2.0 star property
10.0 out of 10, Exceptional, (4)
"We had a great stay. Unit was spacious, well appointed and decorated. Our family of 4 were very comfortable. Access to the beach a breeze. Nice location away from the touristy boardwalk. "
$695 nightly
The price is $811
Jul 1 - Jul 2
Total includes taxes and fees
NEW Updated! Oceanfront Sanctuary - Sand and Sea

New! 3Bd 2Bth Oceanfront / Pool / Boat /224b

$759 nightly
The price is $886
Jul 13 - Jul 14
Total includes taxes and fees
New! 3Bd 2Bth Oceanfront / Pool / Boat /224b

New! 3Bd 3Bth Oceanfront / Pool / Gym / Beach

$755 nightly
The price is $887
Jun 24 - Jun 25
Total includes taxes and fees
New! 3Bd 3Bth Oceanfront / Pool / Gym / Beach

Waterfront Penthouse! 4bd/4Bth, 3000 sqft, 2 Decks

9.6 out of 10, Exceptional, (17)
" Very nice place. Loved the view of the bay and the ocean from the upper balcony."
$993 nightly
The price is $1,163
Jun 24 - Jun 25
Total includes taxes and fees
Waterfront Penthouse! 4bd/4Bth, 3000 sqft, 2 Decks

New Oceanfront Penhouse 2 Decks! Sunrise / Sunsets

$891 nightly
The price is $1,037
Jun 25 - Jun 26
Total includes taxes and fees
New Oceanfront Penhouse 2 Decks! Sunrise / Sunsets

New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym

8.0 out of 10, Very Good, (1)
"We had a good time! We were concerned about the pool being closed and there being no warning of that, I also messaged Ryan and asked and I never heard anything back."
$704 nightly
The price is $824
Jun 24 - Jun 25
Total includes taxes and fees
New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym

❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views

9.2 out of 10, Wonderful, (32)
"Spent several days at this wonderful property. Fantastic location!"
$942 nightly
The price is $1,099
Jul 6 - Jul 7
Total includes taxes and fees
❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views

Beachfront Penthouse! 4Bd/3Bth

9.8 out of 10, Exceptional, (18)
"First off, this place was perfect and very spacious for just four of us! My 9yo daughter begged me to take her to see the sunrise, so my wife and i found this place. Its amazing! Our first VRBO! The host was very good, explaining the whole process. We all look forward to staying there again and again!"
$1,185 nightly
The price is $1,382
Jul 1 - Jul 2
Total includes taxes and fees
Beachfront Penthouse! 4Bd/3Bth

Oceanfront 3-BR boardwalk condo w indoor pool!

9.8 out of 10, Exceptional, (31)
"Wonderful place to stay and relax! Great host!"
$698 nightly
The price is $805
Jun 26 - Jun 27
Total includes taxes and fees
Oceanfront 3-BR boardwalk condo w indoor pool!

New Oceanfront 2bd, 2bth / Beach / Pool / Boat

10.0 out of 10, Exceptional, (2)
"I took my sister there for healing and it checked every box. The place was so clean, so comfortable, and so uplifting I knew immediately it was be a place to revisit. This place is top notch…Absolutely loved it!!!"
$665 nightly
The price is $773
Jul 6 - Jul 7
Total includes taxes and fees
New Oceanfront 2bd, 2bth / Beach / Pool / Boat

NEW! Oceanfront Condo / Beach / Pool/Jet Ski /Boat

$651 nightly
The price is $755
Jul 6 - Jul 7
Total includes taxes and fees
NEW! Oceanfront Condo / Beach / Pool/Jet Ski /Boat

NEW! Oceanfront Condo / Beach / Pool/Jet Ski /Boat

$615 nightly
The price is $714
Jul 6 - Jul 7
Total includes taxes and fees
NEW! Oceanfront Condo / Beach / Pool/Jet Ski /Boat

NEW Updated Oceanfront 3bd Beach, Pool, Boat, Fish, #1107

$858 nightly
The price is $1,001
Jun 26 - Jun 27
Total includes taxes and fees
NEW Updated Oceanfront 3bd Beach, Pool, Boat, Fish, #1107

Inviting Virginia Beach Condo w/ Community Pool

8.0 out of 10, Very Good, (8)
"Property was clean and well appointed. Condo staff was helpful and kind. Enjoyed our little weekend trip!"
$894 nightly
The price is $1,022
Jul 13 - Jul 14
Total includes taxes and fees
Inviting Virginia Beach Condo w/ Community Pool

Beach Quarters Resort 4th of 1BR 1BA Oceanfront Sleeps Six

8.8 out of 10, Excellent, (3)
"Beautiful as far as the view, stepped outside directly onto the boardwalk and gorgeous ocean. Pools were very merely looking and not what I imagined but the use of the sister location pool which was right across the street was fantastic and that pool was gorgeous. Owner of the location was easy to get in touch with and very helpful with all of our needs. Location was on the quiet side of the board walk, a little away from all the excitement but was so peaceful."
$285 nightly
The price is $330
Jun 25 - Jun 26
Total includes taxes and fees
Beach Quarters Resort 4th of 1BR 1BA Oceanfront Sleeps Six

Cozy home away from home just minutes from the Beach

9.6 out of 10, Exceptional, (62)
"Quick two day trip but was in a great location that was convenient and had everything you need. Would definitely stay again."
$326 nightly
The price is $377
Jul 15 - Jul 16
Total includes taxes and fees
Cozy home away from home just minutes from the Beach
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

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.
What is there to do in Chesapeake near my condo?
Chesapeake has enough experiences to keep you occupied for weeks (or months!), beginning with Chesapeake Golf Club. Oak Grove Lake Park, Cahoon Plantation Golf Course and Chesapeake Square Mall are other awesome attractions. If you're lingering longer, Greenbrier Mall and Chesapeake Veterans' Memorial are worthwhile additions to your itinerary.