A golf course, a large building complex, and a marina by a river.

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Chesapeake condo rentals

A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

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

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
9.0 out of 10, Wonderful, (2 reviews)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is CA $200
CA $262 total
includes taxes & fees
Nov 15 - Nov 16
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

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

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Chesapeake
8.0 out of 10, Very good, (5 reviews)
"Good location and spacious rooms. Good stay!"
United States
Ariel G.
The price is CA $223
CA $294 total
includes taxes & fees
Nov 1 - Nov 2
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

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

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Chesapeake
The price is CA $201
CA $263 total
includes taxes & fees
Nov 1 - Nov 2
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

4. Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!

Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
Chesapeake
9.4 out of 10, Exceptional, (8 reviews)
"The condo is nice, clean and very roomy. We love the stay and very convenient. The hotel provides breakfast it’s great!!"
United States
Linh T.
The price is CA $380
CA $501 total
includes taxes & fees
Nov 15 - Nov 16
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
A beachfront hotel with multiple buildings, a sandy beach, and a body of water.

5. New! 3Bd 2Bth Oceanfront / Pool / Gym / Beach

New! 3Bd 2Bth Oceanfront / Pool / Gym / Beach
Sandbridge
10.0 out of 10, Exceptional, (6 reviews)
"Successful vacation."
United States
Shawn F.
The price is CA $205
CA $840 total
includes taxes & fees
Oct 26 - Oct 27
New! 3Bd 2Bth Oceanfront / Pool / Gym / Beach
A living room with two sofas, a coffee table, and a kitchen in the background.

6. Playa Sin Olas - Virginia Beach - Walk To Beach - Family Friendly

Playa Sin Olas - Virginia Beach - Walk To Beach - Family Friendly
Northeast Virginia Beach
The price is CA $214
CA $525 total
includes taxes & fees
Nov 3 - Nov 4
Playa Sin Olas - Virginia Beach - Walk To Beach - Family Friendly
A building labeled "Ocean Sands Resort" with a view of the ocean and sunset.

7. High floor, Ocean View Condo

High floor, Ocean View Condo
Northeast Virginia Beach
The price is CA $252
CA $427 total
includes taxes & fees
Oct 22 - Oct 23
High floor, Ocean View Condo
A beachfront hotel with multiple-story buildings, a sandy beach, and a view of the ocean and marshy areas.

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

New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym
Sandbridge
8.6 out of 10, Excellent, (11 reviews)
"Property was very clean and exactly as the ad described. The host gave detailed instructions on parking and how to access the condo and was very easy to reach if I had questions. The large balcony was a great space to have coffee in the morning and listen to birds while looking over the back bay and the sunsets were spectacular. Would highly recommend this booking"
United States
Michelle K.
The price is CA $307
CA $868 total
includes taxes & fees
Oct 25 - Oct 26
New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym
A modern living room with a grey sectional sofa, a flat-screen TV, a fireplace, and a ceiling fan.

9. Vibe District, Atlantic Surf Park, VB Sports Center, Boardwalk & Oceanfront

Vibe District, Atlantic Surf Park, VB Sports Center, Boardwalk & Oceanfront
Northeast Virginia Beach
9.6 out of 10, Exceptional, (5 reviews)
"Place was great, but if you’re not physically able to go up steps this place is not for you."
United States
Jim W.
The price is CA $281
CA $612 total
includes taxes & fees
Nov 3 - Nov 4
Vibe District, Atlantic Surf Park, VB Sports Center, Boardwalk & Oceanfront
A bedroom with a large bed, a view of the balcony, and a sliding glass door.

10. Beachfront Penthouse! 4Bd/3Bth

Beachfront Penthouse! 4Bd/3Bth
Sandbridge
9.0 out of 10, Wonderful, (30 reviews)
"Proximity to the ocean was great."
United States
Raymond J.
The price is CA $462
CA $1,251 total
includes taxes & fees
Oct 26 - Oct 27
Beachfront Penthouse! 4Bd/3Bth
The perfect poolside escape with sun loungers and calm vibes.

11. NEW! Oceanfront Triton`s Treasure 3 Bd / Pool/ Gym

NEW! Oceanfront Triton`s Treasure 3 Bd / Pool/ Gym
Sandbridge
9.2 out of 10, Wonderful, (14 reviews)
"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 CA $302
CA $897 total
includes taxes & fees
Oct 25 - Oct 26
NEW! Oceanfront Triton`s Treasure 3 Bd / Pool/ Gym
A beachside boardwalk with a water play area, palm trees, and beach chairs.

12. Oceanfront Beach Condo, Pool, Gym, Fishing Surfing

Oceanfront Beach Condo, Pool, Gym, Fishing Surfing
Northeast Virginia Beach
9.2 out of 10, Wonderful, (10 reviews)
"Great stay. Great Host"
United States
Dominique
The price is CA $353
CA $860 total
includes taxes & fees
Oct 22 - Oct 23
Oceanfront Beach Condo, Pool, Gym, Fishing Surfing
A modern living room with a large window overlooking the ocean, a flat-screen TV, a sofa, a coffee table, and a small side table.

13. Oceanfront Condo/ Pool/ Surfing/ Fishing / EW 1002

Oceanfront Condo/ Pool/ Surfing/ Fishing / EW 1002
Northeast Virginia Beach
9.0 out of 10, Wonderful, (2 reviews)
"The views of the ocean at sunrise were stunning. The host was very responsive and helpful. We would stsy there again. "
United States
S T.
The price is CA $378
CA $983 total
includes taxes & fees
Oct 25 - Oct 26
Oceanfront Condo/ Pool/ Surfing/ Fishing / EW 1002
At the center is a massive turquoise wave pool designed for surfing, with perfectly formed waves rolling along a long central divider.

14. New! Beachfront 3bd / 2Bth/Pool 104A

New! Beachfront 3bd / 2Bth/Pool 104A
Sandbridge
9.8 out of 10, Exceptional, (6 reviews)
"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 CA $376
CA $997 total
includes taxes & fees
Nov 3 - Nov 4
New! Beachfront 3bd / 2Bth/Pool 104A
A beachside water park with a blue pool area, palm trees, and a sandy beach in the background.

15. Oceanfront Condo, Heated Pool, Fitness Center

Oceanfront Condo, Heated Pool, Fitness Center
Northeast Virginia Beach
10.0 out of 10, Exceptional, (5 reviews)
"Everything was clean and comfortable. Our host responded within minutes when we reached out. The views were spectacular. Within walking distance to lots of shops and restaurants. Had a fantastic time and look forward to visiting again. "
United States
Randi C.
The price is CA $483
CA $990 total
includes taxes & fees
Oct 22 - Oct 23
Oceanfront Condo, Heated Pool, Fitness Center
A beachfront hotel with colorful buildings, a swimming pool, and a beach area with umbrellas and people.

16. New Oceanfront Penthouse | 2 Decks | Gym, Pool 418

New Oceanfront Penthouse | 2 Decks | Gym, Pool 418
Sandbridge
7.0 out of 10, Good, (2 reviews)
"We enjoyed our stay at the property. The only thing is the beds were not comfortable and felt like worn out mattresses, except the bed in master bedroom. Besides that our experience was comfortable with nice sunset views and clean property close to the beach"
United States
vishakha r.
The price is CA $582
CA $1,264 total
includes taxes & fees
Oct 27 - Oct 28
New Oceanfront Penthouse | 2 Decks | Gym, Pool 418
A bedroom with two bunk beds, a bedside table with a lamp, and a dresser.

17. Direct Beach Access/Oceanfront Condo/Family Friendly

Direct Beach Access/Oceanfront Condo/Family Friendly
Northeast Virginia Beach
The price is CA $563
CA $1,057 total
includes taxes & fees
Oct 22 - Oct 23
Direct Beach Access/Oceanfront Condo/Family Friendly
Wave park

18. Oceanfront Beach Condo, Pool, Gym, Fishing Surfing

Oceanfront Beach Condo, Pool, Gym, Fishing Surfing
Northeast Virginia Beach
9.6 out of 10, Exceptional, (13 reviews)
"The place was as-described and perfect for our family of 5. I really appreciated the ease of check-in and check-out, the great communication, and cleanliness. I would stay here again!"
United States
Leah S.
The price is CA $352
CA $845 total
includes taxes & fees
Oct 22 - Oct 23
Oceanfront Beach Condo, Pool, Gym, Fishing Surfing
A living room with a balcony overlooking the ocean, a beige sofa, and three beach-themed wall art pieces.

19. Oceanfront Beach Condo, Pool, Gym, Fishing Surfing

Oceanfront Beach Condo, Pool, Gym, Fishing Surfing
Northeast Virginia Beach
10.0 out of 10, Exceptional, (2 reviews)
"It was wonderful staying in this beautiful 2-bedroom, 2-bathroom oceanfront unit right on the boardwalk! The place was clean, comfortable, and felt like a perfect home away from home while visiting Virginia Beach.I loved how walkable the location was to the pier, restaurants, and everything we wanted to enjoy. We had some delicious seafood at Mahi’s and Waterman’s Surfside Grille, which were both great choices!Since it was just me and my friend staying, we really appreciated having a comfortable...
United States
Tisha W.
The price is CA $397
CA $906 total
includes taxes & fees
Oct 22 - Oct 23
Oceanfront Beach Condo, Pool, Gym, Fishing Surfing
A balcony with a view of the beach, a dining area with a table and chairs, and a wall-mounted macrame piece.

20. Oceanfront Beach Condo, Pool, Gym, Fishing Surfing

Oceanfront Beach Condo, Pool, Gym, Fishing Surfing
Northeast Virginia Beach
8.4 out of 10, Very good, (8 reviews)
"Excellent experience here! Host was fantastic! Condo was clean and bright. Communication was clear and timely."
United States
Jill J.
The price is CA $393
CA $824 total
includes taxes & fees
Oct 22 - Oct 23
Oceanfront Beach Condo, Pool, Gym, Fishing Surfing
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.
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Top Chesapeake Hotel Reviews

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

8/10 Good
"The lady in the front was nice and the hotel was beautiful but one of the black maintenance/room service ladies was extremely rude, would give it a 5 if it wasn’t for her"
Isaac 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Find out more about Chesapeake

Chesapeake Condo Rentals information

Number of reviews
57
Accommodation
438 Condo Rentals
Lowest Price
CA $262
Highest Price
CA $1,316

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?
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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.

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