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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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. Great for Business Travelers!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Chesapeake
The price is €176
includes taxes & fees
24 Sept - 25 Sept
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.

2. 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 €176
includes taxes & fees
24 Sept - 25 Sept
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.

3. 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 €188
includes taxes & fees
24 Sept - 25 Sept
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.

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 €276
includes taxes & fees
4 Oct - 5 Oct
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
A compact kitchen with a central island, wooden stools, and a dining area with orange tablecloths.

5. Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home

Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home
Northeast Virginia Beach
9.2 out of 10, Wonderful, (30 reviews)
"It was a very nice and clean place. My only quibble was the exorbitant fee for the property for such a late arrival and early departure time."
United States
Joanne E.
The price is €341
includes taxes & fees
24 Sept - 25 Sept
Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home
A living room with a large window, a sofa, a coffee table, and a TV.

6. Sunset Bay- Gorgeous Bay and Sunset Views.

Sunset Bay- Gorgeous Bay and Sunset Views.
Sandbridge
10.0 out of 10, Exceptional, (11 reviews)
"Very clean, well kept and updated!"
United States
Corey H.
Sunset Bay- Gorgeous Bay and Sunset Views.
A fireplace with a TV mounted above it, a Buddha statue, and a shelf with candles and a camera.

7. Cozy 1-bedroom condo in Hampton/AC NASA ,Air Force ,Army base Hampton U Norfolk

Cozy 1-bedroom condo in Hampton/AC NASA ,Air Force ,Army base Hampton U Norfolk
Hampton
The price is €245
includes taxes & fees
12 Sept - 13 Sept
Cozy 1-bedroom condo in Hampton/AC NASA ,Air Force ,Army base Hampton U Norfolk
A pier extending into the ocean at sunset.

8. Cozy home away from home just minutes from the Beach

Cozy home away from home just minutes from the Beach
Northeast Virginia Beach
9.6 out of 10, Exceptional, (78 reviews)
"the host was so accommodating and helpful. i would absolutely stay here again!!"
United States
Allyson T.
Cozy home away from home just minutes from the Beach
A living room with two sofas, a coffee table, and a kitchen in the background.

9. 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 €337
includes taxes & fees
6 Oct - 7 Oct
Playa Sin Olas - Virginia Beach - Walk To Beach - Family Friendly
A balcony with turquoise Adirondack chairs and a view of a parking lot and buildings.

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

❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views
Sandbridge
9.0 out of 10, Wonderful, (39 reviews)
"Excellent host! "
United States
Cindy S.
❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views
A building labeled "Ocean Sands Resort" with a view of the ocean and sunset.

11. High floor, Ocean View Condo

High floor, Ocean View Condo
Northeast Virginia Beach
High floor, Ocean View Condo
A bedroom with a large bed, a view of the balcony, and a sliding glass door.

12. Beachfront Penthouse! 4Bd/3Bth

Beachfront Penthouse! 4Bd/3Bth
Sandbridge
9.2 out of 10, Wonderful, (28 reviews)
"Proximity to the ocean was great."
United States
Raymond J.
Beachfront Penthouse! 4Bd/3Bth
A modern living room with a grey sectional sofa, a flat-screen TV, a fireplace, and a ceiling fan.

13. 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, (4 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 €414
includes taxes & fees
11 Oct - 12 Oct
Vibe District, Atlantic Surf Park, VB Sports Center, Boardwalk & Oceanfront

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

NEW! Oceanfront Triton`s Treasure 3 Bd / Pool/ Gym
Sandbridge
9.0 out of 10, Wonderful, (9 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 €666
includes taxes & fees
13 Sept - 14 Sept
NEW! Oceanfront Triton`s Treasure 3 Bd / Pool/ Gym
A beachfront hotel with multiple-story buildings, a sandy beach, and a view of the ocean and marshy areas.

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

New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym
Sandbridge
9.0 out of 10, Wonderful, (8 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 €716
includes taxes & fees
13 Sept - 14 Sept
New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym

16. 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.
New! Beachfront 3bd / 2Bth/Pool 104A
A beachside water park with a blue pool area, palm trees, and a sandy beach in the background.

17. Oceanfront Condo, Heated Pool, Fitness Center

Oceanfront Condo, Heated Pool, Fitness Center
Northeast Virginia Beach
10.0 out of 10, Exceptional, (4 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.
Oceanfront Condo, Heated Pool, Fitness Center
A beachside boardwalk with a water play area, palm trees, and beach chairs.

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

Oceanfront Beach Condo, Pool, Gym, Fishing Surfing
Northeast Virginia Beach
9.6 out of 10, Exceptional, (8 reviews)
"The condo was clean, had a great location, and a beautiful view of the ocean. "
United States
Judy H.
Oceanfront Beach Condo, Pool, Gym, Fishing Surfing

19. Coastal Living Luxury Oceanfront Condo, Pool Beach

Coastal Living Luxury Oceanfront Condo, Pool Beach
Northeast Virginia Beach
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful well maintained place, very clean and organized. The host was very responsive and even offered suggestions for dining. Would definitely stay here again."
United States
Julie P.
Coastal Living Luxury Oceanfront Condo, Pool Beach
A covered outdoor area with a view of the sunset over the ocean, featuring a railing and several Adirondack chairs.

20. Luxe Bayfront Retreat | Wraparound Porch

Luxe Bayfront Retreat | Wraparound Porch
Sandbridge
7.0 out of 10, Good, (2 reviews)
"Great stay - Fantastic property while visiting Sandbridge with your family."
United States
Wesley E.
The price is €972
includes taxes & fees
4 Oct - 5 Oct
Luxe Bayfront Retreat | Wraparound Porch
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

Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

10/10 Excellent
"X"
linda 3-night trip
Posted 1 hour ago
Holiday Inn & Suites Virginia Beach North Beach by IHG

Find out more about Chesapeake

Chesapeake Condo Rentals information

Number of reviews
236
Accommodation
439 Condo Rentals
Lowest Price
€176
Highest Price
€972

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.