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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 496 Condo Rentals in Chesapeake with updated reviews, rates, and availability.

Great Location ! 1 Short Block To The Boardwalk.
Beach nearby, sun loungers

Great Location ! 1 Short Block To The Boardwalk.

9.6 out of 10, Exceptional, (245)
"Quick trip to the beach and the condo was perfect for my family. We were within walking g distance to restaurants, beach/boardwalk. I would definitely stay again and recommend it to other family and friends."
Great Location ! 1 Short Block To The Boardwalk.
Spectacular oceanfront at quiet end of boardwalk at Rudee Inlet SEE SPECIALS.
Lobby

Spectacular oceanfront at quiet end of boardwalk at Rudee Inlet SEE SPECIALS.

9.4 out of 10, Exceptional, (145)
"The place was neat and everything we needed was included. Check in/out was very easy. You can’t beat the location- beachfront with a playground for kids! We would stay here again. "
Spectacular oceanfront at quiet end of boardwalk at Rudee Inlet SEE SPECIALS.
VB Oceanfront Condo at Boardwalk. See Dolphins from Balcony. Steps to Beach+Pool
Property grounds

VB Oceanfront Condo at Boardwalk. See Dolphins from Balcony. Steps to Beach+Pool

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great little place on the beach. Had everything we needed for a wonderful few days away from the cold. "
VB Oceanfront Condo at Boardwalk. See Dolphins from Balcony. Steps to Beach+Pool
Ocean View Condo Steps from the Beach with Fast WiFi & On-Site Pool/Gym
On the beach

Ocean View Condo Steps from the Beach with Fast WiFi & On-Site Pool/Gym

9.4 out of 10, Exceptional, (50)
"Location was perfect for our stay, very nice condo with everything we needed. Thank you!"
Ocean View Condo Steps from the Beach with Fast WiFi & On-Site Pool/Gym
Beachfront Condo on the Boardwalk with Ocean Views
Fridge, microwave, oven, stovetop

Beachfront Condo on the Boardwalk with Ocean Views

2.0 star property
10.0 out of 10, Exceptional, (5)
"It is a great location, a lot of good walkable restaurants. Right on the boardwalk and beach. Very clean."
Beachfront Condo on the Boardwalk with Ocean Views
Dog-Friendly North End Cottage - Oceanside of Atlantic - completely fenced in
Beach nearby, sun loungers

Dog-Friendly North End Cottage - Oceanside of Atlantic - completely fenced in

9.8 out of 10, Exceptional, (236)
"The apartment was perfect for my husband, my mother, our 2 small terriers, and me. Kitchen was well equipped. Beds had memory foam toppers and were very comfortable. Wonderful neighborhood with short walk to beautiful beach! "
Dog-Friendly North End Cottage - Oceanside of Atlantic - completely fenced in
Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!
Fridge, microwave, oven, stovetop

Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!

10.0 out of 10, Exceptional, (333)
"We had a fantastic stay at this cozy, dog-friendly duplex at the North End! The location is unbeatable—just a short walk to the beach, with Cape Henry Lighthouse and First Landing State Park just minutes away. It made for the perfect blend of relaxation and outdoor adventure.The property was exactly as described—clean, well-appointed, and truly welcoming for both people and pups! It’s clear the owners have put thought into every detail, from the comfortable furnishings to the convenient layout....
Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!
NEW Updated! Oceanfront Sanctuary - Sand and Sea
Beach nearby

NEW Updated! Oceanfront Sanctuary - Sand and Sea

2.0 star property
10.0 out of 10, Exceptional, (3)
"We plan this stay last minute. The place was excellent and right on the beach. The place was nice and clean and the communication with the owner was great. The place had everything we needed and we enjoyed our time. "
The price is $628
includes taxes & fees
$541 per night
May 6 - May 7
NEW Updated! Oceanfront Sanctuary - Sand and Sea
Luxury oceanfront condo on the beach with balcony & pools
Property grounds

Luxury oceanfront condo on the beach with balcony & pools

8.6 out of 10, Excellent, (32)
"I can’t say enough about the amazing view of the ocean from this place. I would stay again!"
Luxury oceanfront condo on the beach with balcony & pools
Vacation escape with beach and bay views, pools, & balconies
Exterior

Vacation escape with beach and bay views, pools, & balconies

9.0 out of 10, Wonderful, (19)
"The location was nice and quiet tho we were there off season. It is beach front. There were several pieces of broken/stained furniture. The dresser in the one rooms had 3 broken drawers. There is a crockpot in the kitchen which was nice for us. It also would have been nice to know before booking that we had to go get the key/door passes at a different location. We were in a bus and it wasn’t super convenient to go to the office. Overall nice stay and met our needs. "
Vacation escape with beach and bay views, pools, & balconies
Beachfront Penthouse! 4Bd/3Bth
Beach nearby

Beachfront Penthouse! 4Bd/3Bth

9.8 out of 10, Exceptional, (17)
"This is a beautiful condo with plenty of room for our 5 adults and 6 teenagers. It’s an easy walk to the beach, and the Sandbridge Seaside Market next door was an easy walk for donuts and groceries. There are plenty of chairs and a beach cart in the storage closet. Highly recommend! "
The price is $1,048
includes taxes & fees
$903 per night
May 6 - May 7
Beachfront Penthouse! 4Bd/3Bth
Awesome Beach Getaway! 1 block to the ocean, with a big pool in the back.
Outdoor dining

Awesome Beach Getaway! 1 block to the ocean, with a big pool in the back.

10.0 out of 10, Exceptional, (16)
"This house was in a very nice neighborhood just one block from the beach. I come to VB regularly to visit my Grandson. In the past I'd always stay at hotels. This time I decided to try a VRBO and chose this one based upon its location and reviews. The reviews are spot on! Since my daughter, Grandson, and me stay there, I need 3 separate beds, which this house has, plus 2 bathrooms. Very nice and I hope to stay there again!"
Awesome Beach Getaway! 1 block to the ocean, with a big pool in the back.
3 BLOCKS TO THE BEACH IN THE “VIBE” DISTRICT
Beach nearby, sun loungers, beach towels

3 BLOCKS TO THE BEACH IN THE “VIBE” DISTRICT

10.0 out of 10, Exceptional, (116)
"The place is perfect—clean with a nice kitchen and comfy bed (we only used the King). It was also well stocked with even fruit and cookies!The boardwalk and excellent restaurants are within easy walking distance.There is some major construction nearby, which means driving and walking directions need to adjust. But, far enough away that there is NO noise, so it is not really a problem at all."
3 BLOCKS TO THE BEACH IN THE “VIBE” DISTRICT
Breezy, Quaint, and Dog- Friendly North End duplex.
Exterior

Breezy, Quaint, and Dog- Friendly North End duplex.

10.0 out of 10, Exceptional, (249)
"Perfect place for family and dog! Had a wonderful time "
Breezy, Quaint, and Dog- Friendly North End duplex.
Condo near the beach & pool with 2 balconies & central AC
Exterior

Condo near the beach & pool with 2 balconies & central AC

7.8 out of 10, Good, (16)
"Great place, great location!"
Condo near the beach & pool with 2 balconies & central AC
Bright 3rd-floor courtyard condo with balcony, pools, gym, & AC
Exterior

Bright 3rd-floor courtyard condo with balcony, pools, gym, & AC

9.2 out of 10, Wonderful, (18)
"The location was amazing. The condo is right on the beach and close to a nature preserve which was great for bike riding with the family. The complex is a little confusing and we struggled to find our assingned parking spot, condo and navigate the large facility this could be remidied with better signage. I feel some upgrades to the keys are needed as they use bulky RFID cards and physical keys. The condo was wonderful, clean and well stocked and inviting. Overall i would stay here again as it...
Bright 3rd-floor courtyard condo with balcony, pools, gym, & AC
Sunlit single-level condo with pool, washer/dryer, central AC, & balcony
Fridge, microwave, oven, stovetop

Sunlit single-level condo with pool, washer/dryer, central AC, & balcony

9.6 out of 10, Exceptional, (7)
"My husband and I wanted a winter weekend experiencing walks on the sand and the sound of the surf. The weather didn't quite cooperate but we enjoyed our stay nevertheless. The condo was clean and had everything we could need. My only complaint would be that there wasn't a towel bar in the bathroom for hanging bath towels after showering. Otherwise everything else was excellent."
Sunlit single-level condo with pool, washer/dryer, central AC, & balcony
Sandbridge Beach,Virginia Beach Penthouse Condominum
On the beach

Sandbridge Beach,Virginia Beach Penthouse Condominum

10.0 out of 10, Exceptional, (217)
"Great condo! Great host! Great location!"
Sandbridge Beach,Virginia Beach Penthouse Condominum
Sojourn Southern Dunes Sleeps 6
On the beach

Sojourn Southern Dunes Sleeps 6

10.0 out of 10, Exceptional, (9)
"Our host was awesome any questions we had she responded very quickly. The condo was beautiful very clean and stocked with everything we needed! "
Sojourn Southern Dunes Sleeps 6
Joshua2 on the Boardwalk with Spacious 3 Bedrooms, 2 Bths, Kitchen & Indoor Pool
Marina

Joshua2 on the Boardwalk with Spacious 3 Bedrooms, 2 Bths, Kitchen & Indoor Pool

10.0 out of 10, Exceptional, (86)
"We had a fantastic time at Joshua2! Beautiful condo with beautiful views. Check-in involved a few steps but instructions were very clear and we had no issues. The kitchen had everything we needed, the beds were comfortable, and everything was incredibly clean upon arrival. The only negative was the wi-fi, which was quite spotty, but this didn’t deter from our wonderful experience. "
Joshua2 on the Boardwalk with Spacious 3 Bedrooms, 2 Bths, Kitchen & Indoor Pool
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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Other property types in Chesapeake

The Ocean Key Virginia Beach Resort
Indoor pool

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1317)
"Good overall! Did not realize the pool was on the lobby"
The price is $162
includes taxes & fees
$139 per night
May 13 - May 14
The Ocean Key Virginia Beach Resort
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Exterior

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.0 out of 10, Very Good, (1047)
"very nice place"
The price is $162
includes taxes & fees
$139 per night
May 27 - May 28
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
The Atrium Resort, Virginia Beach by Vacatia
Beach nearby

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very Good, (1324)
"Quick weekend getaway. Hotel for the price was nice. "
The price is $152
includes taxes & fees
$131 per night
May 13 - May 14
The Atrium Resort, Virginia Beach by Vacatia
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.

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.