Search Condo Rentals in Chesapeake

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 388 Condo Rentals in Chesapeake with updated reviews, rates, and availability.

Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach

9.8 out of 10, Exceptional, (87)
"The condo is a refurbed motel room. Great location. Manager was quick to respond to questions_concerns. Cooking items were dirty and the sponge at the sink wrung out dirty water. Bathroom/shower were nicely redone. "
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach

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

2.0 star property
10.0 out of 10, Exceptional, (8)
"One of the nicest oceanside condos we've stayed in."
VB Oceanfront Condo at Boardwalk. See Dolphins from Balcony. Steps to Beach+Pool

Joshua2 on the Boardwalk-3 Bedrm, 2 Bath, kitchen, indoor Pool

10.0 out of 10, Exceptional, (81)
"I have stayed in a number of VRBO's, and I would have to say that this one was one of the best we have stayed at. Everything was very clean, comfortable, and welcoming from the minute we walked in. The check in process was easy and fast. The front desk staff was very pleasant and helpful. He gave us a lot of information about the area. The condo had everything we needed from the super nice appliances and lots of dishes and cooking equipment, down to the loufas set out in the shower for us to...
Joshua2 on the Boardwalk-3 Bedrm, 2 Bath, kitchen, indoor Pool

New Oceanfront 3Bd / Pool / Fishing / Sunrise

New Oceanfront 3Bd / Pool / Fishing / Sunrise

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

10.0 out of 10, Exceptional, (13)
"The condo was perfect for my family of 4. Close to the beach and restaurants."
Awesome Beach Getaway! 1 block to the ocean, with a big pool in the back.

Beachfront Condo on the Boardwalk with Ocean Views - Sleeps 8

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great and we will be back"
Beachfront Condo on the Boardwalk with Ocean Views - Sleeps 8

Great Location ! 1 Short Block To The Boardwalk.

9.6 out of 10, Exceptional, (236)
"Condo was cute and comfortable. Close to the beach. Our first visit. Frank was great to work with. "
Great Location ! 1 Short Block To The Boardwalk.

New Oceanfront Penhouse 2 Decks! Sunrise / Sunsets

The price is SAR 732
SAR 2,655 total
includes taxes & fees
23 Feb - 24 Feb
New Oceanfront Penhouse 2 Decks! Sunrise / Sunsets

Resort 302C Wilbur 5 minute walk to boardwalk, NO DRIVING REQUIRED,

10.0 out of 10, Exceptional, (31)
"Great spacious property, amazing location to the beach, restaurants, activities. Would come back!"
Resort 302C Wilbur 5 minute walk to boardwalk, NO DRIVING REQUIRED,

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

9.4 out of 10, Exceptional, (48)
"Excellent rental!"
Ocean View Condo Steps from the Beach with Fast WiFi & On-Site Pool/Gym

Beachfront Condo with Ocean Views. Sleeps 6.

9.6 out of 10, Exceptional, (9)
"The place was perfect,we had ocean view and street view. The evening sun poured into the front room to warm up before the sun set. The ocean view was even more dramatic, especially with the full moon. The only thing that could be improved would be the kitchen utensils "
Beachfront Condo with Ocean Views. Sleeps 6.

Enjoy Sunrise and dolphin's swimming every morning from your personal balcony!

10.0 out of 10, Exceptional, (27)
"Host met us upon arrival. Explained all technical stuff. Stocked with essentials and market right across the street. Great stay, lots to do."
Enjoy Sunrise and dolphin's swimming every morning from your personal balcony!

Sandbridge Beach,Virginia Beach Penthouse Condominum

10.0 out of 10, Exceptional, (211)
"What a WONDERFuL PLACE!! Better than advertised. Look forward to staying again."
Sandbridge Beach,Virginia Beach Penthouse Condominum

ON THE BEACH! Stunning Beachfront Property!

9.8 out of 10, Exceptional, (21)
"This house is cut and looks over the ocean."
ON THE BEACH! Stunning Beachfront Property!

Oceanfront & Pool, on the Boardwalk at 37th Street

9.8 out of 10, Exceptional, (169)
"Great location, great host. Had a great holiday celebration. "
Oceanfront & Pool, on the Boardwalk at 37th Street

Sandbridge Beach Condo with fantastic Ocean View and Bay View Balcony!

9.8 out of 10, Exceptional, (113)
"Definitely recommending this spot to others. Great stay for a small family trip. Very secure location"
Sandbridge Beach Condo with fantastic Ocean View and Bay View Balcony!

Enjoy Beautiful Ocean Views from this 2 Bedroom, 2.5 Bath Oceanfront Condo!

9.8 out of 10, Exceptional, (61)
"It is located in the heart of Virginia Beach with access to all little charming restaurants and shops. There is a straight shot to the highway towards Norfolk. And you cannot beat the ocean view. Wonderful place"
Enjoy Beautiful Ocean Views from this 2 Bedroom, 2.5 Bath Oceanfront Condo!

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

10.0 out of 10, Exceptional, (332)
"This is a dog-friendly beach cottage that you cannot tell is dog friendly because it’s immaculately clean and well maintained. It has everything you need to make it a comfortable stay and Angie is a fantastic host. We will definitely be back. It was the perfect location for visiting my family. "
Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!

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

10.0 out of 10, Exceptional, (248)
"We enjoyed our week long stay here as the host/guest provided easy check-in/out instructions and provided everything we needed for our stay. We really enjoyed our stay. My only disappointment (minor) is I wish the cost was slightly less during the winter as the VB area is not visited much during winter months. Other than that, great stay and experience. "
Breezy, Quaint, and Dog- Friendly North End duplex.

Beach condo with pool views, balcony, outdoor pool & gym

8.0 out of 10, Very Good, (25)
"From the pictures it pookas though it's a 3 bed room but it's only 2 .Also I thought it was more close to the Ocean front strip. If planning to Vaca at this location please have your own transportation. The location is far from any restaurants and stores and we weren't able to get a lift nor Uber and taxi companies said they do not service this area ..Other than the place was very comfortable and very nice for a quiet getaway!!"
Beach condo with pool views, balcony, outdoor pool & gym
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.
Don't see what you're looking for?
See all available properties in Chesapeake
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chesapeake

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1290)
"Been here 3 times now and every time the staff is always helpful and just super nice. Overall just a really good team "
The price is SAR 273
SAR 537 total
includes taxes & fees
12 Mar - 13 Mar
The Ocean Key Virginia Beach Resort

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.0 out of 10, Very Good, (1437)
"Great place but need more bigger park spaces for guess"
The price is SAR 387
SAR 668 total
includes taxes & fees
23 Feb - 24 Feb
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

9.8 out of 10, Exceptional, (98)
"Our family of 4 enjoyed a quiet time in the outer banks at this lovely beach house. November isn't exactly the time most folks visit the beach, but we've spent most of our lives in the far north, so the "chilly weather" didn't prevent us from enjoying kayaking in the inner channels and viewing the sunset from the crow's nest. We found the kitchen very adequate; we were able to cook a lovely thanksgiving dinner and ate quite well the entire time. We packed all our needs/food for the weekend so...
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
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?
Expedia makes it a cinch to find your ideal condo in Chesapeake. Looking for a luxury escape? Take advantage of our filters to search for properties that have a 5-star rating. If you’re sticking to a budget, select how much you want to spend and then browse our amazing options. We’ll help you find the perfect pad whatever your getaway looks like.
How can I find cheap condos in Chesapeake?
Expedia can help you narrow your search for cheap condos in Chesapeake. To find a superb stay in a couple of quick clicks, try out our handy filter tool to tailor your search results by amenities, star rating and budget.