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Aug 8 - Aug 10
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Aug 29 - Aug 31
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Sep 26 - Sep 28

Condo Rentals in Chesapeake

Escape to Your “Virginia Beach Retreat”
Enjoy cooking in this well-equipped kitchen with a microwave, oven, and dishwasher.

Escape to Your “Virginia Beach Retreat”

10.0 out of 10, Exceptional, (37)
"Very clean with a great loacation at a fair price."
Escape to Your “Virginia Beach Retreat”
Historic Condo in the Heart of Downtown Elizabeth City
Cozy living space with a brick wall, wooden beams, and a comfortable sofa.

Historic Condo in the Heart of Downtown Elizabeth City

10.0 out of 10, Exceptional, (21)
"Beautiful Place would love to stay again. Very comfy and cozy. Beds were great!"
Historic Condo in the Heart of Downtown Elizabeth City
VB Oceanfront Condo at Boardwalk. See Dolphins from Balcony. Steps to Beach+Pool
Enjoy the serene beach view from this balcony with a wicker chair and metal railing.

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

2.0 star property
10.0 out of 10, Exceptional, (22)
"One of the nicest oceanside condos we've stayed in."
VB Oceanfront Condo at Boardwalk. See Dolphins from Balcony. Steps to Beach+Pool
Beachfront Condo on the Boardwalk with Ocean Views
Enjoy cooking in this well-lit kitchen with a large window offering a view of the outdoors.

Beachfront Condo on the Boardwalk with Ocean Views

2.0 star property
10.0 out of 10, Exceptional, (15)
"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
Walk to beach BEAUTIFUL 2BR 1BA condo
Enjoy water activities at this resort's pool and slides.

Walk to beach BEAUTIFUL 2BR 1BA condo

10.0 out of 10, Exceptional, (40)
"Everything was perfect. Place was adorable and spotless"
Walk to beach BEAUTIFUL 2BR 1BA condo
Beach Condo 2 Min Walk From The Beach
Guests can stroll along the beach pathway, flanked by railings, to reach the ocean.

Beach Condo 2 Min Walk From The Beach

9.4 out of 10, Exceptional, (112)
"The property had everything we needed. It was quiet at night, close access to the beach, stores, etc. We thoroughly enjoyed our stay there."
Beach Condo 2 Min Walk From The Beach
Great Location ! 1 Short Block To The Boardwalk.
Overlooking the wide beach, this property offers stunning views of the ocean and the city skyline.

Great Location ! 1 Short Block To The Boardwalk.

9.6 out of 10, Exceptional, (254)
"Frank was great and answered any questions I had. Great place!"
Great Location ! 1 Short Block To The Boardwalk.
NEW Updated Oceanfront 3bd Beach, Pool, Boat, Fish, #1107
Relax on the beachfront balcony with two Adirondack chairs and a small table.

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

4.0 out of 10, (1)
The price is ￥96,941
￥162,985 total
includes taxes & fees
Aug 8 - Aug 9
NEW Updated Oceanfront 3bd Beach, Pool, Boat, Fish, #1107
Sojourn's Penthouse 4 BR Sanctuary Condo
Enjoy beach access and stunning ocean views from this beachfront hotel's spacious balconies.

Sojourn's Penthouse 4 BR Sanctuary Condo

8.4 out of 10, Very Good, (5)
"It was beautiful penthouse. So much room for 9 of us. It looks like a fun place for summer vacation. We would consider this house again in the future. "
Sojourn's Penthouse 4 BR Sanctuary Condo
Walk to the Beach and great restaurants! Family-sized condo with balcony.
Relax in style with two Adirondack chairs on a spacious balcony with a sliding glass door leading to the interior.

Walk to the Beach and great restaurants! Family-sized condo with balcony.

10.0 out of 10, Exceptional, (45)
"Our host was very accommodating to any questions or concerns we had. The property was clean and very homey making it easy to stay at. We enjoyed being able to quickly walk to the Convention Center for our event and then to the many restaurants and coffee places in between. "
Walk to the Beach and great restaurants! Family-sized condo with balcony.
A Sea Glass Dream! Modern Decor 1.5 blocks to beach EZ Parking, Fast WiFi!
Relax by the fire pit surrounded by palm trees and ocean views.

A Sea Glass Dream! Modern Decor 1.5 blocks to beach EZ Parking, Fast WiFi!

10.0 out of 10, Exceptional, (58)
"Great location walkable to so many great places to eat and shop. Clean and inviting condo that was perfect for our family vacation! We felt at home. Cindy has the perfect decor touch and the kitchen was stocked with what we needed to cook a few meals in. We loved our stay and hope we get to make it back!"
A Sea Glass Dream! Modern Decor 1.5 blocks to beach EZ Parking, Fast WiFi!
Ocean Sands Resort Oceanfront 1BR Bikes, Aquarium, Chairs
Enjoy breathtaking ocean views from this balcony with comfortable seating for two.

Ocean Sands Resort Oceanfront 1BR Bikes, Aquarium, Chairs

7.0 out of 10, Good, (2)
"Dated, fairly clean. Communication lacking "
Ocean Sands Resort Oceanfront 1BR Bikes, Aquarium, Chairs
Vacationing is easy in this newly refreshed beach condo!
Cozy retreat with a dresser, TV, and potted plant, plus a glass door leading to an outdoor area.

Vacationing is easy in this newly refreshed beach condo!

10.0 out of 10, Exceptional, (33)
"I highly recommend this condo to anyone. Owners were easy to contact, the condo was exceptionally clean and easy access to the beach, shops and restaurants. "
Vacationing is easy in this newly refreshed beach condo!
NEW Updated Oceanfront 2bd 2bth / Beachfront /Pool
On the beach

NEW Updated Oceanfront 2bd 2bth / Beachfront /Pool

9.6 out of 10, Exceptional, (5)
"Beautiful condo. Lovely decor. Location was great, no car needed. Parked the car and rode trollies! A little construction for a few days kinda loud, but that's always expected oceanfront. Great time had by all!"
NEW Updated Oceanfront 2bd 2bth / Beachfront /Pool
Modern Oceanfront Condo + Pool near Top Dining
Stroll along the oceanfront promenade with a clear view of the sea.

Modern Oceanfront Condo + Pool near Top Dining

10.0 out of 10, Exceptional, (2)
"Absoluteley loved our stay. We will come back for sure. The view and location ammenities (pool, kitchen, BBQ) make it much better than an hotel room for that price."
Modern Oceanfront Condo + Pool near Top Dining
Private Virginia Beach Escape w/ Pool & Fire Pit!
Stroll along the gravel path to a secluded seating area surrounded by lush greenery and a tranquil pond.

Private Virginia Beach Escape w/ Pool & Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (2)
"This is among the best stays we’ve ever had in VA Beach! It was the perfect space for my daughter and me (although next time we will bring the rest of the family)! Quiet neighborhood, yet so close to everything we wanted and needed, including Sandbridge beach! The hosts are super friendly and have everything laid out for an easy stay. EVERYTHING was very clean and modern; just as the pictures show! We will always have this place on our list of options to stay when back in VA Beach!"
Private Virginia Beach Escape w/ Pool & Fire Pit!
Relax By the Sea - Charming 1-bedroom condo in superb location near the ocean
Equipped with a coffee maker, microwave, and dishwasher, this kitchen offers a functional layout and essential amenities.

Relax By the Sea - Charming 1-bedroom condo in superb location near the ocean

10.0 out of 10, Exceptional, (4)
"It was wonderful! Very close to everything! The walk to the beach was very short and all the restaurants were great! "
Relax By the Sea - Charming 1-bedroom condo in superb location near the ocean
ON THE BEACH! Stunning Beachfront Property!
Enjoy al fresco dining or relaxation on this deck with a grill and two chairs, overlooking the beach and pier.

ON THE BEACH! Stunning Beachfront Property!

9.8 out of 10, Exceptional, (27)
"Great location with restaurants within walking distance. Would stay here again. "
ON THE BEACH! Stunning Beachfront Property!
Have you ever seen paradise? This one is a beauty! Largest in area
Relax by the pool with a stunning ocean view.

Have you ever seen paradise? This one is a beauty! Largest in area

9.0 out of 10, Wonderful, (23)
"We had a great time! Loved the Sandbridge beach and loved this beach condo. Everything we needed!"
Have you ever seen paradise? This one is a beauty! Largest in area
Oceanfront King Suite with Balcony
Relax by the pool with a view of the city skyline through large windows.

Oceanfront King Suite with Balcony

Oceanfront King Suite with Balcony
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), VA

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

10/10 Excellent
"Great stay. I love it"
Muzammil 3-night trip
Posted 16 hours ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA

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.