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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Featured Condo Rentals in Chesapeake and around

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

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

10.0 out of 10, Exceptional, (1)
"Very clean , great location. Will stay there again!!!"
The price is €160
includes taxes & fees
2 Nov - 3 Nov
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Indoor pool

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

2.5 star property
8.0 out of 10, Very good, (4)
"Perfect for what we needed for one day layover before outer Banks"
The price is €171
includes taxes & fees
2 Nov - 3 Nov
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Dining

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

The price is €158
includes taxes & fees
2 Nov - 3 Nov
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
NEW Updated! Oceanfront Sanctuary - Sand and Sea
Beach nearby

NEW Updated! Oceanfront Sanctuary - Sand and Sea

2.0 star property
9.8 out of 10, Exceptional, (9)
"We had a great stay. Unit was spacious, well appointed and decorated. Our family of 4 were very comfortable. Access to the beach a breeze. Nice location away from the touristy boardwalk. "
NEW Updated! Oceanfront Sanctuary - Sand and Sea
New Oceanfront Penhouse 2 Decks! Sunrise / Sunsets
Terrace/patio

New Oceanfront Penhouse 2 Decks! Sunrise / Sunsets

10.0 out of 10, Exceptional, (2)
"Property was perfect for families (lots of space), right on the beach, and had an elevator. I had a family member with limited mobility, and the condo was perfect."
New Oceanfront Penhouse 2 Decks! Sunrise / Sunsets
New! 3Bd 2Bth Oceanfront / Pool / Gym / Beach
Beach nearby

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

10.0 out of 10, Exceptional, (1)
"We had an amazing stay at this beautiful Sandbridge condo! The space was spotless, fully stocked with everything we needed, and made us feel right at home from the moment we walked in. There was plenty of room for our group of four to relax comfortably. The location was ideal—peaceful yet close to everything. Communication with the host was excellent—friendly, responsive, and helpful every step of the way. We couldn’t have asked for a better experience and would absolutely stay here again!"
The price is €557
includes taxes & fees
7 Oct - 8 Oct
New! 3Bd 2Bth Oceanfront / Pool / Gym / Beach
New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym
Beach nearby

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

9.6 out of 10, Exceptional, (4)
"We attended a wedding and this place was the perfect location just across the street from the venue. There was another car parked in our reserved spot that made it difficult to get the key fob and return it but other than that it was a great place to stay. "
The price is €544
includes taxes & fees
7 Oct - 8 Oct
New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym
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, (38)
"Lovely condo close with a short walk to the beach. We had a great time and will definitely stay again!"
The price is €480
includes taxes & fees
5 Nov - 6 Nov
Awesome Beach Getaway! 1 block to the ocean, with a big pool in the back.
Waterfront Penthouse! 4bd/4Bth, 3000 sqft, 2 Decks
Property grounds

Waterfront Penthouse! 4bd/4Bth, 3000 sqft, 2 Decks

9.6 out of 10, Exceptional, (18)
"A beautiful weekend getaway with family at Sandbridge! Plenty of space for each family member, furnishings were spot on! Condo complex just opening for season; pools not open yet. Strongly recommend for group or family with lots of interests."
Waterfront Penthouse! 4bd/4Bth, 3000 sqft, 2 Decks
❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views
Terrace/patio

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

9.2 out of 10, Wonderful, (35)
"Our stay was amazing and the host was excellent. This was the best stay I have had on any vacation. Thank you for perfection "
The price is €607
includes taxes & fees
7 Oct - 8 Oct
❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views
New! Beachfront 3bd / 2Bth/Pool/Hot tub 104A
Beach nearby

New! Beachfront 3bd / 2Bth/Pool/Hot tub 104A

10.0 out of 10, Exceptional, (1)
"Property was exceptional. The kitchen was equipped with all new appliances. There was cooking pots and pans for everything you might want to cook. Washer and dryer new Maytags and the TVs were extremely large and in living room and every bedroom. I do wish there had been a walk-in shower on one of the bathrooms as we are elderly and unable to use the big high tubs. What really made the property so exceptional was the view of the water and how close to the beach the unit is. Just fantastic....
New! Beachfront 3bd / 2Bth/Pool/Hot tub 104A
Beachfront Penthouse! 4Bd/3Bth
Beach nearby

Beachfront Penthouse! 4Bd/3Bth

9.4 out of 10, Exceptional, (23)
"Great place and very convenient to the beach. Loved the security with all of the locking gates and elevators. Would definitely recommend staying here. "
The price is €817
includes taxes & fees
7 Oct - 8 Oct
Beachfront Penthouse! 4Bd/3Bth
New Oceanfront 2bd, 2bth / Beach / Pool / Boat
2 bedrooms, iron/ironing board, WiFi, bed sheets

New Oceanfront 2bd, 2bth / Beach / Pool / Boat

10.0 out of 10, Exceptional, (3)
"This was a very clean and perfect location especially if you have kids. An amazing playground Nextdoor on the beach! Highly reccommend"
New Oceanfront 2bd, 2bth / Beach / Pool / Boat
Cozy home away from home just minutes from the Beach
Beach nearby, beach towels

Cozy home away from home just minutes from the Beach

9.6 out of 10, Exceptional, (65)
"Great location"
The price is €238
includes taxes & fees
3 Nov - 4 Nov
Cozy home away from home just minutes from the Beach
Cozy 3-bedroom condo with AC and WiFi in charming Virginia Beach
Fridge, microwave, oven, stovetop

Cozy 3-bedroom condo with AC and WiFi in charming Virginia Beach

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great location , with restaurant across the street Amy family and I enjoyed our stay "
The price is €877
includes taxes & fees
8 Oct - 9 Oct
Cozy 3-bedroom condo with AC and WiFi in charming Virginia Beach
High floor, Ocean View Condo
Beach nearby

High floor, Ocean View Condo

The price is €265
includes taxes & fees
7 Oct - 8 Oct
High floor, Ocean View Condo
Oceanfront 3-BR boardwalk condo w indoor pool!
Indoor pool, a heated pool

Oceanfront 3-BR boardwalk condo w indoor pool!

9.6 out of 10, Exceptional, (35)
"Wonderful place to stay and relax! Great host!"
The price is €444
includes taxes & fees
13 Oct - 14 Oct
Oceanfront 3-BR boardwalk condo w indoor pool!
Virginia Beach, oceanfront, boardwalk, beach, fun, dolphins
On the beach, sun-loungers

Virginia Beach, oceanfront, boardwalk, beach, fun, dolphins

8.8 out of 10, Excellent, (17)
"The condo is in a great location on the beach. Easy walk to many restaurants and bars on the boardwalk."
The price is €541
includes taxes & fees
20 Oct - 21 Oct
Virginia Beach, oceanfront, boardwalk, beach, fun, dolphins
Mountain Jade Garden Condo Resort 2 bed 2 bath near Newport News City Center
Smart TV

Mountain Jade Garden Condo Resort 2 bed 2 bath near Newport News City Center

3.0 star property
6.0 out of 10, (3)
"Everything was clean and beautiful "
The price is €338
includes taxes & fees
7 Oct - 8 Oct
Mountain Jade Garden Condo Resort 2 bed 2 bath near Newport News City Center
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
On the beach, beach towels

OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission

8.0 out of 10, Very good, (15)
"Loved the location and the avtivitoes/events in the neighborhood."
The price is €665
includes taxes & fees
7 Oct - 8 Oct
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
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
"The staff was very friendly. Decor was great. Loved the bathroom in the room. Very clean would highly recommend. Breakfast was amazing. Also was the first time ever that received an email welcoming us to the hotel before arriving. "
Dianna 2-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA

Find out more about Chesapeake

Find out more about Chesapeake

Chesapeake Condo Rentals information

Number of reviews
240
Accommodation
488 Condo Rentals
Lowest Price
€158
Highest Price
€877

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia