
Condo vacation rentals in Chesapeake
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Top-rated condo rentals in Chesapeake
Guests agree: these condos are highly rated for location, cleanliness, and more.

Tropical 2BR Condo Getaway 1 Block from the Beach!
Unwind at this gorgeous fully renovated getaway for your family and friends! This two bedroom, one bath beach home is one block from the ocean. This unit accommodates up to 4 adults. Each room is equipped with a smart TV and internet is provided. Our kitchen provides refrigerator, microwave, oven, dishwasher, toaster, Keurig, dishes, cutlery, bowls, pots and pans, and much more! Steps away from shopping and restaurants! This highly sought after vacation spot really is a home away from home.

2 Bedroom Beach Condo Block Off Boardwalk
Come enjoy everything Virginia Beach has to offer. Our newly renovated condo has all of the comforts of home and accommodates 6 adults or perfect for families. Bedroom 1 has a king size bed, bedroom 2 has a queen size bed, and Living room has sofa that pulls out into a full size sofa bed. TVs in all rooms. The Boardwalk, Shopping, Restaurants, and many more activities are all within walking distance. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach.

Ocean & Bay Views - Local Family Owned & Operated
Just steps away from the sand, "Carolina on My Mind" is a 2b/2ba oceanside condo at the exclusive Sanctuary at False Cape, the only Oceanfront complex at Sandbridge in Virginia Beach. You'll enjoy a private patio with both Ocean and Bay views and you'll have access to all the exclusive amenities of the complex. The condo features a large open-concept living space and a fully equipped gourmet kitchen. The master has a king bed, the second bedroom has king bed w/ twin loft. Queen sleeper sofa.

Ocean Escape
Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Community pool area, complete with Jacuzzi tub, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

Luxury Riverfront Condo w/ sunrise & sunset views
Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.

Spacious Captain’s Beach Suite Near Rudee Inlet
Take advantage of the seasonal rates plan a winter escape to the beach! Don’t miss all the wonderful holiday activities to include the holiday lights, holiday parade & more! This spacious beautifully decorated 2-bedroom (each with ensuite baths) condo is near Rudee Inlet and all oceanfront activities. Walk across the street & relax on the beach, dine at great restaurants, walk under the bridge next to the city parking lot to enjoy all the water activities that originate from Rudee Inlet.

2 bedroom condo with oceanfront one block away!
Come enjoy everything Virginia Beach has to offer. Our cozy condo has all of the comforts of home and is perfect for families and accommodates 6 adults. Bedroom 1 has a king size bed w/TV, bedroom 2 has a queen size bed w/TV and the living room has a sofa that pulls out into a full size sofa bed w/TV. The Boardwalk, Shopping, Restaurants, and many more activities are all within walking distance. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach!

Oceanfront Gem VaB Studio Exceptional Views
Newly renovated modern studio condo, owners personal getaway now open to guests. This corner unit, the largest and most private in Oceans ll Condominium complex, is on the 3rd floor and offers beautiful, expansive views at both sunrise and sunset. Just off the boardwalk with community pool, this unit sleeps three. Right on the oceanfront, you won't find a more peaceful getaway! Beach chairs and towels provided. Please note: due to the open layout of the building, there is no elevator.

Oceanfront Studio: Boardwalk, Beach, & Pool Views
Atlantic Ocean views from the comfort of an Oceanfront studio, perfect for beach-loving travelers. Reserved parking space just steps from the beach, indulge in the sand & surf without having to cross a street. Park your car, & let your toes sink into the sand for a truly relaxing stay. Equipped with Wi-Fi & Roku TV, you can stay connected throughout your visit. Take a refreshing dip in the saltwater pool or lounge on the lawn just steps from the beach.

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen
Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family

Cozy & Fun Hampton Condo ~ WIFI & W/D!
Step inside our stylish and cozy space, thoughtfully decorated to make you feel right at home. The fully equipped kitchen has everything you need to cook and dine with ease, while blazing fast WiFi (200 Mbps) keeps you connected for work or entertainment. Enjoy the added convenience of an in-unit washer and dryer, making longer stays effortless. Relax in a peaceful setting while still being close to everything Hampton has to offer.

2 Bedroom Condo ONE Block from the Oceanfront
Come enjoy a Virginia Beach vacation ONE block from the oceanfront and boardwalk. Our 2 bedroom condo accommodates 4 adults and is also perfect for families. Bedroom 1 has a queen size bed and bedroom 2 has a king size bed. There is also a pull out sofa bed in the living room. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do for the whole family.
Popular amenities for Chesapeake condo rentals
Weekly condo rentals

Private Luxe Beach Condo

Sandbridge Beach - DeepSeaSide Retreat

1 Block to Oceanfront & Boardwalk

2BD2BA Condo w/Pool2Blocks2Beach

Marriott's Manor Club Ford's Colony 2BD Villa Slee

1-Bedroom Condo in Williamsburg, VA

Historic Powhatan resort 2 bdrm

Seas The Day of Virginia Beach
Pet-friendly condo rentals

2 bdr: Steps to Sand, Dog-Friendly!

Ocean Breeze: New Condo Steps to the Beach

Walk to beach lovely 2/2 in "Kingsmill on James"

Ocean Bliss: Cozy Apt Retreat(D)

Enjoy Sea Life! Steps to the Beach!

Beachfront Getaway, Pet Friendly, Dolphin Suite

Wonderful & tranquil beach retreat: 2BR/2BA Condo.

The White Pearl A Modern 3 Bed w/Private Hot Tub!
Condo rentals with a pool

*New*Oceanview, Golf, Pool, Tennis, Beach Access

3 Bedroom Suite in Historic Williamsburg!

Great family vacation resort condo. Sleeps 12.

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Charming 1BR Colonial Condo at Wyndham Kingsgate

Coastal Beach condo-amazing view and indoor pool

1br Colonial in Williamsburg -Fun by Busch Gardens

Beach Studio - Oceanside, Pool, Boardwalk, Bikes
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $110 | $110 | $109 | $107 | $105 | $102 | $101 | $103 | $109 | $111 | $125 | $111 |
| Avg. temp | 42°F | 44°F | 51°F | 60°F | 68°F | 77°F | 81°F | 79°F | 74°F | 64°F | 53°F | 46°F |
Quick stats about condo rentals in Chesapeake

Total vacation rentals
Explore 30 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at $50 per night before taxes and fees

Verified guest reviews
Over 890 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesapeake vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesapeake rentals

4.7 Average rating
Chesapeake stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square
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