
Condo holiday 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.

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.

Ocean & Bay Views - Newly Renovated! Local Family!
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 Back Bay views. The condo features a large open-concept living space, and a fully equipped gourmet kitchen, and high end finishes. Free access to all condo amenities, including free parking, 3 pools, grills, and a fitness center! Your beach vacation awaits!

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!

Paradise at the Beach
Our newly renovated condo has all of the comforts of home. Accommodates 6 adults or perfect for families. Bedroom #1 has a KING SUITE, with sliding glass door that leads to the pool. The pool is open from Memorial weekend til the end of September. Bedroom 2 has a Queen size bed and livingroom has a sofabed. Blackout curtains in both bedrooms. Cable TV and Wi-Fi in ALL rooms. Secured building. Outdoor shower and shared grill. Come have a relaxing and fun vacation at the beach.

2 Bedroom Stylish Kingsmill condo
Located in the beautiful Kingsmill resort, this charming two bedrooms, two baths condo with stunning seasonal views over the pond is only a few minutes away from CW, Busch Gardens, water country, William and Maryand other Williamsburg attractions. All Kingsmill amenities are not included as they are strictly for Kingsmill residents Guests have access to the Spa and to the Mill Coffee House which is within walking distance from the condo and serves breakfast and lunch every day..

Cozy 1 Bd condo, 1 block from the beach!
Your family will be close to everything when you stay at this centrally-located, cozy condo. 1 bedroom, 1 bath just a block off the beach. Queen bed in master and pull out couch and futon in living room. (comfortably sleeps 4, could sleep up to 6) Cute, fully equipped kitchen and dining area for 2. Walking distance to the popular board walk and beach, restaurants, bars, shopping and nearby activities and attractions. Perfect for a couples get away or a small family stay!

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 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.

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

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.

Beachfront Getaway, Pet Friendly, Mermaid Suite
Escape to a serene, semi-private beach with breathtaking views and everything you need for the perfect vacation. Welcome to Big Blue, where unforgettable memories await. Beach access, Fully stocked kitchen, modern upgrades, comfy beds, large open floor plan, bbq pit, outdoor patio, beach gear & many personal touches. Condo not suitable for children under 7. Pet fee $100 for max of 2 with approval.

Beach Bungalow on the Boardwalk
If you are looking for convenience, comfort, and a pleasant experience than Beach Bungalow on the Boardwalk is for you. We are located only a block from the beach and boardwalk, and there is no shortage of restaurants and entertainment in the area. Our condo has been completely renovated with all new furniture. We know you will enjoy your experience and look forward to being your host.
Popular amenities for Chesapeake condo rentals
Weekly condo rentals

OBC - 1BR/1BA - Amazing Oceanfront View!

Life’s A Beach

Shadowlawn Villas, Suite III, close to surf park

2BD2BA Condo w/Pool2Blocks2Beach

2BD/2BA Villa across Currituck Beach Lighthouse

River Breeze Condo @ Kingsmill

Paradise Cove

Boardwalk Oceanfront Studio near Top Dining
Pet-friendly condo rentals

2 bdr: Steps to Sand, Dog-Friendly!

Cozy & Fun Hampton Condo, WIFI & W/D! Dogs welcome

Ocean Breeze: New Condo Steps to the Beach

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

Ocean Bliss: Cozy Apt Retreat(D)

OceansideLuxuryCondo*Walk2Beach*Pool*Pets*NoStairs

Oyster & Pearl Beautiful New Single Level Condo

Wonderful & tranquil beach retreat: 2BR/2BA Condo.
Condo rentals with a pool

Sandbridge Beach - DeepSeaSide Retreat

Oceanfront Condo with Spectacular Beach View

Oceanfront Gem VaB Studio Exceptional Views

Off The Hook-Luxury Cottage - Heart of Corolla!

The White Pearl A Modern 3 Bed w/Private Hot Tub!

Beach Studio - Oceanside, Pool, Boardwalk, Bikes

Barefoot Bliss - Single Level Steps to the Beach

Seas The Day of Virginia Beach
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $188 NZD | $188 NZD | $186 NZD | $183 NZD | $179 NZD | $174 NZD | $173 NZD | $176 NZD | $186 NZD | $176 NZD | $185 NZD | $178 NZD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Quick stats about condo rentals in Chesapeake

Total holiday rentals
Explore 40 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $85 NZD per night before taxes and fees

Verified guest reviews
Over 1,000 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesapeake holiday rentals include Wi-Fi access

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

4.8 Average rating
Chesapeake stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square
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- Condo rentals Virginia
- Condo rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Outlook Beach
- Chrysler Museum of Art
- Nauticus
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Town Point Park
- First Landing Beach
- Hampton University
- Currituck Beach Lighthouse
- Old Dominion University
- Currituck Beach
- Chrysler Hall
- Regent University




