
Condo holiday rentals in Chesapeake
Find and book unique condos on Airbnb
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 $87 NZD per night before taxes and fees

Verified guest reviews
Over 1,070 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 Cinema Cafe-Greenbrier Mall
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 Condo One Block from the Oceanfront!
Our newly renovated 2 bedroom condo ONE block from the boardwalk accommodates 6 people and is also perfect for families. Each bedroom has a flat screen TV; one with a queen bed and the other with a king bed. There is also a pull out sofa bed in the living room along with a large TV. This is a 2nd floor unit with one designated parking spot. Plenty to do for the whole family with the beach, boardwalk, shopping, restaurants, amusement parks, and many more activities all within walking distance.

Oceanfront Loft: Free Parking & 1 Block from Beach
Welcome to your stylish coastal retreat at the Virginia Beach Oceanfront, a thoughtfully designed 285 sq. ft. one-bedroom apartment just steps from the beach, boardwalk, dining, entertainment, and everything that makes Virginia Beach one of the East Coast’s favorite vacation destinations. This bright and modern condo combines comfort, convenience, and an unbeatable location in the heart of Virginia Beach Oceanfront. "Guest Favorite" for those looking for an easy, relaxing VA Beach getaway.

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!

Condo living just steps from the sand
Come see what Virginia Beach has to offer. Our newly renovated condo has all of the comforts of home and accommodates 4 adults or perfect for families of 5. Bedroom 1 has a queen size bed, bedroom 2 has 2 twin beds, and Living room has a sofa that folds out into a twin size bed. Cable TVs and WiFi, and a beautiful lake view. We are located on the second floor so you will have steps to walk up. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach.

Beach Chic Condo 1 Block from Boardwalk
If a get-away is what you need, then simply "My Beach Hideout’ is what you want. Completely renovated 2 Bedroom/1 Bath condo a short one-block walk from the oceanfront. Enjoy a stylish, relaxed coastal-vibe experience. Perfectly comfortable for 4 guests or a solo long-business stay. Dining, nightlife, entertainment, events, VB boardwalk & shops all within walking distance. Immaculate condo has queen bed + TV in both bedrooms, living room, stocked kitchen, bath + parking.

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

Vibe District • Walk to Beach • Parking • Sleeps 6
Stay in the heart of Virginia Beach's Vibe Creative District—just a short walk to the beach and Boardwalk 🌊 Enjoy Atlantic Park, which is home to year-round surfing, along with The Dome concert venue and numerous new restaurants—all within two blocks. The Virginia Beach Sportsplex is also nearby. This 3-story condo offers a fully equipped kitchen, in-unit laundry, and a comfortable layout—perfect for families, small groups, or a fun coastal getaway.

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.
Popular amenities for Chesapeake condo rentals
Weekly condo rentals

Shadowlawn Villas II, Suite II, close to surf park

Life’s A Beach

Sunny Sands Getaway – Walk to the Beach

Clean, Calm, Contemporary home mins from Beach

Spacious Captain’s Beach Suite Near Rudee Inlet

Good Vibes at the Beach

Oceanfront Gem VaB Studio Exceptional Views

Beach Bliss Oasis • Walk to Ocean & Boardwalk
Pet-friendly condo rentals

Pet-Friendly Condo Steps to Beach

Bay Breeze At Ocean View Beach Home

Entire apartment in Chesapeake, Virginia

Hampton Condo Near Buckroe Beach | Dogs OK

Ocean Bliss: Cozy Apt Retreat(D)

* Modern Victorian 2 bdr, 1 bath, eat in kitchen

*Mid/Long Term Rental* Cozy Home at Mary Roberts

Ocean Escape
Condo rentals with a pool

Beach Luxury Beachfront

Sandbridge Beach - DeepSeaSide Retreat

Oceanfront Condo with Spectacular Beach View

Paradise at the Beach

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Dolphin Beach condo-amazing view and indoor pool

Oceanfront Condo with Balcony & Pool

Oceanfront 3BR condo with balcony and pool
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $179 NZD | $193 NZD | $193 NZD | $186 NZD | $182 NZD | $177 NZD | $175 NZD | $179 NZD | $189 NZD | $179 NZD | $187 NZD | $181 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 |
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- Condo rentals Virginia
- Condo rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Regent University
- First Landing Beach
- Chrysler Museum of Art
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Currituck Club
- Currituck Beach Lighthouse
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- The Mariners' Museum
- Nauticus
- Town Point Park





