Condo vacation rentals in Chesapeake

Find and book unique condos on Airbnb

Quick stats about condo rentals in Chesapeake

  • Total vacation rentals

    Explore 40 vacation rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake vacation rentals start at G$10,456 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,070 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

  • 4.8 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.

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Top guest favorite
A modern living room features a gray sofa adorned with decorative pillows, paired with a light blue coffee table. Two lamps provide ambient lighting. Artwork of coastal scenes decorates the walls, while a patterned area rug enhances the room's coastal theme.
Condo in Virginia Beach
4.99 out of 5 average rating, 156 reviews

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.

Guest favorite
A clear view of a rectangular pool surrounded by a patio area. Lounge chairs are positioned near the pool, and a hot tub is visible adjacent to the water. Greenery and potted plants line the space, and a building with large windows is in the background.
Condo in Virginia Beach
4.87 out of 5 average rating, 111 reviews

Good Vibes at the Beach

Boutique style building with a pool, designated parking, and coded door access. 2 bedrooms and 2 baths with a full kitchen and all amenities. Enjoy the pool during the summer months (May28th-Sept. 30th) or walk another block to enjoy the Beach at all times of the year. Multiple restaurants of all types surrounding this location and a large Harris Teeter grocery store only steps away. Come enjoy the Beach Life where music and arts are abundant. Primary booking guest must be at least 21 yrs old

Guest favorite
A serene landscape captures a sunset over the James River, with vibrant hues of orange and pink reflecting on the water. Silhouettes of trees frame the view, and a gently sloping green lawn leads toward the riverbank, enhancing the tranquil atmosphere.
Condo in Williamsburg
4.94 out of 5 average rating, 145 reviews

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.

Top guest favorite
A living area features comfortable seating with plush couches and a woven coffee table. Large windows provide natural light, and a dining area with a blue fabric table set is visible. Decorative elements include a ceiling fan and wall art.
Condo in Virginia Beach
4.95 out of 5 average rating, 134 reviews

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.

Guest favorite
A spacious living area is shown, featuring a blue sectional sofa and a decorative rug in light tones. A flat-screen TV is mounted on the wall, and an adjacent dining area includes a white table with four chairs. Natural light filters through the windows.
Condo in Virginia Beach
4.9 out of 5 average rating, 265 reviews

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.

Guest favorite
A well-equipped kitchen and dining area are visible, with modern appliances and a stylish table set for six. A comfortable sofa in the living space is complemented by a soft area rug, enhancing the inviting layout. Natural light is allowed in by the open layout.
Condo in Virginia Beach
4.92 out of 5 average rating, 381 reviews

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!

Guest favorite
Condo in Virginia Beach
4.83 out of 5 average rating, 213 reviews

Beach Bliss Oasis • Walk to Ocean & Boardwalk

Stylish beach retreat just blocks from the ocean & boardwalk 🌊 Walk to the Virginia Beach Convention Center (3 blocks), top restaurants, and local attractions. Perfectly located for a relaxing getaway with everything you need just steps away. Please note: This is a multi-level home with multiple flights of stairs inside the property. Guests will need to use stairs to access different areas of the home, including the bedrooms. This may not be ideal for guests with mobility concerns.

Top guest favorite
Condo in Williamsburg
4.96 out of 5 average rating, 136 reviews

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..

Guest favorite
A comfortable living area is highlighted by a spacious sofa and a table with two high-backed chairs. Natural light enters through a window adorned with blinds. Wall art and a sign reading 'BEACH HOUSE' add a coastal touch to the space.
Condo in Virginia Beach
4.88 out of 5 average rating, 106 reviews

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!

Guest favorite
An open living area features a sectional sofa, a flat-screen TV mounted on the wall, and a small side chair. Light-colored cabinetry is seen in the kitchen area, accompanied by a dining table. Soft natural light brightens the space through large windows.
Condo in Virginia Beach
4.91 out of 5 average rating, 326 reviews

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.

Top guest favorite
A view of the beach stretches towards the horizon, framed by green grass and a flower pot. White lounge chairs are arranged for relaxation, while colorful umbrellas dot the sandy shore, providing shade to beachgoers enjoying the ocean.
Condo in Virginia Beach
4.97 out of 5 average rating, 183 reviews

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

Guest favorite
Condo in Virginia Beach
4.92 out of 5 average rating, 143 reviews

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.

Popular amenities for Chesapeake condo rentals

When is the best time to visit Chesapeake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,538 GYDG$23,211 GYDG$23,211 GYDG$22,375 GYDG$21,957 GYDG$21,329 GYDG$21,120 GYDG$21,538 GYDG$22,793 GYDG$21,538 GYDG$22,584 GYDG$21,748 GYD
Avg. temp6°C7°C10°C16°C20°C25°C27°C26°C23°C18°C12°C8°C

Destinations to explore

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