Apartment holiday rentals in Chesapeake

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Top-rated apartment rentals in Chesapeake

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Top guest favourite
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.
Apartment in Virginia Beach
4.99 out of 5 average rating, 144 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 favourite
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.
Apartment in Virginia Beach
4.87 out of 5 average rating, 109 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

Top guest favourite
The living room showcases two spacious leather sofas facing a flat-screen television. Natural light floods the room through two large windows, adorned with light-colored blinds. A coffee table centers the space, complemented by decorative plants and artwork on the wall.
Apartment in Virginia Beach
4.95 out of 5 average rating, 132 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 favourite
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.
Apartment in Virginia Beach
4.9 out of 5 average rating, 253 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.

Top guest favourite
Apartment in Sandbridge
4.93 out of 5 average rating, 149 reviews

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!

Top guest favourite
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.
Apartment in Virginia Beach
4.92 out of 5 average rating, 371 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!

Top guest favourite
The outdoor pool area features a well-maintained pool surrounded by lounge chairs. A clear blue sky is noted above, with clouds adding texture. Nearby greenery and structures contribute to the atmosphere, allowing for a relaxing outdoor experience.
Apartment in Virginia Beach
4.98 out of 5 average rating, 106 reviews

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.

Top guest favourite
The living area features a light grey sofa, two teal armchairs, and a wooden coffee table. A woven basket holds a soft throw. In the background, a kitchenette is visible, along with cabinets and appliances, illuminated by natural light from skylights.
Apartment in Williamsburg
4.96 out of 5 average rating, 128 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 favourite
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.
Apartment in Virginia Beach
4.87 out of 5 average rating, 103 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 favourite
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.
Apartment in Virginia Beach
4.9 out of 5 average rating, 313 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 favourite
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.
Apartment in Virginia Beach
4.97 out of 5 average rating, 172 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

Top guest favourite
A workspace with a wooden desk and a comfortable chair is situated by large windows, offering expansive views of the ocean. Natural light streams in, highlighting the tranquility of the beach outside. The windows are framed by light-colored blinds, with a small plant placed on the desk.
Apartment in Willoughby
4.99 out of 5 average rating, 100 reviews

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 apartment rentals

When is the best time to visit Chesapeake?

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Quick stats about apartment rentals in Chesapeake

  • Total holiday rentals

    Explore 40 holiday rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake holiday rentals start at £37 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Chesapeake holiday rentals include wifi 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

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