
Apartment holiday rentals in 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 $64 SGD 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
Top-rated apartment rentals in Chesapeake
Guests agree: these apartments 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.

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 & towels provided in season. Please note: due to the open layout of the building, there is no elevator.

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.

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.

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!

Walk to beach BEAUTIFUL 2BR 1BA condo
1 block to Ocean/Boardwalk on 9th and Pacific in the heart of resort town. Beautifully furnished, 600sq ft beach-themed condo. Beds sleep 4 (1 Q, 2 Twin) and comfortable sleeper sofa adds 2 more. Also close to Convention Center, Vibe District, new Sports Complex. Perfect for family w/children or 4 adults. Free parking for 1 vehicle in front of unit. Park your car and walk to so many restaurants, putt putt and shopping! Spend a min 2 nights Sept-May and stay longer early June to Labor Day!

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.

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..

Beach Condo Block Off Oceanfront!
Come enjoy everything Virginia Beach has to offer. Our condo has all of the comforts of home perfect for families. Bedroom has a king size bed and living room has sofa that pulls out into a full size sofa bed. TVs in both rooms. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do and you can walk to the beach in 3 minutes or less! 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.
Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals

Comfy 1BR w pond view Kingsmill

Cozy 1 Bd condo, 1 block from the beach!

Oceanfront Penthouse

Good Vibes at the Beach

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Oceanfront Condo with Balcony & Pool

Beach Chic Condo 1 Block from Boardwalk

Oceanfront Condo/ Pool/ Surfing/ Fishing / EW 1002
Pet-friendly apartment rentals

Bay Breeze At Ocean View Beach Home

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

Beachfront Getaway, Pet Friendly, Mermaid Suite

August Suite | Beach | Balcony | Fire Pit

Ocean Bliss: Cozy Apt Retreat(D)

Sea Life | Walk to Beach & Heated Pool, Dogs OK!

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

NEW! Prime Location @Beach Club -Tranquil Seascape
Apartment rentals with a pool

Beach Luxury Beachfront

Oceanfront Penthouse | 4BR Sunrise & Sunset Views

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

Paradise at the Beach

Dolphin Beach condo-amazing view and indoor pool

Boardwalk Oceanfront Studio near Top Dining

OceanKeyResort 2BR2BA Sleeps 6 Superior & Aquarium

Sun & Fun! Ocean/Bay views /3 pools, gym, arcade
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $132 SGD | $142 SGD | $142 SGD | $137 SGD | $135 SGD | $131 SGD | $130 SGD | $132 SGD | $140 SGD | $132 SGD | $138 SGD | $133 SGD |
| 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 |
Destinations to explore
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- Rentals with lake access Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a kayak Chesapeake
- Waterfront rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a firepit Chesapeake
- Beachfront rentals Chesapeake
- Rentals with pools Chesapeake
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- Rentals with breakfast Chesapeake
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- Rentals with beach access Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Smoking-friendly rentals Chesapeake
- Apartment rentals Virginia
- Apartment rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Old Dominion University
- Regent University
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- Neptune's Park
- First Landing Beach
- Currituck Club
- Currituck Beach Lighthouse
- The Military Aviation Museum
- The Mariners' Museum
- Nauticus
- Back Bay National Wildlife Refuge-N





