
Apartment holiday rentals in Chesapeake
Find and book unique apartments on Airbnb
Quick stats about flat rentals in Chesapeake

Total holiday rentals
Explore 160 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 6,430 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
150 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 Aerotheater
Top-rated apartment rentals in Chesapeake
Guests agree: these apartments are highly rated for location, cleanliness and more.

Private apartment only 3 blocks from the Beach
Newly remodeled, super clean one bedroom (in-law) apartment, approx. 375 sf. Three blocks from the beach 7-10 min walk. Covered deck, backyard on water to watch ducks, herons, fish. Concrete benches and firepit near the water. Walking distance to the ocean, boardwalk, Rudee Inlet, dining and entertainment. Hardwood floors, queen size bed, 'pack n play', kitchenette with sink, refrigerator, microwave, Keurig coffee maker, toaster (no oven or stove) 1 gig mbps Wifi, internet tv. Futon-like couch.

Near Beach Eclectic Retreat
Unwind in our urban oasis: a 2-bed, 1-bath apartment moments from dining, shops, and entertainment. Your comfort is paramount, with a fully equipped kitchen, cozy living space, and a pull-out sofa. With proximity to Virginia Beach, Portsmouth Casino, Buckroe Beach, Busch Gardens, Boo Williams Sportsplex, Virginia Beach Sportsplex and Hampton WaterPlex, your dream vacation is at your doorstep. Count on us for personalized suggestions to elevate your stay. Welcome to the ultimate city retreat!

5 Minute Walk to the Beach!
Large private first floor room with its own private entrance. 5 minute walk to the beach. Enjoy the beach, shops, dining, boardwalk & everything the Oceanfront has to offer! Easy access to interstate 264 makes traveling to and from a breeze. Queen memory foam bed with private full bathroom. Access to outside oasis including gas grill & 2 beach cruiser bikes to explore this fantastic beach town. Private room also includes a spacious living space with couch, mini fridge, freezer and microwave.

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Enjoy easy access to everything from this perfectly located, fully furnished home. Walk to fine dining, museums, a historic theater. Visit the waterfront where you can view the Navy ships or ride the Ferry to Norfolk to experience Waterside & MacArthur Mall. This is a great place for traveling professionals or those in town for sightseeing or local events. Virginia Beach Oceanfront is 30 minutes away. Home is located in a beautiful, historic area and only 8 minutes from the new casino!

Modern Luxury Peace & Quiet.
Covered parking with EV Charger. With one acre fenced in yard. 1000+ sq ft Modern Second Floor Guest House apartment with separate private entrance attached to a 10,000+ sq ft Mansion on 3 acres in a very safe, quiet and private neighborhood. Free private parking. Minutes from restaurants, shopping centers, and a beautiful 30 minute drive to oceanfront. Free Netflix, High Speed WiFi, washer, dryer, full kitchen. With Keurig. Brand new Heat and Air Condition! Plus 2 dedicated parking spots.

Charming cozy apt historic in Old Towne Portsmouth
Newly renovated, newly furnished, cozy and relaxing 1 bd 1 bath apt is available for your stay. Coffee shops, museums, restaurants, bars and the Commodore Theater are all within steps. The ferry to downtown Norfolk is a quick walk and most Saturday mornings the Farmers Market is literally around the corner. If you are in town for a concert, the Amphitheater is a short walk away. This is a 1st floor apartment in a duplex. The only coomon area is the main entrance to the building and foyer.

Cozy Ground Floor Apt in Historic Home
Charming 1st floor apartment with private entrance in circa 1795 home in the Olde Towne historic neighborhood. Guests enjoy an easy walk to downtown shops, restaurants, breweries, museums, and a movie theater. The waterfront is close with marinas, restaurants, and the Elizabeth River ferry to transport you to Norfolk to enjoy events on the waterfront. Business or military travelers are two blocks from the Renaissance Hotel and a 15-minute walk from the Portsmouth Naval Hospital.

Lovely Two Bedroom, 1 1/2 bath, King bed Townhouse
Your family will be close to everything when you stay at this centrally-located place. Beautiful re-done townhouse. New carpet and luxury vinyl, new vanities and toilets, Maytag washer and dryer, central heat and air, brand new hot water tank, small patio in back. Close to shopping, Kroger, T J Maxx, Walmart, CVS, and other shops. Plenty of take out food, like chick-fil-A, Panda Express, Wendys, Rallys, Dunkin Donuts, and more. Brand new Rivers Casino less than a mile away!

Blissful Nook @ Washington
This is a beautiful modern, comfortable, and cozy one bedroom apartment located on the second floor (stair access) above the car garage. While relaxing or vacationing just know that this apartment is centrally located to Virginia Beach Oceanfront, Outer banks N.C. museums, Colonial Williamsburg, Busch garden, Water Country USA and many restaurant. This apartment is attached to the main home with a dedicated private entrance. This location is safe and private for our guest.

The Rosalie Suite 4, Steps from Norfolks Hospitals
A secluded, furnished one-bedroom hotel-like apartment. A seamless self-check-in grants you access to an ideal living space. A home away from home, complete with a convenient kitchen, we provide all the essentials in the cabinets—fast firewall-protected 5g wifi with a space to work and more to relax. Arise to an instant hot shower and a quick Keurig brew, and secure your suite with a press of a button before heading into town. We trust you will enjoy our unmatched amenities.

Ocean Getaway
Just one block from the beach, this beautifully remodeled apartment is the perfect coastal retreat! Enjoy a stylish, comfortable space with everything you need for a relaxing getaway. Located near top-rated breweries, restaurants, and local favorites — you’ll be right in the heart of all the action. Please note: • This is an apartment unit — no parties allowed • Ring camera at front door for guest and property security • Maximum 1 parking space for Airbnb guests

"The Ponderosa A" - Close to the Casino & Concerts
Lots of Great Concerts going on Check out the outdoor concerts at the Rivers Casino. Only 1/2 mile away. 600 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, nice, quiet neighborhood 1/2 mile to the Private entrance and nice, free Private entrance parking for 1 vehicle. Large Sign Visitor Parking Space. One Bedroom w/Queen size bed, Full size Kitchen, One full Bathroom. Only 4 miles to Downtown Portsmouth , 5.9 miles to Norfolk, 22 mi to VB Oceanfront
Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals

Historic Gem Steps to the Beach w/Private Patio

1 BR Apartment near VA Beach

Serene Tree House Retreat | Spacious 1br/1bth Home

2 king beds 2nd fl walk 2 Beach apt2

The Lodge! 1BR Studio with private entrance.

Private Boutique Apt •W/D• Near Casino & Downtown

Cozy Getaway near Downtown & Naval Base

Playa Sin Olas
Private apartment rentals

Old world charm

Cozy Cute Apartment

Cozy apartment close to a beach

2BR Getaway in the Heart of Norfolk

The Lighthouse-2 blocks to beach

2BDRM Beach Escape! Relaxation, Sun and Fun!

Porch life in Sunbury

Historic private guest apartment
Apartment rentals with a hot tub

Sunset Retreat

616.B Coastal 1BR Stay w/ Hot Tub & Private Yard

Works 4 Me: New listing

Barclay Towers Ocean Front 2, Virginia Beach

VA Beach Ocean Sands 1BR/1BA

1BD Oceanfront Va Beach Sleeps 4

Oceanaire, a Hilton Vacation Club Studio

Virginia Beach Partial Ocean View
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $121 SGD | $121 SGD | $121 SGD | $121 SGD | $140 SGD | $147 SGD | $151 SGD | $156 SGD | $128 SGD | $133 SGD | $135 SGD | $135 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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- Flat rentals Virginia
- Flat rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Cape Charles Beachfront
- Buckroe Beach
- Carova Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Old Dominion University
- Norfolk Botanical Garden
- Regent University
- First Landing Beach
- Neptune's Park
- Currituck Club
- Currituck Beach Lighthouse
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- Town Point Park
- Chrysler Museum of Art
- Nauticus





