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

Total holiday rentals
Explore 160 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $43 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
150 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 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.

Getaway Minutes from the Beach
Discover our 2-bedroom, 1-bathroom apartment at the heart of the city, steps from top dining, shops, and entertainment. Enjoy a well-equipped kitchen, comfy living space with a pull-out sofa, and a bathroom with amenities. Conveniently near Buckroe Beach, Boo Williams Sportsplex, Hampton Virginia Aquaplex, Williamsburg, and Busch Gardens, it's your ideal vacation spot. We're dedicated to ensuring your fantastic experience and offer assistance with recommendations. Welcome to your city escape!

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.

Home away from home( 3 Bed)
Beautiful home with three bedrooms and one bathroom. Just a short walk to the bay. Large front porch to enjoy your morning coffee. COVA coffee and brewery is nearby. Newly remodeled home, super clean. Large backyard to enjoy your vacation nights. Spend sunny summer days at Ocean View Beach or explore the sights and sounds of nearby First Landing State Park, followed by a quick bite to eat at a local seafood restaurant. You will truly feel like you're on vacation here…………………………

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

Best location in Olde Towne Portsmouth
This apartment is available for up to 6 months upon request. Perfect location for traveling medical professionals. Very convenient to the Naval Medical Center. Enjoy Historic Old Towne and stay in a home built in 1850. Stroll the neighborhood where you will see houses from the late 1700's. Take a short walk to numerous restaurants or take in a movie at the historic Commodore Theater. Two blocks away is the ferry terminal to Waterside in downtown Norfolk.
Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals

Top Gun R&R I: 2+ Bedrooms & 2 Full Bathrooms

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

The Southern Magnolia | 2br/1bth Home

Beautiful historic apartment

Quaint Quarters Oceana

Sojourn's Harborage

Cozy apartment close to a beach

Old world charm
Private apartment rentals

Virginia Beach, Getaway

Private Backyard Oasis - Walk2Beach and fun!

2BR Getaway in the Heart of Norfolk

Relax & Enjoy 2 blocks to beach w/ pool

2 king beds 2nd fl walk 2 Beach apt2

Centrally Located Sleek Studio Apartment

Beachwalk #5, 8 Mins to Beach!

Private studio
Apartment rentals with a hot tub

Virginia Beach 1 Bedroom Villa

Oceanfront resort & unit, indoor/outdoor pool, spa

FourSailsResort Double Balcony OceanfrontJettedTub

Beach Quarters Resort - The Continental Suite

Works 4 Me: New listing

Sunset Retreat

2 Bedroom Ocean front, Ocean Beach Club Resort

Oceanaire Studio
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $136 AUD | $136 AUD | $136 AUD | $141 AUD | $151 AUD | $157 AUD | $170 AUD | $176 AUD | $144 AUD | $150 AUD | $151 AUD | $151 AUD |
| 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 outdoor seating Chesapeake
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- Guesthouse rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a hot tub Chesapeake
- Family-friendly rentals Chesapeake
- Condo rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with lake access Chesapeake
- Beach house rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with breakfast Chesapeake
- Townhouse rentals Chesapeake
- Beachfront rentals Chesapeake
- Rentals with pools Chesapeake
- Cottage rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Waterfront rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- House rentals Chesapeake
- Fitness-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
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Regent University
- First Landing Beach
- Neptune's Park
- Chrysler Museum of Art
- Currituck Club
- Colonial Williamsburg's Merchants Square
- Currituck Beach Lighthouse
- The Military Aviation Museum
- The Mariners' Museum
- Back Bay National Wildlife Refuge-N
- Nauticus
- Town Point Park





