
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 $51 NZD 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.
ValueLocationCleanliness

Centrally Located Sleek Studio Apartment
Private guest studio apartment with separate parking/entrance in a quiet neighborhood. Centrally located to shopping, restaurants , and parks. Airport:12 min CNU:6 min Riverside Medical Center:7 min Sentara Hospital:8 min Langley AFB:11 min Patrick Henry Mall:8 min Willimasburg/Bush Gardens: approx 30 min Virgina Beach Oceanfront: 45 min Wifi available with a 55" TV with streaming services (no cable). Coffee table folds into dining/work table. Stools under table. Full bath/kitchen/laundry unit.
FamilyValueNearby

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!
FamilyValueLong stay

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!
FamilyLocationDecor

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.
FamilyLocationHot tub

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.
LocationValueBathroom

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.
FamilyValueCheck-in

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…………………………
FamilyLocationDecor

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!
FamilyLocationCondition

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.
ValueLocationTV

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.
LocationValueHospitality

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
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Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals

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

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

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

Beautiful historic apartment
ValueLocationParking

Quaint Quarters Oceana
ValueLocationAmenities

Cozy apartment close to a beach
ValueLocationParking

Old world charm
ValueFamilyNearby

Cottage 2 Blocks to Virginia Beach Oceanfront - I
FamilyValueTV
Private apartment rentals

Virginia Beach, Getaway
FamilyValueParking

2BR Getaway in the Heart of Norfolk
LocationValueBathroom

2 King Beds + 400ft from Beach U8
ValueLocationWalkability

Cozy Cute Apartment
ValueFamilySleep quality

Relax & Enjoy 2 blocks to beach w/ pool
FamilyValueLaundry

Private studio
FamilyLocationLaundry

Playa Sin Olas
ValueLocationNearby

Granny Chic Suite | Full Kitchen, W/D, King Bed
LocationFamilyOutdoor spaces
Apartment rentals with a hot tub

Virginia Beach 1 Bedroom Villa

Beach Quarters Resort - The Continental Suite
FamilyLocationHospitality

Oceanaire, a Hilton Vacation Club Studio

Works 4 Me: New listing
LocationOutdoor spacesBiking

Sunset Retreat
LocationValueAccuracy

2 Bedroom Ocean front, Ocean Beach Club Resort
LocationFamilyBiking

VA Beach Ocean Sands 1BR/1BA
FamilyLocationBeach

Virginia Beach 2BR Condo With Pool Access
LocationFamilyWalkability
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $162 NZD | $162 NZD | $162 NZD | $162 NZD | $187 NZD | $198 NZD | $203 NZD | $210 NZD | $172 NZD | $179 NZD | $181 NZD | $181 NZD |
| 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 a kayak Chesapeake
- Rentals with pools Chesapeake
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- Rentals with a hot tub Chesapeake
- House rentals Chesapeake
- Rentals with breakfast Chesapeake
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- Waterfront rentals Chesapeake
- Apartment rentals Virginia
- Apartment rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Regent University
- First Landing Beach
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Currituck Beach Lighthouse
- The Mariners' Museum
- Chrysler Museum of Art
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- Town Point Park
- Nauticus
- Virginia Living History Museum
- Currituck Beach





