
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 $52 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.

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.

Private Boutique Apt •W/D• Near Casino & Downtown
Stylish private second-floor apartment in a charming 1915 historic home in Westhaven. 647 sq ft with a queen bedroom, twin daybed room, and a comfortable sofa suitable for one sleeper. Full bath with tub/shower. Living room and dinette for 4. Kitchenette with fridge, microwave, 2-burner cooktop, and coffee maker. In-unit washer/dryer and two TVs. Minutes to Rivers Casino, NNSY, hospitals, Naval Station Norfolk, Beach, and the airport. No pets. No smoking inside. Private entrance & easy parking.

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.

"The Ponderosa B" - Close to the Casino & Concerts
Check out the outdoor concerts at the Rivers Casino. Only 1/2 mi. Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, family oriented neighborhood. Kick back and relax in this calm, stylish space. Private entrance and nice, safe, free parking for 1 vehicle. Large Sign for each Visitor Parking Space. One Bedroom w/very comfortable 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.

The Lodge! 1BR Studio with private entrance.
Welcome to the Lodge! Centrally located 15 min away from downtown Virginia Beach and 20 min from the Boardwalk. This cozy studio sleeps up to 2 people with one bedroom, one bathroom, full size bed and kitchenette with cooktop. Fully stocked with clean linens, towels, cookware and essentials. Free parking is available in the front and side of the home. This special place is close to everything, making it easy to plan your visit. Feels welcoming from the moment you walk in the door.

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.
Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals

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

Beautiful historic apartment

Quaint Quarters Oceana

Modern Studio near Downtown and the Navy Base

Sojourn's Harborage

Cozy apartment close to a beach

Cozy duplex near Oceana Base: A

Old world charm
Private apartment rentals

Virginia Beach, Getaway

2BR Getaway in the Heart of Norfolk

City Bliss: Stylish 1BR Escape

North End Beach Cottage Apt - One Block from Beach

Relax & Enjoy 2 blocks to beach w/ pool

Private studio

Beautiful 1 bed duplex apartment

Playa Sin Olas
Apartment rentals with a hot tub

Virginia Beach 1 Bedroom Villa

Beach Quarters Resort - The Continental Suite

Oceanaire, a Hilton Vacation Club Studio

OceanKey 1BR1BA Balcony Unit &Extras ALL FEES INCL

Works 4 Me: New listing

Sunset Retreat

2 Bedroom Ocean front, Ocean Beach Club Resort

VA Beach Ocean Sands 1BR/1BA
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $164 NZD | $164 NZD | $164 NZD | $171 NZD | $183 NZD | $190 NZD | $206 NZD | $212 NZD | $174 NZD | $181 NZD | $183 NZD | $183 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
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Myrtle Beach Holiday rentals
- Charlotte Holiday rentals
- Ocean City Holiday rentals
- North Myrtle Beach Holiday rentals
- Virginia Beach Holiday rentals
- Raleigh Holiday rentals
- Wilmington Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Beachfront rentals Chesapeake
- Waterfront rentals Chesapeake
- Rentals with lake access Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with beach access Chesapeake
- Beach house rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with pools Chesapeake
- Rentals with a kayak Chesapeake
- Cottage rentals Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Condo rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a hot tub Chesapeake
- House rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with outdoor seating Chesapeake
- Guesthouse rentals Chesapeake
- Townhouse 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





