
Apartment holiday rentals in Chesapeake
Find and book unique apartments on Airbnb
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.

"The Ponderosa B" - Close to the Casino & Concerts
Lots of Great Concerts going on close by!! Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, family oriented neighborhood about 1/2 mile Rivers Casino! -, 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.

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.

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!

Walk to the Beach from Pretty Inn Pink
This 1920s home has retained its vintage charm while still featuring a contemporary decor. WALKING DISTANCE to beach, convention center and sportsplex. Guests have the entire upstairs unit. Sitting in the heart of the ViBe Arts District, the home is surrounded by dozens of beautiful murals. Walk the artful streets to delicious restaurants, charming cafes, and boutique shops before heading to the gorgeous beaches just a few blocks away. Great for traveling sports families!

Blissful Nook @ Washington
This is a beautiful modern, comfortable, and cozy one bedroom apartment located on the second floor 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.

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.

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 5 minute walk and every Saturday morning the Farmers Market is literally around the corner. If you are in town for a concert, the Amphitheater is a short walk away. Let us make your stay stress free and enjoyable.
Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals

Virginia Beach, Getaway

Comfy 3 Bedroom Hideaway Minutes From H.U. & Beach

Relax & Enjoy 2 blocks to beach w/ pool

2 king bed steps to beach Top Floor - 9

Quaint Quarters Oceana

Beachwalk #5, 8 Mins to Beach!

Private studio

Ocean Getaway
Private apartment rentals

New! Oceanfront Penthouse/ 2 Decks/ Pool/Beach/Gym

North End Beach Cottage Apt - One Block from Beach

Historic Charm & Modern Comfort : Downtown Escape

Tully's Lookout, a Quaint Oceanside Apartment

Sandbridge Beach Bay Getaway

Georgie's Brick Air BNB

Vibe District, Atlantic Surf Park, VB Sports Ctr

Portside Kid Friendly Fast Wi-Fi Self Check in
Apartment rentals with a hot tub

*No Resort Fees Powhatan 4 bdrm

FourSailsResort Double Balcony OceanfrontJettedTub

Great family accommodation. 4BDR Powhatan Resort

Williamsburg 3 Bedroom Suite!

Our Home Away from Home

Sleep 24! 8BDR/8BA Package. Multi-unit discount.

The Historic Powhatan Resort- 2 bdrm sleeps 6

Barclay Towers Ocean Front 1, Virginia Beach
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £72 | £71 | £73 | £74 | £79 | £82 | £89 | £92 | £76 | £79 | £79 | £79 |
| 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 |
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 £15 per night before taxes and fees

Verified guest reviews
Over 6,080 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
160 of Chesapeake holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake rentals

4.7 Average rating
Chesapeake stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chesapeake’s top spots include Chrysler Museum of Art, Nauticus and Cinemark Chesapeake Square
Destinations to explore
- New York City Holiday rentals
- Washington Holiday rentals
- Myrtle Beach Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Cape Fear River Holiday rentals
- Jersey City Holiday rentals
- Ocean City Holiday rentals
- Rappahannock River Holiday rentals
- Rentals with a fireplace Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Apartment rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Beach house rentals Chesapeake
- Cottage rentals Chesapeake
- Rentals with pools Chesapeake
- Waterfront rentals Chesapeake
- Rentals with lake access Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with beach access Chesapeake
- Townhouse rentals Chesapeake
- Guest house rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Beachfront rentals Chesapeake
- Rentals with a hot tub Chesapeake
- House rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with a firepit Chesapeake
- Flat rentals Virginia
- Flat rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Water Country USA
- Buckroe Beach
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Town Point Park
- Old Dominion University
- Hampton University
- Virginia Living History Museum
- First Landing Beach
- Chrysler Hall
- Currituck Beach Lighthouse
- Neptune's Park




