
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 €26 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.

Close 2 East Beach, EOV, King Bed, Top Floor C
Come relax and unwind at Max’s at 14th bay Apartment! Located only TWO blocks from the beach in the quiet East Oceanview neighborhood of Norfolk! It is the ideal getaway for families and the modern traveler. The apartment is on the third (TOP) floor and each bedroom is outfitted with a comfy memory foam mattress (1 king and 1 queen), work desk, and smart TV. In addition, there is high speed internet, washer and dryer. It is conveniently located minutes from restaurants, grocery stores, and brew
LocationValueCheck-in
4.88 out of 5 average rating, 142 reviews
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!
FamilyValueBathroom
4.86 out of 5 average rating, 169 reviews
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.
LocationValueAmenities
4.92 out of 5 average rating, 389 reviews
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!
FamilyLocationWifi
4.85 out of 5 average rating, 157 reviews
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.
LocationValueGrill
4.98 out of 5 average rating, 193 reviews
Comfy 3 Bedroom Hideaway Minutes From H.U. & Beach
Welcome To Our Place! Ideal For Family Trips, Traveling For Business, Staycations Or Baecations In The Downtown Hampton Area. The Home (Unit A) Is Equipped With Complimentary WiFi, 65” Smart TV, Fully Stocked Kitchen, Coffee Bar, Washer & Dryer! Walking Distance To Restaurants & Nightlife! 5 Min: Buckroe Beach Fort Monroe Hampton University 15 Min: Norfolk International Airport Norfolk Premium Outlets 25 Min: Busch Gardens Williamsburg Water Country USA Virginia Beach Oceanfront
LocationValueWalkability
4.9 out of 5 average rating, 131 reviews
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.
LocationValueCheckout
4.97 out of 5 average rating, 324 reviews
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!
FamilyLocationDecor
4.94 out of 5 average rating, 137 reviews
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.
ValueLocationHospitality
4.98 out of 5 average rating, 126 reviews
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.
LocationFamilyBathroom
4.83 out of 5 average rating, 105 reviews
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
ValueFamilyDecor
4.83 out of 5 average rating, 113 reviews
"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
FamilyLocationCondition
4.91 out of 5 average rating, 115 reviewsPopular amenities for Chesapeake apartment rentals
Weekly apartment rentals

Cozy first floor, two bedroom, one bath apartment.
FamilyLocationWalkability
4.76 out of 5 average rating, 29 reviews
The Southern Magnolia | 2br/1bth Home
LocationSleep qualityWifi
4.83 out of 5 average rating, 12 reviews
Private Boutique Apt •W/D• Near Casino & Downtown
LocationValueIndoor spaces
4.9 out of 5 average rating, 30 reviews
The Lodge! 1BR Studio with private entrance.
ValueLocationSleep quality
4.91 out of 5 average rating, 95 reviews
The Lighthouse-2 blocks to beach
LocationCheckoutOutdoor spaces
4.94 out of 5 average rating, 49 reviews
Cozy Getaway near Downtown & Naval Base
LocationNearbyParking
4.81 out of 5 average rating, 47 reviews
Playa Sin Olas
ValueFamilyComfort
4.92 out of 5 average rating, 39 reviews
Top Gun R&R I: 2+ Bedrooms & 2 Full Bathrooms
ValueLocationIndoor spaces
4.89 out of 5 average rating, 36 reviewsPrivate apartment rentals

Home away from home( 3 Bed)
LocationValueBack garden
4.91 out of 5 average rating, 160 reviews
1 BR Apartment near VA Beach
LocationValueAccuracy
4.94 out of 5 average rating, 31 reviews
North End Oceanfront 2BR • Balcony + Pool
FamilyLocationNearby
4.96 out of 5 average rating, 23 reviews
Relax & Enjoy 2 blocks to beach w/ pool
FamilyValueLong stay
4.95 out of 5 average rating, 56 reviews
* Penthouse on Atlantic Ave* 2bdrm
FamilyValueLaundry
4.66 out of 5 average rating, 173 reviews
Oct Discount Special! 2BDRM Beach Escape!
FamilyLocationAccuracy
4.92 out of 5 average rating, 25 reviews
Virginia Beach, Getaway
ValueFamilyAmenities
4.93 out of 5 average rating, 69 reviews
Private studio
LocationValueAccess
4.95 out of 5 average rating, 87 reviewsApartment rentals with a hot tub

Sunset Retreat
LocationValueBiking
4.98 out of 5 average rating, 53 reviews
616.A Coastal 1BR Beachside Stay w/ Hot Tub & Yard
LocationFamilyTV
4.71 out of 5 average rating, 154 reviews
Works 4 Me: New listing
LocationOutdoor spacesNearby
4.93 out of 5 average rating, 28 reviews
VA Beach Ocean Sands 1BR/1BA
FamilyLocationWalkability
5.0 out of 5 average rating, 5 reviews
Barclay Towers Ocean Front 1, Virginia Beach
FamilyLocationHospitality
4.64 out of 5 average rating, 14 reviews
Huge Oceanfront Penthouse 3Bed/3Bath 18th Floor

Virginia Beach Partial Ocean View
LocationFamilyPool

1BD Oceanfront Va Beach Sleeps 6
New place to stayWhen is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €84 | €84 | €84 | €84 | €97 | €102 | €105 | €108 | €89 | €92 | €93 | €93 |
| 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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- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with lake access Chesapeake
- Rentals with beach access Chesapeake
- Beach house rentals Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with pools Chesapeake
- Cottage rentals Chesapeake
- Family-friendly rentals Chesapeake
- Apartment rentals Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a hot tub Chesapeake
- House rentals Chesapeake
- Rentals with breakfast Chesapeake
- Guest house rentals Chesapeake
- Townhouse rentals Chesapeake
- Beachfront rentals Chesapeake
- Waterfront rentals Chesapeake
- Flat rentals Virginia
- Flat rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Buckroe Beach
- Carova Beach
- Cape Charles Beachfront
- 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
- Colonial Williamsburg's Merchants Square
- Currituck Beach Lighthouse
- The Military Aviation Museum
- The Mariners' Museum
- Back Bay National Wildlife Refuge-N
- Town Point Park
- Nauticus
- Hampton University
- Chrysler Museum of Art





