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

Total holiday rentals
Explore 40 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 1,110 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 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.

Tropical 2BR Condo Getaway 1 Block from the Beach!
Unwind at this gorgeous fully renovated getaway for your family and friends! This two bedroom, one bath beach home is one block from the ocean. This unit accommodates up to 4 adults. Each room is equipped with a smart TV and internet is provided. Our kitchen provides refrigerator, microwave, oven, dishwasher, toaster, Keurig, dishes, cutlery, bowls, pots and pans, and much more! Steps away from shopping and restaurants! This highly sought after vacation spot really is a home away from home.
ValueLocationIndoor spaces

Good Vibes at the Beach
Boutique style building with a pool, designated parking, and coded door access. 2 bedrooms and 2 baths with a full kitchen and all amenities. Enjoy the pool during the summer months (May28th-Sept. 30th) or walk another block to enjoy the Beach at all times of the year. Multiple restaurants of all types surrounding this location and a large Harris Teeter grocery store only steps away. Come enjoy the Beach Life where music and arts are abundant. Primary booking guest must be at least 21 yrs old
FamilyValueWifi

Oceanfront Loft: Free Parking & 1 Block from Beach
Welcome to your stylish coastal retreat at the Virginia Beach Oceanfront, a thoughtfully designed 285 sq. ft. one-bedroom apartment just steps from the beach, boardwalk, dining, entertainment, and everything that makes Virginia Beach one of the East Coast’s favorite vacation destinations. This bright and modern condo combines comfort, convenience, and an unbeatable location in the heart of Virginia Beach Oceanfront. "Guest Favorite" for those looking for an easy, relaxing VA Beach getaway.
ValueFamilyView

2 Bedroom Condo One Block from the Oceanfront!
Our newly renovated 2 bedroom condo ONE block from the boardwalk accommodates 6 people and is also perfect for families. Each bedroom has a flat screen TV; one with a queen bed and the other with a king bed. There is also a pull out sofa bed in the living room along with a large TV. This is a 2nd floor unit with one designated parking spot. Plenty to do for the whole family with the beach, boardwalk, shopping, restaurants, amusement parks, and many more activities all within walking distance.
FamilyLocationIndoor spaces

3bd Sandbridge - Sunset Bay views! Newly Remodeled
Welcome to "Heels in the Sand", a 3bed-2bath luxury condo in the exclusive Sanctuary at False Cape, the only oceanfront complex at Sandbridge in Virginia Beach. Inside, there is space aplenty with a open-concept living area with Roku TV, a fully-stocked gourmet kitchen, high-end finishes & sleeping for 9! Two huge patios offer stunning views of the scenic Back Bay. Free access to all condo amenities, including free parking, 3 pools, grills, and a fitness center! Your beach vacation awaits!
ValueLocationParking

VB Boardwalk Getaway (2b2ba) - Long or short term!
Located a block and a half from the lively Virginia Beach boardwalk, our condo is in the perfect spot for an East Coast beach getaway! I love catching the sunrise over the ocean and following it up with a trip to Parlor Doughnuts, right around the corner. There is a keypad at the main entrance of the building as well as one for our individual unit, so you won't need a key. The pool can be enjoyed between Memorial Day and Labor Day. We've lived here for a year - ask me for any recommendations!
LocationValueView

2 bedroom condo with oceanfront one block away!
Come enjoy everything Virginia Beach has to offer. Our cozy condo has all of the comforts of home and is perfect for families and accommodates 6 adults. Bedroom 1 has a king size bed w/TV, bedroom 2 has a queen size bed w/TV and the living room has a sofa that pulls out into a full size sofa bed w/TV. The Boardwalk, Shopping, Restaurants, and many more activities are all within walking distance. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach!
LocationFamilyBathroom

Beach Bliss Oasis • Walk to Ocean & Boardwalk
Stylish beach retreat just blocks from the ocean & boardwalk 🌊 Walk to the Virginia Beach Convention Center (3 blocks), top restaurants, and local attractions. Perfectly located for a relaxing getaway with everything you need just steps away. Please note: This is a multi-level home with multiple flights of stairs inside the property. Guests will need to use stairs to access different areas of the home, including the bedrooms. This may not be ideal for guests with mobility concerns.
FamilyLocationBiking

Beach Chic Condo 1 Block from Boardwalk
If a get-away is what you need, then simply "My Beach Hideout’ is what you want. Completely renovated 2 Bedroom/1 Bath condo a short one-block walk from the oceanfront. Enjoy a stylish, relaxed coastal-vibe experience. Perfectly comfortable for 4 guests or a solo long-business stay. Dining, nightlife, entertainment, events, VB boardwalk & shops all within walking distance. Immaculate condo has queen bed + TV in both bedrooms, living room, stocked kitchen, bath + parking.
LocationFamilyNearby

Cozy 1 Bd condo, 1 block from the beach!
Your family will be close to everything when you stay at this centrally-located, cozy condo. 1 bedroom, 1 bath just a block off the beach. Queen bed in master and pull out couch and futon in living room. (comfortably sleeps 4, could sleep up to 6) Cute, fully equipped kitchen and dining area for 2. Walking distance to the popular board walk and beach, restaurants, bars, shopping and nearby activities and attractions. Perfect for a couples get away or a small family stay!
ValueFamilySleep quality

Ocean Escape
Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Community pool area, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.
FamilyValueCondition

2 Bedroom Beach Condo Block Off Boardwalk
Come enjoy everything Virginia Beach has to offer. Our newly renovated condo has all of the comforts of home perfect for families. Bedroom 1 has a king size bed, bedroom 2 has a queen size bed, and Living room has sofa that pulls out into a full size sofa bed. TVs in all rooms. The Boardwalk, Shopping, Restaurants, and many more activities are all within walking distance. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach.
FamilyValueSleep quality
Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals

Paradise at the Beach
LocationValueTV

Spacious Captain’s Beach Suite Near Rudee Inlet
ValueLocationAccess

Oceanfront Penthouse
FamilyValueNearby

Oceanfront, beach, boardwalk, fun, dolphin, sunris
LocationValueOutdoor spaces

Condo living just steps from the sand
ValueLocationComfort

Oceanfront Penthouse | 4BR Sunrise & Sunset Views
FamilyLocationKitchen

Modern Condo in Virginia Beach, Virginia
LocationValueQuiet

Beachfront Condo/ Pool/ Surfing/ Fishing / EW 1202
LocationFamilyWalkability
Pet-friendly apartment rentals

*Mid/Long Term Rental* Cozy Home at Mary Roberts
LocationValueAir conditioning

Hampton Condo Near Buckroe Beach | Dogs OK
FamilyValueKitchen

August Suite | Beach | Balcony | Fire Pit
LocationFamilyCheck-in

Bay Breeze At Ocean View Beach Home
FamilyLocationSolo travel

Ocean Bliss: Cozy Apt Retreat(D)
LocationFamilyHospitality

Trendy 2024 Seaside Retreat
ValueLocationCheck-in

* Modern Victorian 2 bdr, 1 bath, eat in kitchen
FamilyLocationParking

Entire apartment in Chesapeake, Virginia
ValueLocationParks
Apartment rentals with a pool

New Renovated-Beach & Boardwalk at Your Door &Pool
LocationFamilyShared spaces

Oceanfront Gem VaB Studio Exceptional Views
FamilyValueCondition

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen
LocationFamilyComfort

Oceanfront Condo with Spectacular Beach View
LocationFamilyNearby

Beach Luxury Beachfront
LocationValuePool

Seas The Day of Virginia Beach
FamilyLocationHospitality

Spacious 2BR/2BA Condo | 1.5 Blocks to Oceanfront
ValueLocationIndoor spaces

Boardwalk Oceanfront Studio near Top Dining
FamilyLocationCondition
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $131 SGD | $141 SGD | $141 SGD | $155 SGD | $155 SGD | $157 SGD | $129 SGD | $131 SGD | $139 SGD | $131 SGD | $138 SGD | $132 SGD |
| 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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- Apartment rentals Virginia
- Apartment 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 Mariners' Museum
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- Town Point Park
- Nauticus
- Chrysler Museum of Art
- Hampton University





