
Apartment vacation 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.

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.

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.

English Basement Hide-Away
Private Suite in the heart of Olde Towne, Portsmouth! This historic English Basement style home has a private street entrance. Walking distance from the the waterfront, restaurants, local shopping, Coast Guard Base and Navy Hospital, Atlantic Union Bank Pavillion, ferry into Downtown Norfolk, The Norva, and the Tides Stadium. 9 minute drive to the Rivers Casino. Quick drive to Military Bases, and approx. a 20 minute drive to VA Beach and a 45 minute drive to Williamsburg/Busch Gardens.

The Nook
Enjoy a getaway in this cozy 1 bedroom apartment attached to a classic 1940s Cape Cod home minutes from Colonial Williamsburg and Jamestown. You'll be within biking distance to many local attractions such as Williamsburg Winery, Jamestown Island, Jamestown Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The Nook was completely refinished in 2020. Need more space or traveling with a group? Inquire about our other units.

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!

Fully Renovated Beach Loft Block Off OceanFront
Come enjoy everything Virginia Beach has to offer. Our newly renovated beach condo has all of the comforts of home and accommodates 2-3 adults perfectly. Bedroom has a queen size bed and common area has a futon that pulls out into a bed. Smart TVs in both rooms. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. You can walk to the beach in 3 minutes or less! Come have a relaxing and fun vacation at the beach.

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony
Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee on the balcony while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

Elegant Cozy Colonial/Private/Self Check-in
This beautiful 3800 Sq ft Colonial home was built in 1880..previously known as Sycamore Farm, and was featured in Elle Magazines 2000 Christmas edition. The Guest portion of the home is an attached carriage house. The first floor features a large 1134 Sq ft living space that is dedicated entirely to guests. Above it is a locked unoccupied attic. The house is very private and secluded, and is surrounded by bamboo. Private driveway, with space for one vehicle.

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

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

LiveEOV: Beachcomber Two

Cozy apartment close to a beach

Beautiful 1 bed duplex apartment

Cozy duplex near Oceana Base: A

In the Heart of Norfolk

Efficiency in Historic Elizabeth City
Private apartment rentals

Spacious apartment

North End Beach Cottage Apt - One Block from Beach

The Liberty Flat

Governor’s Green 1BR Dlx Condo w/ Full Kitchen

The SEA-renity 11

Cluff Pool Collection: Pool's Porch

Beach Luxury Oceanfront

VA Beach Ocean Sands 1BR/1BA
Apartment rentals with a hot tub

Direct Beachfront on Boardwalk facing Ocean

Kingsgate 1 BedrooM

Cozy studio suite near Williamsburg historic area.

Corolla Oceanside Hideaway, 5 min walk to beach

Kingsgate Resort 3 Bedroom Lockoff

Kingsgate Resort 2 Bedroom

Works 4 Me: New listing

Bayside condo on the beach in Sandbridge
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$20,070 GYD | G$19,861 GYD | G$20,279 GYD | G$20,697 GYD | G$22,161 GYD | G$22,997 GYD | G$24,042 GYD | G$23,624 GYD | G$21,952 GYD | G$20,906 GYD | G$20,906 GYD | G$20,906 GYD |
| 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 apartment rentals in Chesapeake

Total vacation rentals
Explore 160 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at G$4,181 GYD per night before taxes and fees

Verified guest reviews
Over 6,280 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
150 of Chesapeake vacation rentals include wi-fi 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 Cinema Cafe-Greenbrier Mall
Destinations to explore
- New York Vacation rentals
- Washington Vacation rentals
- Myrtle Beach Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Charlotte Vacation rentals
- Outer Banks Vacation rentals
- Ocean City Vacation rentals
- Cape Fear River Vacation rentals
- Jersey City Vacation rentals
- Virginia Beach Vacation rentals
- Rentals with pools Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Waterfront rentals Chesapeake
- Cottage rentals Chesapeake
- Condo rentals Chesapeake
- Beach house rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with a kayak Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with beach access Chesapeake
- House rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Guesthouse rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Smoking-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with lake access Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a washer and dryer Chesapeake
- Rentals with breakfast Chesapeake
- Beachfront rentals Chesapeake
- Apartment rentals Virginia
- Apartment rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Outlook Beach
- Kiptopeke Beach
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Virginia Beach National Golf Club
- Chrysler Museum of Art
- Golden Horseshoe Golf Club
- Cape Charles Beachfront
- James River Country Club
- Wilkins Beach
- Little Creek Beach
- Red Wing Lake Golf Course