Compare cheap apartments in Chesapeake, VA from 100+ providers!

790 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Chesapeake, VA apartments
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

790 Apartments or condos in Chesapeake, VA

Find Apartments in Downtown of Chesapeake, VA

Renting a downtown vacation apartment in Chesapeake, VA places you steps from local dining, historic neighborhoods, and bustling city nightlife.

Entire Apartment In Chesapeake, Virginia - Chesapeake, VA
9.8 11 reviews

Entire Apartment In Chesapeake, Virginia

apartment, Chesapeake
This Chesapeake condo offers prime access, located 2 minutes from I64 and minutes from the Oceanfront, Downtown Norfolk, and Busch Gardens.
This spacious 4-guest apartment features 2 bathrooms, a full kitchen, a private balcony, and a swimming pool, with optional weekly cleaning for longer stays.
Simply Amazing In Chesapeake - Chesapeake, VA
10 40 reviews

Simply Amazing In Chesapeake

apartment, Chesapeake
This Chesapeake home is conveniently located near shopping, dining, and entertainment options, just a short drive from Virginia Beach and Norfolk. The property has received excellent ratings for cleanliness, location, and overall experience.
This 3-bedroom, 2-bathroom home comfortably sleeps 8 guests. You'll enjoy modern appliances, a fully equipped kitchen, a private garden, and easy access to nearby attractions like the Ocean View boardwalk, Virginia Beach, and Rivers Casino.
The Full House - Chesapeake, VA
10 3 reviews

The Full House

apartment, Chesapeake
This Chesapeake vacation rental is conveniently located 2.6 miles from Portlock Galleries at SoNo and within 6 miles of Oak Grove Lake Park, Riverwalk Parkway Park and Playground, the Chesapeake Conference Center, and Chesapeake Regional Medical Center.
This three-bedroom, two-bathroom house sleeps five guests and offers amenities including Wi-Fi, air conditioning, a washer, a hair dryer, and a smoke-free environment.
The Full House - Chesapeake, VA
9.6 80 reviews

The Full House

apartment, Chesapeake
This Chesapeake apartment is located in a quiet neighborhood, just 20 minutes from the Virginia Beach oceanfront, offering easy access to the beach, boardwalk, and other attractions. The apartment has consistently received excellent ratings for user experience, location, and cleanliness.
This 3-bedroom, 2-bathroom home comfortably accommodates up to 6 guests. The apartment offers a full kitchen with a fridge, freezer, microwave, and dishwasher, as well as air conditioning, parking, and internet access.

Best Chesapeake, VA apartment rentals with air conditioning

Nyakio Suite - Chesapeake, VA
No reviews

Nyakio Suite

apartment, Chesapeake
Nyakio Suite is a 2-bedroom, 2-bathroom condo in Chesapeake, located 11 miles from Topgolf Virginia Beach and 13 miles from Norfolk Botanical Garden.
This 1100 sq ft condo accommodates up to 7 guests and features a private swimming pool, a fully equipped kitchen with a dishwasher, and complimentary Wi-Fi.
Waterfront Home Near Va Beach | Sleeps 16+ | 5br - Chesapeake, VA
10 2 reviews

Waterfront Home Near Va Beach | Sleeps 16+ | 5br

apartment, Norfolk
This waterfront condo in Coastal Virginia offers scenic views and is located less than 1 mile from Virginia Beach and near Naval Station Norfolk.
This 5-bedroom, 2-bathroom house sleeps 16 guests and features a kitchen with a fridge, air conditioning, garden, and parking, with outdoor café lights for evening enjoyment.
Sojourn At Colley Manor Unit 4 - Chesapeake, VA
10 1 review

Sojourn At Colley Manor Unit 4

apartment, Norfolk
This Ghent, Norfolk condo is centrally located near Colley Avenue's restaurants, major hospitals (CHKD, EVMS, Norfolk General), and offers easy access to downtown Norfolk via public transportation and to Virginia Beach and Ocean View.
This 1000-square-foot, two-bedroom, one-bathroom rental sleeps four, includes a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, parking, and contactless self check-in; a pack 'n play and high chair are available for rent.
Modern 2 Bdrm Home W/firepit, Game Console, Bikes - Chesapeake, VA
9.6 71 reviews

Modern 2 Bdrm Home W/firepit, Game Console, Bikes

apartment, Portsmouth
This Portsmouth vacation rental boasts convenient access to the 41-mile Seaboard Coastline Trail, perfect for exploring the Hampton Roads area.
The fully renovated house features two bedrooms, one bathroom, sleeps six (with an extra guest fee), includes a complete kitchen with dishwasher, a fenced backyard with a fire pit, and provides bikes for guests, all within a pet-friendly environment.

Frequently Asked Questions about apartment rentals in Chesapeake, VA

  • What are the top cultural and historical sites in Chesapeake, VA?

    The Chesapeake Bay Maritime Museum is a must-see for any history buff. It has a collection of historic ships and exhibits on the area's maritime history. The Great Bridge Battlefield and National Monument is another great place to learn about the area's past. It commemorates the Battle of Great Bridge, a key battle in the American Revolutionary War.
  • What are the best apartments in Chesapeake, VA?

  • What makes Chesapeake, VA unique or famous?

    Chesapeake is known for its beautiful waterfront, with miles of shoreline along the Chesapeake Bay and its tributaries. The city is also home to the Chesapeake Bay Bridge-Tunnel, a unique engineering marvel that connects the Virginia Peninsula to the Eastern Shore. And, of course, Chesapeake is famous for its delicious seafood, especially crabs and oysters.
  • What are the best apartments with a pool in Chesapeake, VA?

    Beautiful And Chic Studio Apartment, Cheshire Retreat and Artist's Retreat are the best apartments with a pool in Chesapeake, VA.

  • Where can you find the best local markets and street food in Chesapeake, VA?

    The Chesapeake Farmers Market is a great place to find fresh, local produce and other goods. It's held every Saturday from May to October at the Chesapeake City Park. The Chesapeake Food Truck Festival is another great option for trying local street food. It's held annually in the fall at the Chesapeake Conference Center.
  • What are the best apartments with a jacuzzi in Chesapeake, VA?

    The best apartments with a jacuzzi in Chesapeake, VA are Rock Star Mansion, Peace On The Lake and Gorgeous 1 Bedroom With Free Wifi & Street Parking.

  • How is the public transportation system in Chesapeake, VA?

    Chesapeake has a public bus system, Hampton Roads Transit, that operates throughout the city. It's a good option for getting around, but it's not as extensive as in some larger cities. If you're planning on exploring the surrounding areas, you'll likely need a car.
  • What are the best apartments for families and kids in Chesapeake, VA?

  • Which seasonal events or festivals should apartment renters look forward to in Chesapeake, VA?

    The Chesapeake Bay Wine Festival is a popular event held every fall. It features wine tastings, live music, and food vendors. The Chesapeake Bay Seafood Festival is another great event held every summer. It features live music, seafood vendors, and family-friendly activities.
  • What are the best pet friendly apartments in Chesapeake, VA?

  • What amenities are typically included in apartments in Chesapeake, VA?

    Most apartments in Chesapeake include basic amenities like central air conditioning, a refrigerator, a stove, and a dishwasher. Some apartments may also include a washer and dryer, a balcony, or a parking space.
  • What are the best apartments with parking in Chesapeake, VA?

Popular destinations

Discover Apartments with Balconies in Chesapeake, VA

A terrace with views of the city skyline is a fantastic reason to book a vacation apartment in Chesapeake, VA.

Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood. - Chesapeake, VA
No reviews

Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood.

apartment, Chesapeake
This Chesapeake apartment is located just a short distance from the Norfolk waterfront and a 20-minute drive from Virginia Beach, offering easy access to both urban amenities and coastal attractions. The surrounding area is peaceful and quiet, perfect for a relaxing getaway.
This one-bedroom, one-bathroom apartment can comfortably accommodate up to four guests. It features free curbside parking, a front porch for enjoying the outdoors, and amenities such as air conditioning, internet access, and a washer and dryer.
Lovely Town Home - Chesapeake, VA
9.6 68 reviews

Lovely Town Home

apartment, Virginia Beach
This 4-bedroom vacation home in Virginia Beach offers a tranquil retreat in a quiet residential area while being conveniently close to major attractions like Mount Trashmore Park, Virginia Beach Town Center, and Sandler Center for the Performing Arts, all within a 6-mile radius. It has received excellent user ratings.
The home features a spacious layout with a cozy fireplace, a fully equipped kitchen, and a comfortable sofa bed for additional sleeping arrangements. Guests can enjoy amenities such as a private spa tub, barbecue grills, and a lush garden, as well as free WiFi and a smoke-free environment. The home can accommodate up to 10 guests, making it an ideal choice for families or groups.
Spacious Modern 3-bedroom House In Beautiful Portsmouth City. - Chesapeake, VA
8.0 1 review

Spacious Modern 3-bedroom House In Beautiful Portsmouth City.

apartment, Portsmouth
This 4-bedroom, 3-bathroom apartment in Portsmouth is a 7-minute drive to Town Point Park and a 20-minute drive to Chesapeake Bay, with the Children's Museum of Virginia and Portsmouth Naval Shipyard Museum just 3 minutes away. This unit offers Wi-Fi, air conditioning, a smart TV, laundry facilities, a sunroom, and parking for up to 6 guests, with a check-out time of 11:00 AM.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews

Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8

apartment, Portsmouth
Located 0.9 miles from Rivers Casino Portsmouth, this house is ideal for travelers seeking a convenient location to explore the city's landmarks. With an excellent user rating, this 3-bedroom, 2-bathroom vacation home is perfect for groups of up to 6 people.
The house boasts a spacious 1000 square feet of floor area, a fully equipped kitchen, and a garden where guests can relax and unwind. Additional amenities include air conditioning, a terrace/balcony, parking, and free WiFi, ensuring a comfortable and enjoyable stay.

Search Family-Friendly Vacation Apartments in Chesapeake, VA

Choosing a vacation apartment built for families in Chesapeake, VA ensures city attractions are within easy reach, making for a stress-free stay.

Cambridge Knights A 3 Bedroom Home Full Of Charm - Chesapeake, VA
10 1 review

Cambridge Knights A 3 Bedroom Home Full Of Charm

apartment, Portsmouth
This Portsmouth vacation home is located near the beach, within a 3-mile radius of popular landmarks such as the Commodore Theatre and the Virginia Sports Hall of Fame and Museum. The house offers three bedrooms, two bathrooms, and can accommodate up to six guests.
Amenities include a fully equipped kitchen, multiple bathrooms, laundry facilities, free WiFi, a Smart TV, a smoke-free environment, parking, and a spa.
Condo ∙ 1 Bedroom ∙ 6 Guests - Chesapeake, VA
No reviews

Condo ∙ 1 Bedroom ∙ 6 Guests

apartment, Chesapeake
Located in Chesapeake, Virginia, within a 25-minute drive of the Virginia Beach oceanfront, this 1 Bedroom Suite offers a convenient and comfortable stay for travelers visiting Chesapeake. The apartment features a modern and comfortable interior design, with a fully-equipped kitchen and air-conditioned living space. It can accommodate up to 6 guests and has 1 bedroom and 1 bathroom.
The apartment includes amenities such as free Wi-Fi, cable television, a DVD player, a washer and dryer, and complimentary parking. Guests can also enjoy access to an indoor pool, hot tub, complimentary breakfast buffet, 24-hour business and fitness centers, and evening receptions with food and drinks.
Cozy Modern Cabin - Historic - Chesapeake, VA
9.4 179 reviews

Cozy Modern Cabin - Historic

apartment, Portsmouth
This brick cabin is located in Portsmouth, just a 10-minute drive from the downtown area, offering stunning views of the Elizabeth River. Guests rave about the excellent location, cleanliness, and overall experience.
This four-bedroom home features a fully equipped kitchen with modern appliances, a large TV with Roku, and a private backyard with seating. Enjoy the shade of the canopy trees, explore nearby walking trails, and take advantage of the free laundry soap provided.
The Birds Nest - Chesapeake, VA
9.8 64 reviews

The Birds Nest

apartment, Chesapeake
This Chesapeake apartment is located in the Great Bridge area, just 20 minutes from the oceanfront, 5 minutes from the interstate, and 6 miles from Greenbriar Mall, offering a peaceful country atmosphere despite being in the city. The apartment has consistently received excellent ratings for user experience, location, and cleanliness.
This spacious rental accommodates up to 8 guests, making it ideal for families or groups. Enjoy a variety of amenities, including a fenced yard, a gazebo with electricity, a treehouse, and a jacuzzi, along with a fully equipped kitchen and internet access.

Guest-Favorite Apartments with Parking in Chesapeake, VA

Park your car and enjoy the city center; each of these vacation apartments in Chesapeake, VA comes with a free on-site parking spot.

The Hive - Chesapeake, VA
9.3 14 reviews

The Hive

apartment, Norfolk
Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
No reviews

Cheerful 2 Bedroom Home Near Virginia Wesleyan

apartment, Virginia Beach
3br, 6 Beds  Prime Stay Near Rivers Casino! - Chesapeake, VA
10 2 reviews

3br, 6 Beds Prime Stay Near Rivers Casino!

apartment, Portsmouth
15 Minutes To The Beach Bungalow - Chesapeake, VA
9.2 62 reviews

15 Minutes To The Beach Bungalow

apartment, Norfolk

Compare Luxury Apartments in Chesapeake, VA

A city-center luxury vacation apartment in Chesapeake, VA sets a wonderful tone for your visit, offering 5-star comfort throughout.

The Norfolk Nomad: Spacious 4br | Luminest Homes - Chesapeake, VA
10 1 review

The Norfolk Nomad: Spacious 4br | Luminest Homes

apartment, Norfolk

Popular Pet-Friendly Apartments in Chesapeake, VA

These dog-friendly vacation apartments in Chesapeake, VA ensure your pet feels right at home while you explore the city.

Sojourn At Colley Manor Unit 6 - Chesapeake, VA
No reviews

Sojourn At Colley Manor Unit 6

apartment, Norfolk
The Cozy Dominion Suite In Chesapeake - Chesapeake, VA
8.4 87 reviews

The Cozy Dominion Suite In Chesapeake

apartment, Chesapeake
Colorul & Cute Perfect Family & Pet-friendly Stay! - Chesapeake, VA
10 5 reviews

Colorul & Cute Perfect Family & Pet-friendly Stay!

apartment, Portsmouth
Beautiful, Modern Furnished 3-bedroom, 2-bathroom Cottage Near Attractions. - Chesapeake, VA
10 13 reviews

Beautiful, Modern Furnished 3-bedroom, 2-bathroom Cottage Near Attractions.

apartment, Portsmouth

Top Vacation Apartments with Swimming Pool in Chesapeake, VA

On-site pool access in Chesapeake, VA makes a proper swim in the heart of the city a wonderful part of your daily routine.

Nyakio Suite - Chesapeake - Chesapeake, VA
No reviews

Nyakio Suite - Chesapeake

apartment, Chesapeake
Vb Palm View: Furnished Monthly Rental - Sleeps 12 - Chesapeake, VA
10 15 reviews

Vb Palm View: Furnished Monthly Rental - Sleeps 12

apartment, Virginia Beach
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great For Business Travelers! - Chesapeake, VA
No reviews

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great For Business Travelers!

apartment, Chesapeake
Whispering Woods Estate- Secluded And Spacious - Chesapeake, VA
9.9 33 reviews

Whispering Woods Estate- Secluded And Spacious

apartment, Virginia Beach

Traveler-Approved Vacation Apartments with Jacuzzi in Chesapeake, VA

Coming home to a hot tub after a day in Chesapeake, VA changes the whole feel of a stay; every vacation apartment here features one.

Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth - Chesapeake, VA
8.6 11 reviews

Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth

apartment, Portsmouth
The Mermaids Oasis - Chesapeake, VA
9.7 6 reviews

The Mermaids Oasis

apartment, Virginia Beach
The Chesapeake Gray  Historical Waterside District 20 Mins To Oceanfront - Chesapeake, VA
9.4 8 reviews

The Chesapeake Gray Historical Waterside District 20 Mins To Oceanfront

apartment, Norfolk
Spacious 4br-corporate/military & Medical Stay - Chesapeake, VA
No reviews

Spacious 4br-corporate/military & Medical Stay

apartment, Suffolk
©2026 cozycozy.com