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Chesapeake, VA apartments
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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.

The Cozy Dominion Suite In Chesapeake - Chesapeake, VA
8.5 83 reviews

The Cozy Dominion Suite In Chesapeake

apartment, Chesapeake
This Chesapeake condo is conveniently located near shops and restaurants, with Downtown Norfolk a short 10-minute drive away.
The one-bedroom, one-bathroom apartment sleeps three, features a well-equipped kitchen with a dishwasher, and includes a smart TV, high-speed WiFi, and a Ring Doorbell for enhanced security.
Entire Apartment In Chesapeake, Virginia - Chesapeake, VA
9.8 8 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.
Fully Renovated And Modernized Home In Chesapeake - Chesapeake, VA
10 22 reviews

Fully Renovated And Modernized Home In Chesapeake

apartment, Chesapeake
This Chesapeake apartment is located close to Portlock Galleries at SoNo and Greenbrier Mall, offering easy access to art, shopping, and dining. It has received excellent user ratings, making it a popular choice for travelers. The 3-bedroom, 3-bathroom dwelling comfortably accommodates up to 8 guests. Enjoy modern amenities like a smart TV, Wi-Fi, a washer and dryer, a barbecue area, and a sofa bed for extra sleeping space.
Simply Amazing In Chesapeake - Chesapeake, VA
9.9 38 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.

Best Chesapeake, VA apartment rentals with air conditioning

Contemporary 5 Br, 4ba, Over 3500 Sf Water Front - Chesapeake, VA
10 5 reviews

Contemporary 5 Br, 4ba, Over 3500 Sf Water Front

apartment, Portsmouth
This waterfront house in Portsmouth's Churchland area offers direct Chesapeake Bay access and is a 15-minute drive to the River Casino, with nearby shopping and dining.
This 5-bedroom, 4-bathroom residence accommodates 14 guests and features a private boat dock, an expansive deck with a gas grill overlooking the Elizabeth River, an entertainment room with a pool and ping pong table, and complimentary Wi-Fi.
R & R River House - Chesapeake, VA
9.9 97 reviews

R & R River House

apartment, Portsmouth
This luxury condo in Portsmouth, Virginia is conveniently located approximately one mile from a city park and 4.5 miles from a casino, offering easy access to downtown Portsmouth (7 miles) and Virginia Beach (25 miles).
The two-bedroom, one-bathroom condo sleeps six guests and boasts a fully equipped kitchen with a fridge, microwave, and dishwasher, plus air conditioning, a garden, parking, and stunning water views from a private balcony.
Mid-century Modern Old Town Portsmouth 3bd/2.5 Bth - Chesapeake, VA
9.9 135 reviews

Mid-century Modern Old Town Portsmouth 3bd/2.5 Bth

apartment, Portsmouth
This charming Portsmouth home is located on a quiet street in Colonial Portsmouth, just blocks from the waterfront and a lovely park. The accommodation has earned excellent ratings for cleanliness, location, and overall guest experience.
The two-story home features a spacious living area, a dedicated playroom, and can accommodate up to 8 guests. The house is fully equipped with a kitchen, air conditioning, a garden, parking, and internet access.
Riverfront 3br Retreat  Near Rivers Casino - Chesapeake, VA
9.6 68 reviews

Riverfront 3br Retreat Near Rivers Casino

apartment, Portsmouth
This Portsmouth house rental boasts a peaceful waterfront location on the Elizabeth River, minutes from Historic Olde Towne Portsmouth and an 8-minute drive from Rivers Casino Portsmouth.
The three-bedroom, two-bathroom home sleeps six, features a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, high-speed WiFi, and ample parking.

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.

Historic Olde Towne 2 Bedroom 1 Bath 1100sq Ft Vacation Rental - Chesapeake, VA
9.0 53 reviews

Historic Olde Towne 2 Bedroom 1 Bath 1100sq Ft Vacation Rental

apartment, Portsmouth
This Portsmouth riverfront apartment is a short walk from the Commodore Theatre, Virginia Sports Hall of Fame, and Tidewater Yacht Marina, with the Children's Museum of Virginia and Portsmouth Naval Shipyard Museum within a 15-minute walk.
This two-bedroom, one-bathroom rental sleeps four, features free WiFi, on-site parking, a fully equipped kitchen including a dishwasher, and a terrace – perfect for exploring Portsmouth's attractions.
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.
A 4-br 2 Bath House In A Well Loved Neighborhood Centrally Located In Portsmouth - Chesapeake, VA
No reviews

A 4-br 2 Bath House In A Well Loved Neighborhood Centrally Located In Portsmouth

apartment, Portsmouth
This non-smoking vacation home in Portsmouth is located near entertainment venues, just a 12-minute drive from Norfolk Scope and Waterside District, and close to a water park and wildlife spotting opportunities.
This 2000 sq ft residence offers 4 bedrooms, 2 bathrooms, and accommodates up to 8 guests with amenities including a full kitchen, air conditioning, complimentary Wi-Fi, a private terrace, and on-site parking.
Historic Old Towne Southern Charm - Chesapeake, VA
9.4 40 reviews

Historic Old Towne Southern Charm

apartment, Portsmouth
This charming 18th-century home is situated in Old Towne Portsmouth, a short walk from downtown restaurants, shops, and museums. It's a quiet area, perfect for a relaxing getaway. The apartment has consistently received very good ratings from guests.
This two-bedroom, two-bathroom apartment can comfortably accommodate up to seven guests. Amenities include a fully equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a terrace or balcony, a garden, and internet access.

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.

Pennys Palace 1 Bed/1 Bath Home - Chesapeake, VA
9.7 163 reviews

Pennys Palace 1 Bed/1 Bath Home

apartment, Portsmouth
Penny's Palace, a private bungalow in a quiet Portsmouth, Virginia neighborhood, offers easy access to Olde Towne Portsmouth, the Children's Museum of Virginia, Downtown Norfolk, and Virginia Beach casinos.
This one-bedroom, one-bathroom guesthouse sleeps two comfortably and features a full kitchen with a fridge, freezer, microwave, and dishwasher, plus a private outdoor sitting area with a grill and access to a fitness center and parking.
Trycams Humble Abode - Chesapeake, VA
9.3 49 reviews

Trycams Humble Abode

apartment, Chesapeake
This Chesapeake home is conveniently located within a short drive of Virginia Beach, museums, Busch Gardens, Rivers Casino, and the Virginia Aquarium. The property has received excellent ratings for cleanliness and user experience, along with a very good location rating.
This family-friendly house comfortably sleeps eight guests in its three bedrooms. The home is fully equipped with a kitchen, laundry facilities, and entertainment options, making it a great choice for families or groups looking for a comfortable and convenient stay.
Modern 2 Bdrm Home W/firepit, Game Console, Bikes - Chesapeake, VA
9.7 62 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.
Luxury Lakefront Estate & Guest House W/ Pool - Chesapeake, VA
10 8 reviews

Luxury Lakefront Estate & Guest House W/ Pool

apartment, Portsmouth
This luxurious lakefront estate sits on Crystal Lake, offering stunning views and a peaceful escape just a short drive from the bustling city of Portsmouth. The property consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
This spacious home has six bedrooms and six bathrooms, comfortably accommodating up to sixteen guests. Enjoy the gourmet kitchen, private pool, and expansive grounds, perfect for both relaxing and entertaining.

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.

Lovely Two Bedroom, 1 1/2 Bath, King Bed Townhouse - Chesapeake, VA
9.9 131 reviews

Lovely Two Bedroom, 1 1/2 Bath, King Bed Townhouse

apartment, Portsmouth
The Pad On Liston - Chesapeake, VA
8.9 30 reviews

The Pad On Liston

apartment, Portsmouth
Beautiful Historic Apartment - Chesapeake, VA
10 12 reviews

Beautiful Historic Apartment

apartment, Norfolk
Cozy Cottage W/loft, Wifi, Workspace, Near Casino - Chesapeake, VA
9.6 59 reviews

Cozy Cottage W/loft, Wifi, Workspace, Near Casino

apartment, Portsmouth

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.

Tudor Treasure In Olde Towne - Chesapeake, VA
10 46 reviews

Tudor Treasure In Olde Towne

apartment, Portsmouth

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 5 Sleeps 4 - Chesapeake, VA
No reviews

Sojourn At Colley Manor Unit 5 Sleeps 4

apartment, Norfolk
Sojourn At Colley Manor Unit 1 Sleeps 4 - Chesapeake, VA
No reviews

Sojourn At Colley Manor Unit 1 Sleeps 4

apartment, Norfolk
Lovely 2-bedroom 1100 Sq Ft Apt With Free Parking - Chesapeake, VA
9.4 322 reviews

Lovely 2-bedroom 1100 Sq Ft Apt With Free Parking

apartment, Portsmouth
Chesapeake Comfort - Chesapeake, VA
9.3 8 reviews

Chesapeake Comfort

apartment, Chesapeake

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.

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
The Mermaids Lair ‍️ - Chesapeake, VA
9.0 14 reviews

The Mermaids Lair ‍️

apartment, Portsmouth
Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth - Chesapeake, VA
8.4 9 reviews

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

apartment, Portsmouth
Experience Timeless Luxury At Cavalier Manor On A Lake - Chesapeake, VA
9.6 10 reviews

Experience Timeless Luxury At Cavalier Manor On A Lake

apartment, Portsmouth

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.

Neon Wonderland, Sleeps 14, Hot Tub/pool/mini Golf - Chesapeake, VA
10 4 reviews

Neon Wonderland, Sleeps 14, Hot Tub/pool/mini Golf

apartment, Portsmouth
Wooded Wonderland - Chesapeake, VA
9.6 15 reviews

Wooded Wonderland

apartment, Portsmouth
Gorgeous 1 Bedroom With Free Wifi & Street Parking - Chesapeake, VA
8.0 1 review

Gorgeous 1 Bedroom With Free Wifi & Street Parking

apartment, Chesapeake
Free Breakfast. Indoor Pool & Hot Tub. Close To The Virginia Beach Business District! - Chesapeake, VA
8.0 4 reviews

Free Breakfast. Indoor Pool & Hot Tub. Close To The Virginia Beach Business District!

apartment, Chesapeake
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