Best apartment offers in Chesapeake, VA

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Chesapeake, VA apartments
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790 Best apartments in Chesapeake, VA

Best family friendly Chesapeake, VA Holiday Apartments and Self Catering Accommodations

Among the 790 accommodations in Chesapeake, VA, here are the 4 best family friendly holiday apartments

3br Gem Near Rivers Casino | Comfort & Convenience - Chesapeake, VA
9.6 34 reviews

3br Gem Near Rivers Casino | Comfort & Convenience

apartment, Portsmouth
This Portsmouth apartment is conveniently located just a short distance from Norfolk and Virginia Beach, making it an ideal base for exploring the region. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The spacious apartment has three bedrooms and one bathroom, comfortably accommodating up to six guests. The apartment offers a range of amenities, including a fully equipped kitchen, laundry facilities, air conditioning, parking, and internet access, ensuring a comfortable and convenient stay.
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
This one-bedroom flat in Portsmouth is situated a 19-minute drive from Town Point Park and 40 minutes from Chesapeake Bay, offering convenient access to the Chrysler Museum of Art and the Children's Museum of Virginia.
This pet-friendly apartment accommodates up to three guests and includes on-site parking, complimentary Wi-Fi, air conditioning, and essential amenities such as towels, linens, and soap, with a check-out time of 12:00.
The Manor- Extended Stays - Chesapeake, VA
10 8 reviews

The Manor- Extended Stays

apartment, Chesapeake
This Chesapeake apartment, near Greenbrier Mall, offers easy access to the Oceanfront, Norfolk Waterside, and Norfolk Outlets.
The four-bedroom, two-bathroom property sleeps eight, features a recently remodelled kitchen with modern appliances, a 65-inch TV, free Wi-Fi, and self check-in; nearby attractions include the Chesapeake Jubilee and Deep Creek Locks.
Cozy Home W/ Flex Room & Large Driveway - Chesapeake, VA
8.0 1 review

Cozy Home W/ Flex Room & Large Driveway

apartment, Virginia Beach
This Chesapeake flat is located in a peaceful residential area, a short drive from shopping, dining, major motorways, and Blue Heron Landing Park, which offers access to the Indian River for kayaking, fishing, and crabbing.
This fully furnished two-bedroom property accommodates up to six guests and features a versatile flex room, a separate exercise/play room, fast WiFi, smart TVs, and an in-unit washer and dryer, with ample parking available.

Best Chesapeake, VA holiday apartments with a balcony

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 holiday home is located just 3km from attractions like the Emanuel AME Church, Commodore Theatre, and the Virginia Sports Hall of Fame and Museum, making it a great base for exploring the city. The surrounding area is quiet and residential, offering a peaceful escape from the hustle and bustle of the city centre.
The property has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It features a fully equipped kitchen, a terrace or balcony, a spa, and free parking, as well as modern amenities like Wi-Fi and air conditioning.
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 spacious four-bedroom flat in Portsmouth is situated conveniently for recreational parks and attractions, a mere 1.9 kilometres from the Norfolk Scope and Waterside District.
Offering 186 square metres of living space for up to eight guests, this residence features a private terrace, air conditioning, complimentary Wi-Fi, and a fully equipped kitchen, with on-site parking also provided.
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 apartment, a short walk from the Commodore Theatre and the Virginia Sports Hall of Fame, enjoys a riverfront location offering scenic views and is within 2.4km of the Children's Museum of Virginia and the Portsmouth Naval Shipyard Museum.
The two-bedroom, one-bathroom flat sleeps four, features free WiFi, a DVD player, a fully equipped kitchen, on-site parking, and a terrace; board games and books are also provided for guests' entertainment.
Charming 1-bedroom 1-bath Unit With Beautiful Riverfront Sunsets In Portsmouth - Chesapeake, VA
9.8 9 reviews

Charming 1-bedroom 1-bath Unit With Beautiful Riverfront Sunsets In Portsmouth

apartment, Portsmouth
This Portsmouth waterfront apartment, situated near Bon Secours Maryview Hospital (within 8km), offers easy access to the city's naval bases and the Waterside District.
The one-bedroom flat sleeps two, includes a full kitchen with dishwasher, in-unit laundry, smart TVs, a terrace, and free off-street parking, plus nearby access to a tree swing and shared porch.

Frequently asked questions about apartment rentals in Chesapeake, VA

  • What makes Chesapeake, VA unique or famous?

    Chesapeake is known for its beautiful waterfront, with access to the Chesapeake Bay and its tributaries. It's also a city with a rich history, having played a significant role in the American Revolution.
  • Where can you find the best local markets and street food in Chesapeake, VA?

    The Chesapeake Farmers Market, held on Saturdays at the Chesapeake City Park, is a great place to find local produce and crafts. For street food, the food trucks at the Greenbrier Mall food court offer a variety of options.
  • How is the public transportation system in Chesapeake, VA?

    Chesapeake has a public transportation system called Hampton Roads Transit (HRT), offering bus services throughout the city. However, for getting around the wider area, you'll likely need a car.
  • Which seasonal events or festivals should apartment renters look forward to in Chesapeake, VA?

    The Chesapeake Bay Wine Festival in the spring is a popular event, showcasing local wineries. The Chesapeake Bay Seafood Festival in the autumn celebrates the region's seafood bounty.
  • What amenities are typically included in apartments in Chesapeake, VA?

    Most apartments in Chesapeake include central air conditioning, a washer and dryer, and a dishwasher. Some newer buildings may offer additional amenities like a fitness center or a swimming pool.
  • What leisure activities are available for relaxation in Chesapeake, VA?

    Chesapeake offers plenty of opportunities for relaxation. You can enjoy the beaches at Chesapeake Bay, go for a walk or bike ride along the Chesapeake Bay Trail, or simply relax at one of the many parks in the city.

Popular destinations

Best Chesapeake, VA holiday apartments with parking

The Mermaids Lair ‍️ - Chesapeake, VA
9.3 153 reviews

The Mermaids Lair ‍️

apartment, Portsmouth
This charming guest house is situated just a short drive from Portsmouth, New Hampshire, offering easy access to the city's attractions while enjoying the peace and tranquility of Crystal Lake. The property has consistently received excellent ratings for its cleanliness, location, and overall guest experience.
The cosy house has one bedroom and one bathroom, comfortably accommodating up to two guests. Guests can enjoy stunning lake views, relax on the patio, or take advantage of the private dock and kayak access, as well as other amenities like a private fire pit and an automatic gate for added security.
Spacious 5 Bedroom W/ Pool And Patio Area. - Chesapeake, VA
10 3 reviews

Spacious 5 Bedroom W/ Pool And Patio Area.

apartment, Chesapeake
This four-bedroom house is centrally located in the Chesapeake district, providing convenient access to local attractions and amenities.
This spacious property accommodates up to eight guests and features a private swimming pool and a fitness centre, offering a comfortable and well-equipped base for your stay in Chesapeake.
Waterfront Home Near Va Beach | Sleeps 16+ | 5br - Chesapeake, VA
10 2 reviews

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

apartment, Norfolk
This five-bedroom, two-bathroom flat in Coastal Virginia offers waterfront views and is conveniently located within 5 kilometres of Virginia Beach and Naval Station Norfolk, providing easy access to local attractions and dining.
This spacious apartment accommodates up to 16 guests, featuring a kitchen with a fridge, air conditioning, Wi-Fi, and parking, with outdoor café lights enhancing the evening ambiance for family reunions or military graduations.
Serene Tree House Retreat | Spacious 1br/1bth Home - Chesapeake, VA
9.9 32 reviews

Serene Tree House Retreat | Spacious 1br/1bth Home

apartment, Chesapeake
The Magnolia Tree House is situated in a peaceful residential neighbourhood in Chesapeake, just 15km south of downtown Norfolk, and within easy reach of attractions like Virginia Beach Town Center (27km) and the Virginia Beach Boardwalk (48km). This apartment has received excellent user ratings for cleanliness and location, and a very good rating overall.
The one-bedroom flat can comfortably accommodate two guests, and features a spacious and cosy layout. Amenities include a fully equipped kitchen, a private terrace with a fire pit and grilling area, a fitness centre, and parking.

Best Chesapeake, VA holiday apartments with air conditioning

Longer Stays Welcome! King Bed, Queen Bed, W/d - Chesapeake, VA
9.9 51 reviews

Longer Stays Welcome! King Bed, Queen Bed, W/d

apartment, Portsmouth
This Portsmouth apartment, near numerous shops including Kroger, TJ Maxx, and Walmart, and less than 1.6km from the Rivers Casino, offers convenient access to amenities.
The recently renovated two-bedroom, one-bathroom property sleeps four guests and boasts a private patio, modern amenities such as a dishwasher and air conditioning, and a washer/dryer.
New R & R Lake House In Va Beach - Chesapeake, VA
9.9 34 reviews

New R & R Lake House In Va Beach

apartment, Virginia Beach
This spacious Virginia Beach house, ideally located in a central area offering easy access to the city's attractions, provides a convenient base for exploring the resort.
The four-bedroom, three-bathroom property sleeps ten guests and boasts a fully equipped kitchen with dishwasher, a jacuzzi, fitness centre, and a garden, plus parking and amenities such as a pool table and large TVs in each bedroom.
Ocean Haus - Chesapeake, VA
9.4 95 reviews

Ocean Haus

apartment, Portsmouth
This Portsmouth family home, located near Junction I-264 and less than 1.6km from the Rivers Casino, offers easy access to the city and surrounding areas.
Sleeping up to 10 guests in 3 bedrooms and 4 bathrooms, this spacious property boasts a fully equipped kitchen with dishwasher, air conditioning, a garden, parking, and excellent guest reviews; perfect for family groups.
Chesapeake Comfort - Chesapeake, VA
9.3 14 reviews

Chesapeake Comfort

apartment, Chesapeake
This Chesapeake flat is conveniently situated, offering a peaceful environment away from the city's hustle and bustle, ideal for both business travellers and families seeking a quiet stay.
This 3-bedroom, 2-bathroom abode accommodates up to 6 guests, featuring essential amenities such as air conditioning, parking, and a kitchen with a freezer and dishwasher, perfect for a comfortable and private visit.
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