Best apartment offers in Chesapeake, VA

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Chesapeake, VA apartments
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790 Holiday apartments 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

Coastal Comfort | Steps From Virginia Beach's Best - Chesapeake, VA
8.6 30 reviews

Coastal Comfort | Steps From Virginia Beach's Best

apartment, Virginia Beach
This Virginia Beach guesthouse, available for short-term lets from 1 February 2025, is situated in a residential area of Virginia Beach, its precise location and distance from the beach and boardwalk requiring further clarification.
Offering three bedrooms, one bathroom, and sleeping up to three guests, this fully furnished property includes a kitchen with fridge, freezer, microwave, and dishwasher, plus modern amenities such as central air conditioning, hardwood floors, and a washer/dryer; all utilities are included.
Kene's Luxury Retreat Near Va Beach+free Parking. - Chesapeake, VA
9.5 28 reviews

Kene's Luxury Retreat Near Va Beach+free Parking.

apartment, Portsmouth
This family-friendly, three-bedroom, two-storey residence is located in a residential area of Portsmouth, providing convenient access to local attractions such as the Historic Dockyard, approximately 3.5 kilometres away, without being in the immediate city centre.
This comfortable abode offers Wi-Fi, air conditioning, and parking, with a kitchen equipped with a freezer and dishwasher, accommodating up to eight guests and featuring a spacious backyard ideal for relaxation.
Escape To The Water! - Chesapeake, VA
9.9 27 reviews

Escape To The Water!

apartment, Portsmouth
This Portsmouth holiday home, located near the waterfront, offers easy access to attractions such as Prescott Park and Strawbery Banke Museum, though the precise distance is unspecified.
The two-bedroom, two-bathroom property sleeps six, features a fully equipped kitchen, air conditioning, parking, and internet access; guests can also enjoy lake access and two porches.
Prime Location In Chesapeake + Spacious 4br + Chef's Kitchen - Chesapeake, VA
9.4 9 reviews

Prime Location In Chesapeake + Spacious 4br + Chef's Kitchen

apartment, Chesapeake
This spacious four-bedroom flat in the Greenbrier district of Chesapeake is located approximately 40 kilometres from Virginia Beach, offering convenient access to Greenbrier Mall and Waterside District for shopping, as well as the Veterans United Home Loans Amphitheater for entertainment.
This family-friendly residence spans 186 square metres and accommodates up to eight guests, featuring a dedicated home theatre with a popcorn maker, a master suite with double vanities and a soaking tub, air conditioning, a garden, and parking.

Best Chesapeake, VA holiday apartments with a balcony

Historic Old Towne Southern Charm - Chesapeake, VA
9.4 44 reviews

Historic Old Towne Southern Charm

apartment, Portsmouth
This charming 2-bedroom flat is located in Old Towne Portsmouth, just a short walk from the city's restaurants, shops, and attractions. The area is known for its historic architecture and lively atmosphere, making it a great base for exploring the city. The apartment has a very good user rating, indicating a positive experience for previous guests.
This spacious home can comfortably accommodate up to 7 guests. It features a well-equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a terrace, and a garden. Guests can also enjoy free Wi-Fi and the convenience of a washing machine 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 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.
Nyakio Suite - Chesapeake, VA
No reviews

Nyakio Suite

apartment, Chesapeake
The Nyakio Suite is a 2-bedroom flat in Chesapeake, located 17.7 to 33.8 kilometres from Topgolf Virginia Beach, Mount Trashmore Park, and the King Neptune Statue on the Boardwalk.
This 102 square metre residence offers air conditioning, free WiFi, a fully equipped kitchen with a dishwasher and microwave, and can accommodate up to 7 guests, with a private swimming pool available for use.
Lovely Town Home - Chesapeake, VA
9.6 68 reviews

Lovely Town Home

apartment, Virginia Beach
This Virginia Beach house is located just 1.8 kilometres from Mount Trashmore Park, offering a peaceful escape from the city bustle, yet remaining within easy reach of the Virginia Beach Town Center and the Sandler Center for the Performing Arts. The property enjoys excellent guest ratings, highlighting its appeal for travellers.
This spacious home has four bedrooms and two bathrooms, comfortably accommodating up to ten guests. The house offers a range of amenities including a swimming pool, a jacuzzi, a garden, a terrace and parking, making it ideal for a relaxing and enjoyable stay.

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 great place to learn about the region's maritime history. You could also visit the Great Bridge Battlefield and National Monument, which commemorates a key battle in the American Revolution.
  • 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. It's also home to a large and diverse population, with a rich history and culture.
  • 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.

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

    Chesapeake has a public bus system, Hampton Roads Transit (HRT), which provides service throughout the city. However, it's important to note that it's not as extensive as in larger cities, and you might need to rely on a car for some trips.
  • 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.

  • 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 year in the fall. You might also enjoy the Chesapeake Arts Festival, which takes place in the summer and features live music, art exhibits, and food vendors.
  • What are the best apartments for families and kids in Chesapeake, VA?

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

    Apartments in Chesapeake typically include basic amenities like central air conditioning, a refrigerator, a stove, and a dishwasher. Some newer apartments might also have in-unit laundry facilities, a balcony, and a parking space.
  • What are the best pet friendly apartments in Chesapeake, VA?

  • What leisure activities are available for relaxation in Chesapeake, VA?

    Chesapeake offers a variety of leisure activities, including walking or cycling along the Chesapeake Bay Trail, visiting the Chesapeake Arboretum, or enjoying a round of golf at one of the many golf courses in the city.
  • What are the best apartments with parking in Chesapeake, VA?

Popular destinations

Best Chesapeake, VA holiday apartments with parking

Simply Amazing In Chesapeake - Chesapeake, VA
10 40 reviews

Simply Amazing In Chesapeake

apartment, Chesapeake
This Chesapeake property is conveniently located just 5-10 kilometres from Greenbrier Mall, various shopping plazas, and restaurants, making it a great base for exploring the area. It also enjoys a prime position, being only 15 kilometres from the Virginia Beach oceanfront and 10 kilometres from Ocean View in Norfolk. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
This spacious home offers three bedrooms and two bathrooms, comfortably accommodating up to eight guests. The fully equipped kitchen features a fridge, freezer, microwave, and dishwasher, alongside a garden, parking, air conditioning, and internet access, ensuring a comfortable and enjoyable stay.
Cozy Portsmouth Retreat 2br/1ba - Chesapeake, VA
9.0 2 reviews

Cozy Portsmouth Retreat 2br/1ba

apartment, Portsmouth
This Portsmouth apartment, ideally located for exploring the city, is a short 6.4km drive from the Children's Museum of Virginia and 8km from the Portsmouth Naval Shipyard Museum.
The 102 square metre property sleeps six guests and boasts two bedrooms, one bathroom, a fully equipped kitchen, in-unit laundry, air conditioning, parking, and Wi-Fi; nearby attractions include the Waterside District and Virginia Beach Town Centre.
Cozy Retreat - Chesapeake, VA
9.6 119 reviews

Cozy Retreat

apartment, Portsmouth
This Portsmouth apartment at 943 Hamilton Avenue is situated in a peaceful neighbourhood, offering convenient access to various attractions, although precise distances aren't specified.
The two-bedroom, one-bathroom flat sleeps five guests and includes a kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and excellent guest reviews.
Cozy Ranch Retreat. - Chesapeake, VA
9.4 35 reviews

Cozy Ranch Retreat.

apartment, Chesapeake
This stylish three-bedroom apartment is located in a central area, just a short drive from downtown Norfolk, Portsmouth Rivers Casino, and Virginia Beach, all within 30 kilometres. The property has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The apartment is spacious and welcoming, ideal for families or groups of up to six people. It includes a fully equipped kitchen, a comfortable living space, and a private garden, as well as access to a fitness centre and parking.

Best Chesapeake, VA holiday apartments with air conditioning

Old World Charm - Chesapeake, VA
9.9 99 reviews

Old World Charm

apartment, Portsmouth
This charming flat is located in historic Olde Town Portsmouth, within easy walking distance of the city's top attractions like the Strawbery Banke Museum and Prescott Park. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The flat offers a spacious layout with a living room, kitchenette, two bathrooms, and a bedroom that can sleep two guests. Enjoy a comfortable stay with amenities such as air conditioning, a private garden, and on-site parking, all within a historic building that adds a unique touch to your Portsmouth experience.
Free Breakfast. Indoor Pool & Hot Tub. Near The Virginia Beach Business District! - Chesapeake, VA
No reviews

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

apartment, Chesapeake
This Chesapeake condo is situated a 9-minute walk from the Chesapeake Conference Centre and a 3-minute drive (approximately 1.6 km) from Greenbrier Mall, offering easy beach access.
The one-bedroom, one-bathroom apartment sleeps four guests and includes a fully equipped kitchen, in-unit laundry, a swimming pool, jacuzzi, and free Wi-Fi; nearby attractions include the Veterans United Home Loans Amphitheatre and Waterside District.
Nyakio Suite - Chesapeake, VA
No reviews

Nyakio Suite

apartment, Chesapeake
This Nyakio Suite flat is situated on the first floor in a quiet family district of Chesapeake, Virginia, offering a tranquil retreat.
This pet-friendly residence accommodates up to four guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a decorative fireplace, and a private balcony overlooking a seasonal shared swimming pool, with internet and laundry facilities available.
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.
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