Best apartment offers in Chesapeake, VA

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Chesapeake, VA apartments
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568 Holiday apartments Chesapeake, VA

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

Among the 568 accommodations in Chesapeake, VA, here are the 4 best family friendly holiday apartments

Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
10 1 review
Chesapeake, VA
12/10 – 18/02
156 €/nighttotal: 20124 € (129 )

Cheerful 2 Bedroom Home Near Virginia Wesleyan

2 2
apartment , Virginia Beach
This Northwest Virginia Beach holiday home is situated 0.5km from Virginia Wesleyan University, within 5km of Cypress Point Country Club, and less than 5km from Norfolk Premium Outlets.
This 89 square metre property offers two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen with oven and microwave, a private balcony, on-site barbecue grills, and in-unit laundry facilities.
Cozy Quarters Near Nmcp - Chesapeake, VA
Chesapeake, VA
14/08 – 16/08
170 €/nighttotal: 340 € (2 )

Cozy Quarters Near Nmcp

1 2
apartment , Portsmouth
This two-bedroom duplex flat is situated in Portsmouth, a short distance from the Naval Medical Center and surrounding shipyards, making it an ideal base for professionals working in the area.
This family-friendly accommodation offers a garden, air conditioning, and a kitchen equipped with a fridge and microwave, providing comfort for up to four guests with one bathroom.
3br, 6 Beds  Prime Stay Near Rivers Casino! - Chesapeake, VA
10 1 review
Chesapeake, VA
16/08 – 27/08
273 €/nighttotal: 3003 € (11 )

3br, 6 Beds Prime Stay Near Rivers Casino!

3 4
apartment , Portsmouth
This Portsmouth holiday home is situated within 5km of the Rivers Casino Portsmouth, the Commodore Theatre, and the Virginia Sports Hall of Fame, offering easy access to these attractions.
The three-bedroom property sleeps six guests and boasts a fully equipped kitchen with appliances including a dishwasher, a garden, parking, and free Wi-Fi, alongside a washing machine and barbecue facilities.
Comfortable Retreat W/ Backyard & Parking - Chesapeake, VA
9.3 85 reviews
Chesapeake, VA
23/06 – 25/06
170 €/nighttotal: 340 € (2 )

Comfortable Retreat W/ Backyard & Parking

2 3
apartment , Portsmouth
This two-bedroom duplex is situated just 500 metres from the Portsmouth Shipyard and a short drive from the city centre, offering easy access to attractions and amenities. The surrounding area is quiet and residential, providing a peaceful retreat after a day of exploring.
The apartment comfortably sleeps six guests and features a well-equipped kitchen, a comfortable living area, and a modern bathroom. Guests can enjoy the convenience of air conditioning, free Wi-Fi, and parking, as well as the added benefit of being pet-friendly.

Best Chesapeake, VA holiday apartments with a balcony

Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood. - Chesapeake, VA
Chesapeake, VA
31/07 – 31/08
245 €/nighttotal: 7595 € (31 )

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

1 2
apartment , Chesapeake
This one-bedroom flat is located in Chesapeake, just a short distance from Norfolk's waterfront and a 32-kilometre drive from Virginia Beach's oceanfront. The surrounding area is quiet and offers easy access to local restaurants, supermarkets, and the city centre.
The flat is spacious and comfortably accommodates up to four guests. It comes with free curbside parking, air conditioning, internet access, and a relaxing front porch.
Monthly, Dog-friendly Home At Orange Blossom - Chesapeake, VA
Chesapeake, VA
31/07 – 31/08
208 €/nighttotal: 6448 € (31 )

Monthly, Dog-friendly Home At Orange Blossom

3 2
apartment , Virginia Beach
This three-bedroom, four-bathroom apartment is situated in Virginia Beach's Green Run neighbourhood, approximately 24 kilometres from various beaches and close to Norfolk.
The self-catering property offers a spacious open-plan layout, sleeping up to five guests, and boasts a fully fenced backyard, on-site parking, and a fully equipped kitchen including a dishwasher; nearby attractions include Lynnhaven Mall, Landstown Commons, Town Centre, and Mount Trashmore Park.
Boutique Private 2nd Floor 2br Apartment  W/d  Near Casino & Downtown - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
95 €/nighttotal: 12255 € (129 )

Boutique Private 2nd Floor 2br Apartment W/d Near Casino & Downtown

2 2
apartment , Portsmouth
This private upstairs flat in historic Westhaven, Portsmouth, is conveniently located 4 kilometres from Rivers Casino, 2 kilometres from Portsmouth City Park, and offers proximity to the Commodore Theatre and Portsmouth Naval Shipyard Museum.
This two-bedroom apartment accommodates up to four guests, featuring a kitchenette, a full-size washer and dryer, air conditioning, internet, and private off-street parking for one vehicle.
Charming 2 Br Vintage Duplex Upstairs Apartment In Historic Portsmouth Ac & Wifi - Chesapeake, VA
9.0 7 reviews
Chesapeake, VA
25/09 – 30/09
182 €/nighttotal: 910 € (5 )

Charming 2 Br Vintage Duplex Upstairs Apartment In Historic Portsmouth Ac & Wifi

2 4
apartment , Portsmouth
This Portsmouth apartment is conveniently located near the Children's Museum of Virginia and the Portsmouth Naval Shipyard Museum, approximately 1.8 km away.
The two-bedroom, one-bathroom flat sleeps four guests and features a terrace, garden, fully equipped kitchen including oven, microwave and coffee maker, plus in-unit laundry facilities and free Wi-Fi.

Frequently asked questions about apartment rentals in Chesapeake, VA

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

    The Chesapeake City Park is home to the Great Bridge Battlefield and Memorial, a significant site from the American Revolution. The Chesapeake Arboretum is a great place to learn about the local flora and fauna, and the Chesapeake Bay Foundation's Brock Environmental Center has exhibits about the Chesapeake Bay's ecosystem. For a taste of local history, the Chesapeake Historical Society Museum offers a glimpse into the city's past.
  • What are the best apartments in Chesapeake, VA?

  • What makes Chesapeake, VA unique or famous?

    Chesapeake is known for its beautiful waterfront, with the Chesapeake Bay providing stunning views and opportunities for water activities. It is also a city with a rich history, with sites like the Great Bridge Battlefield and Memorial, a significant battleground from the American Revolution. Chesapeake is also known for its diverse population, with a mix of urban and suburban areas, offering a variety of lifestyles.
  • What are the best apartments with a pool in Chesapeake, VA?

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

    Chesapeake has a few farmers' markets, like the Chesapeake Farmers Market, where you can find local produce and crafts. For street food, you can try the food stalls at the Chesapeake City Park, especially during events. The Greenbrier area also has a few food trucks that pop up in different locations.
  • 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's public transportation system is primarily provided by Hampton Roads Transit (HRT). They offer buses that connect different parts of the city and nearby areas. However, it's worth noting that the system is not as extensive as in larger cities, so having a car is generally recommended for getting around Chesapeake.
  • 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 in the spring, offering tastings from local wineries. In the summer, the Chesapeake Bay Seafood Festival is a big draw, with fresh seafood and live music. The Chesapeake Fall Festival, held in October, is a great way to experience autumn with craft vendors and live entertainment.
  • What are the best pet friendly apartments in Chesapeake, VA?

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

    Apartments in Chesapeake usually include basic amenities like central air conditioning, a refrigerator, and a stove. Some apartments may also offer amenities like in-unit laundry, a dishwasher, or a balcony. It's best to check the specific listing for details.
  • What are the best apartments with parking in Chesapeake, VA?

Destinations nearby

Best Chesapeake, VA holiday apartments with parking

Steps To Elizabeth River & Dtwn! Portsmouth Condo - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
81 €/nighttotal: 10449 € (129 )

Steps To Elizabeth River & Dtwn! Portsmouth Condo

1 2
apartment , Portsmouth
This one-bedroom flat in Portsmouth is situated 8 minutes' walk from the Portsmouth Naval Shipyard Museum and 6 minutes' walk from the Commodore Theatre.
This 56 square metre apartment accommodates two guests and features a fully equipped kitchen, air conditioning, on-site parking, and internet access, with a coin-operated laundry facility conveniently located nearby.
Virginia Beach, Getaway - Chesapeake, VA
9.8 51 reviews
Chesapeake, VA
23/06 – 25/06
147 €/nighttotal: 294 € (2 )

Virginia Beach, Getaway

1 3
apartment , Virginia Beach
This modern one-bedroom apartment in Virginia Beach is situated on a quiet cul-de-sac, minutes from Lynnhaven Inlet, local shops, restaurants, and beaches, as well as the Virginia Beach Convention Center and sports facilities.
The self-catering flat offers two queen-size beds sleeping up to four guests, a fully equipped kitchen, in-unit laundry, and a newly fitted bathroom; enjoy easy access to the area's attractions.
Sojourn At Colley Manor Unit 2 - Chesapeake, VA
10 2 reviews
Chesapeake, VA
31/07 – 31/08
125 €/nighttotal: 3875 € (31 )

Sojourn At Colley Manor Unit 2

2 2
apartment , Norfolk
This Ghent flat in Norfolk is centrally located near Colley Avenue's restaurants and shops, within easy reach (by foot, bike, bus, or Tide light rail) of Norfolk city centre and major hospitals such as CHKD and Norfolk General Hospital, and a short drive (approximately 20-30 km) from Virginia Beach and Ocean View Beach.
This 93-square-metre (1000 sq ft) two-bedroom, one-bathroom apartment sleeps four, offering self-check-in, a fully equipped kitchen (including fridge, microwave, and dishwasher), air conditioning, parking, and internet access; pack 'n' play and high chair rentals are available for families.
Traveling Professional Condo - Chesapeake, VA
10 1 review
Chesapeake, VA
31/07 – 31/08
110 €/nighttotal: 3410 € (31 )

Traveling Professional Condo

1 2
apartment , Chesapeake
This Western Branch condo in Chesapeake offers a peaceful retreat, conveniently located near major cities including Norfolk, Newport News, Portsmouth, Suffolk, and Virginia Beach.
The two-bedroom apartment sleeps four, features a fully equipped kitchen with stainless steel appliances, in-unit laundry, smart TVs, and assigned parking, providing comfortable accommodation for families or professionals visiting the area.

Best Chesapeake, VA holiday apartments with air conditioning

Escape To A Waterfront Retreat - Chesapeake, VA
9.5 25 reviews
Chesapeake, VA
16/08 – 27/08
192 €/nighttotal: 2112 € (11 )

Escape To A Waterfront Retreat

3 4
apartment , Portsmouth
This three-bedroom, three-bathroom waterfront apartment in the Hampton Roads area offers easy access to Portsmouth, Norfolk, Virginia Beach, and Suffolk, all within a few kilometres' radius.
The self-catering property sleeps eight guests and boasts a private deck, dock, boat slip, ample parking, and air conditioning, perfect for exploring the local attractions and naval bases.
Home Away From Home - Chesapeake, VA
9.8 21 reviews
Chesapeake, VA
24/07 – 26/07
340 €/nighttotal: 680 € (2 )

Home Away From Home

1 4
apartment , Portsmouth
This Hampton Roads townhouse offers a convenient base for exploring Portsmouth, situated a short drive (precise distance unspecified) from Portsmouth's city centre and the Virginia Beach boardwalk.
The two-bedroom, two-bathroom property sleeps four guests and features a fully equipped kitchen, private backyard deck overlooking a river, and amenities including Wi-Fi, air conditioning, and parking.
Convenient To All 7 Cities - Chesapeake, VA
9.2 52 reviews
Chesapeake, VA
24/07 – 26/07
397 €/nighttotal: 794 € (2 )

Convenient To All 7 Cities

1 4
apartment , Chesapeake
This comfortable home in Chesapeake is conveniently located just a short distance from the Norfolk Waterside District, Rivers Casino, and Sentara/Obici Hospitals, making it a great base for exploring the area. It has received excellent ratings for location, cleanliness, and overall experience.
The house is spacious, with 176 square metres of living space and can accommodate up to six guests in its three bedrooms. It offers a fully equipped kitchen, a relaxing deck, and a private garden, perfect for enjoying a peaceful stay.
Cozy Portsmouth Getaway 2br/1ba - Chesapeake, VA
9.6 28 reviews
Chesapeake, VA
31/07 – 31/08
122 €/nighttotal: 3782 € (31 )

Cozy Portsmouth Getaway 2br/1ba

1 2
apartment , Portsmouth
This two-bedroom house, situated in Portsmouth, Virginia's Port Norfolk Historic District, offers convenient access to local attractions.
The property sleeps six, features a fully equipped kitchen with fridge and microwave, plus a backyard, air conditioning, high-speed Wi-Fi, and a washer/dryer.
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