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

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home - Chesapeake, VA
9.3 148 reviews
Chesapeake, VA
31/07 – 03/08
SG$389/nighttotal: SG$1167 (3 )

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

4 2
apartment , Portsmouth
This Portsmouth apartment is located in a peaceful, historic neighbourhood, just a short distance from the city centre, the Elizabeth River and the beach. The property has been consistently rated excellent for location, cleanliness and overall experience.
The apartment is a spacious three-bedroom property that can comfortably accommodate up to seven guests. It offers a fully equipped kitchen, modern amenities such as high-speed Wi-Fi and a spa, as well as parking and a private entrance.
Chesapeake. Comfy  & Cozy. 4 Beds 2 Bath - Chesapeake, VA
9.4 78 reviews
Chesapeake, VA
25/09 – 30/09
SG$248/nighttotal: SG$1240 (5 )

Chesapeake. Comfy & Cozy. 4 Beds 2 Bath

1 2
apartment , Chesapeake
This three-bedroom apartment is situated in a peaceful area of Chesapeake, just 3km from Rivers Casino, 7km from Downtown Portsmouth, and 10km from Downtown Norfolk Waterside. The property has received excellent ratings for location, cleanliness, and user satisfaction.
The apartment offers plenty of space for families or groups of friends, comfortably accommodating up to six guests. It features a well-equipped kitchen, air conditioning, a garden, parking, and internet access, as well as being pet-friendly.
The Point! Private Waterfront  Oasis! - Chesapeake, VA
9.9 129 reviews
Chesapeake, VA
08/07 – 13/07
SG$1178/nighttotal: SG$5890 (5 )

The Point! Private Waterfront Oasis!

1 5
apartment , Norfolk
This Norfolk holiday home, ideally situated near Virginia Beach, offers easy access to Oceanview Beach and attractions such as Rivers Casino and the Waterside District, with distances to these locations needing clarification.
Sleeping up to 10 guests in four bedrooms and two bathrooms, this self-catering property boasts a fully equipped kitchen, air conditioning, a garden, fitness centre, parking, and excellent guest reviews, promising a comfortable stay.
Cambridge Knights A 3 Bedroom Home Full Of Charm - Chesapeake, VA
10 1 review
Chesapeake, VA
16/08 – 27/08
SG$344/nighttotal: SG$3784 (11 )

Cambridge Knights A 3 Bedroom Home Full Of Charm

3 4
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.

Best Chesapeake, VA holiday apartments with a balcony

Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
10 1 review
Chesapeake, VA
12/10 – 18/02
SG$231/nighttotal: SG$29799 (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.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews
Chesapeake, VA
16/08 – 27/08
SG$368/nighttotal: SG$4048 (11 )

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

4 4
apartment , Portsmouth
This holiday home is located in Portsmouth, just 1.5 km from Rivers Casino Portsmouth, and within 10 km of Portsmouth City Park and Frank D Lawrence Stadium. It has consistently received excellent user ratings, making it a popular choice for travellers.
The property offers 93 square metres of space and can comfortably accommodate up to 6 guests in its 3 bedrooms. The kitchen comes equipped with a fridge, microwave, oven, and dishwasher, while the garden provides a relaxing outdoor space. Guests can also enjoy free Wi-Fi, air conditioning, a terrace, and parking.
Charming 2 Br Vintage Duplex Upstairs Apartment In Historic Portsmouth Ac & Wifi - Chesapeake, VA
9.0 7 reviews
Chesapeake, VA
25/09 – 30/09
SG$270/nighttotal: SG$1350 (5 )

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

2 2
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.
Lovely Town Home - Chesapeake, VA
9.6 68 reviews
Chesapeake, VA
12/10 – 18/02
SG$286/nighttotal: SG$36894 (129 )

Lovely Town Home

4 2
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?

Destinations nearby

Best Chesapeake, VA holiday apartments with parking

Home Away From Home - Chesapeake, VA
9.8 21 reviews
Chesapeake, VA
27/06 – 30/06
SG$359/nighttotal: SG$1077 (3 )

Home Away From Home

1 3
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.
Spacious 5-bedroom House With Ac In Beautiful Portsmouth - Chesapeake, VA
8.0 2 reviews
Chesapeake, VA
31/07 – 31/08
SG$822/nighttotal: SG$25482 (31 )

Spacious 5-bedroom House With Ac In Beautiful Portsmouth

5 2
apartment , Portsmouth
This five-bedroom house in Portsmouth, VA, is located in the central district of Historic Downtown, offering proximity to shops, restaurants, cultural attractions, and the waterfront, with the Hill House Museum and United States Lightship Portsmouth within walking distance.
This spacious property accommodates up to 18 guests with five bedrooms, three bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, garden, spa, and on-site parking, making it ideal for larger groups seeking self-catering options near MacArthur Center and the Waterside District.
Experience Timeless Luxury At Cavalier Manor On A Lake - Chesapeake, VA
9.6 10 reviews
Chesapeake, VA
01/12 – 29/12
SG$1886/nighttotal: SG$52808 (28 )

Experience Timeless Luxury At Cavalier Manor On A Lake

5 2
apartment , Portsmouth
This five-bedroom, five-bathroom property, Cavalier Manor, is a 557 square metre estate located in Portsmouth, Virginia, a short drive from the beaches of Virginia Beach and the city of Norfolk. This spacious home offers a private pool, a fully equipped outdoor kitchen, and elegant fireplaces throughout, making it ideal for families or groups of up to 15 guests.
5 Minutes To The Casino!family Sized Home 3 Bedroom With Patio And A Game Room - Chesapeake, VA
9.6 170 reviews
Chesapeake, VA
25/09 – 30/09
SG$288/nighttotal: SG$1440 (5 )

5 Minutes To The Casino!family Sized Home 3 Bedroom With Patio And A Game Room

3 4
apartment , Portsmouth
This Portsmouth apartment is conveniently located just four minutes from Rivers Casino and fifteen minutes from the Waterside District, offering easy access to a range of attractions. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The three-bedroom flat, spanning 130 square metres, comfortably sleeps up to eight guests. It boasts a fully equipped kitchen, a garden, a spa, a tennis court, and a range of entertainment options, including a pool table, darts, and a fire pit.

Best Chesapeake, VA holiday apartments with air conditioning

Mid-century Modern Old Town Portsmouth 3bd/2.5 Bth - Chesapeake, VA
9.9 132 reviews
Chesapeake, VA
25/09 – 30/09
SG$351/nighttotal: SG$1755 (5 )

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

3 4
apartment , Portsmouth
This charming house is located on a quiet street in Colonial Portsmouth, just a few hundred metres from the waterfront and next to a park. It has excellent user, location and cleanliness ratings, making it a great choice for a stay in Portsmouth.
The house has a spacious open-plan kitchen, dining and living area, perfect for families or groups of up to six people. The house is fully equipped with amenities including a kitchen, multiple bathrooms, a garden, parking and air conditioning, making it a comfortable and convenient place to stay.
Olde Towne, Historic, Location! - Chesapeake, VA
9.6 49 reviews
Chesapeake, VA
31/07 – 03/08
SG$223/nighttotal: SG$669 (3 )

Olde Towne, Historic, Location!

2 2
apartment , Portsmouth
This charming two-bedroom flat is located in Olde Towne Portsmouth, just a short walk from restaurants, a cinema, coffee shops, and the ferry to Norfolk. The property has received excellent ratings for its location, cleanliness, and overall experience.
The flat is spread over three floors and comfortably accommodates three guests. It features a fully equipped kitchen, a private office, a peaceful porch with a view of the trees and church towers, and a charming historic atmosphere.
Best Location In Olde Towne Portsmouth - Chesapeake, VA
9.9 130 reviews
Chesapeake, VA
31/07 – 31/08
SG$99/nighttotal: SG$3069 (31 )

Best Location In Olde Towne Portsmouth

1 2
apartment , Portsmouth
This charming flat is situated in the historic Old Towne district of Portsmouth, Virginia, just a short walk from the Naval Medical Center and the ferry terminal to downtown Norfolk. It has received excellent ratings for its location, cleanliness and overall experience.
The apartment has one bedroom and one bathroom, comfortably accommodating two guests. It features a well-equipped kitchen, a private patio, central heating and air conditioning, a TV with basic cable, and Wi-Fi access.
Sojourn At Colley Manor Unit 4 - Chesapeake, VA
Chesapeake, VA
01/07 – 31/07
SG$198/nighttotal: SG$5940 (30 )

Sojourn At Colley Manor Unit 4

2 2
apartment , Norfolk
Colley Manor Unit 4, a two-bedroom flat in Norfolk, is situated 10.6 km from the Norfolk Botanical Garden and 14.3 km from Topgolf Virginia Beach.
This 93 square metre self-catering apartment sleeps six, boasting a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, free Wi-Fi, and parking.
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