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

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.
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.
Riverfront Portsmouth Home Near Casino & Patio - Chesapeake, VA
9.7 38 reviews

Riverfront Portsmouth Home Near Casino & Patio

apartment, Portsmouth
This Portsmouth waterfront house, located approximately 1.3 km from the Rivers Casino and 0.8 km from Historic Old Towne, offers stunning Elizabeth River views and private patio access.
Sleeping up to 10 guests, this three-bedroom, two-and-a-half-bathroom property boasts a fully equipped kitchen, high-speed Wi-Fi, and family-friendly amenities including a travel cot and high chair; nearby attractions include the Portsmouth Waterfront.
A Quiet Lakeside Home For Family, Business, Or Both To Relax Or Be Productive. - Chesapeake, VA
8.4 25 reviews

A Quiet Lakeside Home For Family, Business, Or Both To Relax Or Be Productive.

apartment, Virginia Beach
This four-bedroom, three-bathroom house in Virginia Beach is situated in a quiet cul-de-sac, approximately 48km from the beach, 27km from Naval Station Norfolk (NOB), and 19km from Naval Air Station Oceana.
The property, sleeping eight guests, offers a dedicated office space, lake views, and amenities including coffee, soap, and laundry pods; nearby attractions include the Veterans United Home Loans Amphitheatre and Greenbrier Mall.

Best Chesapeake, VA holiday apartments with a balcony

Boutique Private 2nd Floor 2br Apartment  W/d  Near Casino & Downtown - Chesapeake, VA
No reviews

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

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.
Nyakio Suite - Chesapeake - Chesapeake, VA
No reviews

Nyakio Suite - Chesapeake

apartment, Chesapeake
This two-bedroom flat is located in Chesapeake's Greenbrier district, a 7-minute walk from Rivercrest Play Area and a 10-minute walk from Dominion Marketplace.
This 101 square metre residence accommodates up to four guests, featuring a fully equipped kitchen, air conditioning, Wi-Fi, a balcony, and access to an on-site swimming pool and parking.
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.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews

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

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.

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

Portsmouth Monthly Apt. (1733-b) - Chesapeake, VA
8.5 8 reviews

Portsmouth Monthly Apt. (1733-b)

apartment, Portsmouth
This Portsmouth apartment is situated less than 0.8km from the Interstate and the Downtown Tunnel to Norfolk, offering easy access to major transport links.
The two-bedroom, one-bathroom flat sleeps four guests and boasts a fully equipped kitchen with dishwasher, in-unit laundry, a 55-inch TV, and high-speed Wi-Fi; ideal for short-term stays in the area.
Cozy Chesapeake Retreat W/ Flex Room - Chesapeake, VA
No reviews

Cozy Chesapeake Retreat W/ Flex Room

apartment, Chesapeake
This furnished two-bedroom flat in Chesapeake provides easy access to Greenbrier Mall and Veterans United Home Loans Amphitheater, situated just a short drive from Norfolk and Virginia Beach.
This accommodation offers a bonus flex room, a dedicated exercise/play room, 1.5 bathrooms, fast Wi-Fi, an in-home washer and dryer, and ample parking on a spacious plot.
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.
The Calm Cottage | European Fireplace Retreat - Chesapeake, VA
10 8 reviews

The Calm Cottage | European Fireplace Retreat

apartment, Chesapeake
This countryside cottage near Chesapeake offers peaceful rural views and is within a 40-48 kilometre drive of Virginia Beach Oceanfront and Sandbridge Beach, with the Outer Banks (Nags Head) accessible within approximately 20 kilometres for a longer day trip.
This two-bathroom apartment accommodates up to five guests across three bedrooms, each featuring a television and massage recliner, and includes a fully equipped kitchen, a private deck, and an in-home washer and dryer for convenience.

Best Chesapeake, VA holiday apartments with air conditioning

The Birds Nest - Chesapeake, VA
9.8 65 reviews

The Birds Nest

apartment, Chesapeake
This apartment is located in the Great Bridge area of Chesapeake, just 32 kilometres from the oceanfront, 8 kilometres from the interstate, and 10 kilometres from Greenbriar Mall, offering a peaceful retreat with a country feel despite its proximity to urban amenities. The property has received excellent ratings for location, cleanliness, and user experience.
The self-catering property can accommodate up to 8 guests and boasts a spacious outdoor area with a large fenced yard and an open field. It also features a tree house, a gazebo with an extension cord for lighting, and a variety of amenities including a Jacuzzi, a garden, and parking.
Condo ∙ 1 Bedroom ∙ 6 Guests - Chesapeake, VA
No reviews

Condo ∙ 1 Bedroom ∙ 6 Guests

apartment, Chesapeake
This apartment is conveniently located near the Virginia Beach business district and General Dynamics in Chesapeake, a 40-kilometre drive from the Virginia Beach oceanfront. The surrounding area offers easy access to both business and leisure activities, making it a popular choice for travellers.
This one-bedroom apartment can accommodate up to six guests comfortably, with two queen beds and a sofa bed. Guests can enjoy a range of amenities, including a fully equipped kitchen, a swimming pool, a hot tub, a fitness centre, and free parking.
3br Pet-friendly Retreat | Near Rivers Casino - Chesapeake, VA
9.7 66 reviews

3br Pet-friendly Retreat | Near Rivers Casino

apartment, Portsmouth
This Portsmouth, Virginia house rental is situated in the Craddock neighbourhood, a short drive from Portsmouth city centre and the Rivers Casino.
The three-bedroom property, sleeping up to six guests, boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, parking, and excellent Wi-Fi; nearby attractions include Norfolk and Virginia Beach, accessible by car (distances vary).
Portsmouth 2br/1ba Getaway - Chesapeake, VA
10 2 reviews

Portsmouth 2br/1ba Getaway

apartment, Portsmouth
This Portsmouth holiday home is situated within 4.8km of attractions including the Commodore Theatre, the Virginia Sports Hall of Fame and Museum, and the Children's Museum of Virginia.
The 102 square metre property sleeps six guests and boasts two bedrooms, one bathroom, a fully equipped kitchen, garden, parking, and a smoke-free environment.
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