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

Port Peaceful, Backyard, Cozy Beds! Family Ready - Chesapeake, VA
7.0 2 reviews

Port Peaceful, Backyard, Cozy Beds! Family Ready

apartment, Portsmouth
This two-bedroom flat in Portsmouth is located a mere 3-minute drive from both the Children's Museum of Virginia and the Portsmouth Naval Shipyard Museum, offering convenient access to local attractions.
This pet-friendly accommodation for up to eight guests features air conditioning, Wi-Fi, a full kitchen with an oven and microwave, a garden with a fire pit, and covered parking, with a barbecue and fireplace for added comfort.
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.
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home - Chesapeake, VA
8.2 45 reviews

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

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.
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.

Best Chesapeake, VA holiday apartments with a balcony

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.
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.
Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
No reviews

Cheerful 2 Bedroom Home Near Virginia Wesleyan

apartment, Virginia Beach
This private two-bedroom townhome is located on a corner cul-de-sac lot in the Northwest district of Virginia Beach, offering a quiet setting just a short drive to First Landing State Park and the Virginia Aquarium.
This 89 square meter residence accommodates up to four guests, featuring a fully equipped kitchen with a wine cooler, a screened-in porch, an extra-large sectional sofa, and high-speed WiFi, with contactless entry for a seamless self-check-in experience.
Welcome To The Lighthouse!  Charming  3-bdrm Home With 2 Decks In Virginia Beach - Chesapeake, VA
8.0 3 reviews

Welcome To The Lighthouse! Charming 3-bdrm Home With 2 Decks In Virginia Beach

apartment, Virginia Beach
This Virginia Beach holiday home, a lighthouse property, is situated 1.6km from Regent University and a short drive from the interstate, providing easy access to beaches, the Virginia Beach Town Centre, and the Greenbrier Mall.
Sleeping six guests, this three-bedroom, three-bathroom property offers a kitchen with fridge, microwave, and dishwasher, air conditioning, a terrace, garden, parking, and Wi-Fi; nearby attractions include the Veterans United Home Loans Amphitheatre and Ocean Breeze Waterpark.

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

11 Mi To Virginia Beach Boardwalk: Studio Retreat! - Chesapeake, VA
9.7 48 reviews

11 Mi To Virginia Beach Boardwalk: Studio Retreat!

apartment, Virginia Beach
This Virginia Beach studio apartment is situated approximately 1.6 kilometres from Virginia Beach Town Centre, offering easy access to the beach and attractions such as the Virginia Aquarium & Marine Science Center and First Landing State Park.
The self-catering unit sleeps two guests and features a kitchenette with microwave and mini-fridge, a smart TV, free Wi-Fi, and access to a shared backyard; keyless entry is provided.
Top Gun R&r Iv: 3 Bedrooms, 2 Baths, Sleeps 8. - Chesapeake, VA
10 2 reviews

Top Gun R&r Iv: 3 Bedrooms, 2 Baths, Sleeps 8.

apartment, Portsmouth
This spacious 3-bedroom flat in Portsmouth offers a tranquil setting with convenient access to local attractions, located a short distance from the historic Portsmouth Historic Dockyard.
With accommodation for up to 8 guests, this modern apartment features a bright, open-plan living area, a well-equipped kitchen with a dishwasher, luxury bathrooms, and a large backyard with hammocks and a fire pit, ideal for families or groups seeking comfort and outdoor space.
Home Away From Home - Chesapeake, VA
9.7 28 reviews

Home Away From Home

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.
Steps To Elizabeth River & Dtwn! Portsmouth Condo - Chesapeake, VA
No reviews

Steps To Elizabeth River & Dtwn! Portsmouth Condo

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.

Best Chesapeake, VA holiday apartments with air conditioning

Stylish Two Bdrm, 1 1/2 Bth, King Bed Townhouse - Chesapeake, VA
9.9 66 reviews

Stylish Two Bdrm, 1 1/2 Bth, King Bed Townhouse

apartment, Portsmouth
This two-bedroom apartment in Portsmouth is situated less than a mile from the new Rivers Casino, offering easy access to entertainment and dining options. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The property can comfortably accommodate up to four guests and features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. The apartment also benefits from air conditioning, a garden, and parking, ensuring a comfortable and convenient stay.
3 Bedrms 3 Beds 2 Baths Mins From Rivers Casino - Chesapeake, VA
No reviews

3 Bedrms 3 Beds 2 Baths Mins From Rivers Casino

apartment, Portsmouth
This Portsmouth flat is situated just off the I-264, placing it within 400 metres of the Rivers Casino and offering convenient access to the Norfolk/Virginia Beach metropolitan area.
This three-bedroom, two-bathroom apartment accommodates up to six guests and boasts amenities including air conditioning, a garden, parking, and a kitchen equipped with a fridge, microwave, and dishwasher, with major shopping centres, hospitals, museums, and the Norfolk Waterside all within easy reach.
Walk To River & Downtown: Portsmouth Apartment! - Chesapeake, VA
10 1 review

Walk To River & Downtown: Portsmouth Apartment!

apartment, Portsmouth
This Portsmouth apartment, near the Children's Museum of Virginia (a 0.9km walk) and the Portsmouth Naval Shipyard Museum (a 1.1km walk), offers convenient access to local attractions.
The 111-square-metre property comprises three bedrooms, one bathroom, and on-site parking, plus in-unit amenities including a washer/dryer, full kitchen, and air conditioning; BBQ facilities are also available.
Cowbell Cottage - Chesapeake, VA
9.7 39 reviews

Cowbell Cottage

apartment, Chesapeake
Cowbell Cottage, a three-bedroom Chesapeake countryside retreat, is situated a short drive from Chesapeake city centre, offering easy access to local amenities.
This self-catering property sleeps eight guests and boasts a kitchen, air conditioning, internet access, and pet-friendly accommodation.
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