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

Harbor Haven Retreat - Chesapeake, VA
9.6 18 reviews

Harbor Haven Retreat

apartment, Portsmouth
This spacious Portsmouth, Virginia house is centrally located in the historic downtown area, within walking distance of shops and restaurants, and a short drive (distances unspecified) from local beaches and the Portsmouth Casino.
Sleeping up to 15 guests in five bedrooms and three bathrooms, this fully equipped property boasts a kitchen with fridge, microwave, dishwasher and washer/dryer, air conditioning, a garden, parking, and excellent guest reviews.
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.
Spacious Chesapeake Home W/ Pool Table! - Chesapeake, VA
8.4 15 reviews

Spacious Chesapeake Home W/ Pool Table!

apartment, Chesapeake
This 4-bedroom Chesapeake holiday home is situated in Western Branch North, just a short distance from Chesapeake Square Mall and a drive from Portsmouth City Park and the Chesapeake Arboretum. It has received very good ratings from previous guests.
The property offers 223 square metres of space, accommodating up to 8 guests, with 4 bedrooms and 3 bathrooms. It features a range of amenities, including a private yard, a deck, a pool table, a jetted tub, smart TVs, a fireplace, a washer and dryer, and free Wi-Fi.
Trycams Humble Abode - Chesapeake, VA
9.3 51 reviews

Trycams Humble Abode

apartment, Chesapeake
This Chesapeake property is conveniently located just a short drive from Virginia Beach, Busch Gardens, and the Virginia Aquarium, making it ideal for exploring the region's attractions. The accommodation has received excellent ratings for cleanliness and user experience, while its location has been rated very good.
This three-bedroom house can comfortably accommodate up to eight guests, with queen-sized beds in each bedroom and a queen-sized sofa bed downstairs. The house is well-equipped with a full kitchen, including a dishwasher, microwave, and other appliances, as well as a private outdoor space and parking.

Best Chesapeake, VA holiday apartments with a balcony

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.
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.
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.
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

Furnished Townhouse In Downtown Vb - Chesapeake, VA
No reviews

Furnished Townhouse In Downtown Vb

apartment, Virginia Beach
This three-bedroom Virginia Beach townhouse enjoys a central location, minutes from Town Centre, a short drive (approximately 8km) from the Virginia Beach oceanfront, and convenient access to the Naval Base and a hospital.
Sleeping six guests comfortably, the property boasts a fully equipped kitchen, two bedrooms with TVs, queen-sized memory foam mattresses in all bedrooms, and onsite parking for four cars.
Cozy Retreat - Chesapeake, VA
9.6 117 reviews

Cozy Retreat

house, 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.
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 Modern Retreat, Peaceful Stay Near Everything - Chesapeake, VA
9.7 13 reviews

Cozy Modern Retreat, Peaceful Stay Near Everything

apartment, Portsmouth
This new-construction luxury flat in Portsmouth offers proximity to Historic Olde Towne Portsmouth and is a convenient 7-minute drive from the casino, placing it under 8 kilometres from Downtown Norfolk's premier dining and entertainment.
This spacious property accommodates up to 8 guests with 4 bedrooms and 3.5 bathrooms, featuring two master suites, a private backyard, a welcoming front porch, central air/heat, and high-speed WiFi.

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.
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).
Experience Timeless Luxury At Cavalier Manor On A Lake - Chesapeake, VA
9.6 10 reviews

Experience Timeless Luxury At Cavalier Manor On A Lake

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.
Yes Queen! The Bridgerton House - Chesapeake, VA
10 44 reviews

Yes Queen! The Bridgerton House

apartment, Portsmouth
This stunning Queen Anne-style property enjoys a waterfront location on the Elizabeth River in Portsmouth, offering direct shallow water access and proximity to various local attractions (distances to specific landmarks would need to be provided).
This four-bedroom, three-bathroom house sleeps eight guests and boasts a Bridgerton-inspired interior, a wrap-around patio with river views, a fully equipped kitchen including a dishwasher, air conditioning, parking, and a garden.
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