Best apartment offers in Chesapeake, VA

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Chesapeake, VA apartments
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790 Holiday apartments in Chesapeake, VA

Holiday Apartments in the CBD of in Chesapeake, VA

Stay exactly where the nightlife, cafes, and historic streets meet at city centre apartments in Chesapeake, VA.

Premium Comfort Home - Chesapeake, VA
8.8 22 reviews

Premium Comfort Home

apartment, Chesapeake
This two-bedroom flat is located in a quiet, residential district of Chesapeake, offering a peaceful retreat approximately 8 kilometres from the Chesapeake City Hall and the Great Bridge Battlefield and Waterways Museum.
This apartment accommodates up to six guests and features a kitchen with a dishwasher, air conditioning, and parking, providing a comfortable base for exploring local amenities and attractions within a 5-kilometre radius.
The Cozy Cottage Two Bedroom, King Bed House - Chesapeake, VA
9.9 133 reviews

The Cozy Cottage Two Bedroom, King Bed House

apartment, Chesapeake
This charming Cape Cod style house is located in a central area of Chesapeake, within easy reach of local attractions and landmarks. The property has received excellent ratings for cleanliness, location and user experience.
The house has two bedrooms, one bathroom and can accommodate up to four guests. It is equipped with modern amenities including air conditioning, a fully equipped kitchen and smart TVs in every room.
Entire Apartment In Chesapeake, Virginia - Chesapeake, VA
9.8 11 reviews

Entire Apartment In Chesapeake, Virginia

apartment, Chesapeake
This centrally located flat in Chesapeake offers excellent access to Hampton Roads attractions, being just a 2-minute drive from the I64 motorway, placing it minutes from the Oceanfront and Downtown Norfolk.
This spacious, pet-friendly apartment with high ceilings accommodates up to four guests, featuring two bathrooms, a fully equipped kitchen with a Keurig and rice cooker, a Smart TV with Netflix, a private balcony, and optional weekly cleaning for longer stays.
Simply Amazing In Chesapeake - Chesapeake, VA
9.9 38 reviews

Simply Amazing In Chesapeake

apartment, Chesapeake
This Chesapeake property is conveniently located just 5-10 kilometres from Greenbrier Mall, various shopping plazas, and restaurants, making it a great base for exploring the area. It also enjoys a prime position, being only 15 kilometres from the Virginia Beach oceanfront and 10 kilometres from Ocean View in Norfolk. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
This spacious home offers three bedrooms and two bathrooms, comfortably accommodating up to eight guests. The fully equipped kitchen features a fridge, freezer, microwave, and dishwasher, alongside a garden, parking, air conditioning, and internet access, ensuring a comfortable and enjoyable stay.

Best family friendly Chesapeake, VA Holiday Apartments

Among the 790 accommodations in Chesapeake, VA, here are the 4 best family friendly holiday apartments

Park View Place - Apt 1 - Historic Olde Towne - Chesapeake, VA
8.6 39 reviews

Park View Place - Apt 1 - Historic Olde Towne

apartment, Portsmouth
This charming apartment is located in Olde Towne Portsmouth, a historic district just next to Red Lion Park, offering a peaceful retreat within walking distance of the city's attractions. The property enjoys excellent ratings for location, cleanliness, and overall user experience.
The apartment can accommodate up to 3 guests and features a comfortable living space with modern amenities like a smart TV, high-speed Wi-Fi, and a well-equipped kitchen. Guests can enjoy the convenience of air conditioning, parking, and access to a shared common space, making this a perfect choice for families or groups seeking a comfortable and convenient stay in Portsmouth.
Whispering Woods Estate- Secluded And Spacious - Chesapeake, VA
9.9 31 reviews

Whispering Woods Estate- Secluded And Spacious

apartment, Virginia Beach
This three-storey house is situated in a rural area of Virginia Beach, just 4 km from the Sportsplex, PAAC, and the Amphitheatre, and within easy reach of beaches, shops, restaurants, and breweries. It has received excellent ratings for location, cleanliness, and user experience.
The property sleeps up to 15 guests and is well-equipped with a spacious living room, large kitchen, multiple dining areas, and a screened-in porch. Guests can enjoy swimming in the pool, fishing in the ponds, relaxing in the gardens, or simply enjoying the peaceful atmosphere.
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.
Lighthouse Launch - Spacious 4 Br/2ba Retreat - Chesapeake, VA
9.5 51 reviews

Lighthouse Launch - Spacious 4 Br/2ba Retreat

apartment, Portsmouth
This four-bedroom, two-bathroom house in a quiet Portsmouth neighbourhood is a short drive (approx. 5km) from Portsmouth's waterfront and around 48km from Virginia Beach.
This self-catering property sleeps eight, boasting a fully equipped kitchen, high-speed Wi-Fi, a Smart TV, and a washer/dryer, alongside exterior security cameras and a decibel monitor for a peaceful stay.

Frequently asked questions about apartment rentals in Chesapeake, VA

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

    The Chesapeake Historical Society Museum is a great place to learn about the city's rich history. The South Norfolk Jordan Branch Railroad Museum is another great option, with a collection of historic locomotives and rolling stock. The Chesapeake Bay Maritime Museum in nearby St. Michaels, Maryland is also worth a visit. It's a bit of a drive, but it's a great place to learn about the history of the Chesapeake Bay.
  • 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 number of parks and green spaces, making it a great place to enjoy the outdoors. The city is also home to a 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.

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

    The Chesapeake Farmers Market is a great place to find fresh produce, local crafts, and delicious food. It's held every Saturday from May to October at the Chesapeake City Park. There are also several food trucks that can be found around the city, particularly in the Greenbrier area.
  • 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 has a public bus system, Hampton Roads Transit, which operates throughout the city and connects to other cities in the Hampton Roads area. It's not as extensive as the system in a larger city, but it can be a convenient and affordable way to get around. If you're planning on exploring the city, it's best to rent a car.
  • 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 held every October. The Chesapeake Arts Festival is another highlight, featuring local artists and musicians. The Chesapeake Bay Seafood Festival is a great way to sample fresh seafood and enjoy live music.
  • What are the best pet friendly apartments in Chesapeake, VA?

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

    Most apartments in Chesapeake include central air conditioning, a refrigerator, stove, and oven. Some apartments also have a dishwasher, washer, and dryer. The availability of these amenities will vary depending on the specific apartment complex.
  • What are the best apartments with parking in Chesapeake, VA?

Popular destinations

Discover Apartments with Balconies in Chesapeake, VA

Sip your morning coffee while taking in the local neighborhood views from apartments with balconies in Chesapeake, VA.

Spacious Modern 3-bedroom House In Beautiful Portsmouth City. - Chesapeake, VA
8.0 1 review

Spacious Modern 3-bedroom House In Beautiful Portsmouth City.

apartment, Portsmouth
This four-bedroom, three-bathroom flat in Portsmouth is conveniently located 5.6 kilometres from Town Point Park and 16.1 kilometres from Chesapeake Bay, with the Children's Museum of Virginia and Portsmouth Naval Shipyard Museum a mere 2.4 kilometres away.
Guests can enjoy complimentary Wi-Fi, air conditioning, and on-site laundry facilities in this accommodation, which also features a sunroom or lanai and offers parking for up to six people.
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.
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.
Beach Family Time Enjoy The Backyard Pool And Sunroom - Chesapeake, VA
8.6 37 reviews

Beach Family Time Enjoy The Backyard Pool And Sunroom

apartment, Virginia Beach
This three-bedroom apartment in Virginia Beach is conveniently located just minutes from the beach and waterways, with easy access to Interstate 64. It has received very good ratings from previous guests and is ideal for families and groups.
The 260 square metre apartment comfortably sleeps up to 10 guests and comes with a range of amenities including a private pool, sunroom, top-deck bath, and a garden. Guests can enjoy activities such as jet skiing, kayaking, cave exploring, and mountain biking, as well as exploring the nearby cultural attractions and family-friendly activities.

Best Chesapeake, VA holiday apartments with parking

Stylish | Cozy Home Near Downtown Norfolk - Chesapeake, VA
9.1 56 reviews

Stylish | Cozy Home Near Downtown Norfolk

apartment, Norfolk
This mid-century modern flat is located in a residential area, just 8km from downtown Norfolk and 20-30km from the beaches of Ocean View and Virginia Beach. The property has received excellent ratings for cleanliness and location, and guests have described it as a "very good" stay.
The flat is fully furnished and equipped, with a well-stocked kitchen and a workspace in the living room, making it ideal for families or groups of up to 4. Amenities include a private garden, parking, air conditioning, and internet access, as well as a pet-friendly policy for service dogs.
Cavalier Manor: Pool, Luxury Home, & Scenic Views - Chesapeake, VA
9.7 75 reviews

Cavalier Manor: Pool, Luxury Home, & Scenic Views

apartment, Portsmouth
This five-bedroom apartment is situated in Cavalier Manor on Crystal Lake, a short drive from Portsmouth's historic downtown and waterfront. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The apartment comfortably accommodates up to 14 guests, offering plenty of space for families or groups of friends. It boasts a private pool and hot tub, an outdoor kitchen, fireplaces, and stunning water views, making it the perfect place to relax and enjoy the beautiful surroundings.
Portsmouth 3br Near Casino, Comfy, Spacious Yard Stay, Sleeps 6! - Chesapeake, VA
9.2 17 reviews

Portsmouth 3br Near Casino, Comfy, Spacious Yard Stay, Sleeps 6!

apartment, Portsmouth
This Portsmouth holiday home is situated within 3km of the Commodore Theatre, Virginia Sports Hall of Fame and Museum, and Children's Museum of Virginia, and within 5km of the Portsmouth Naval Shipyard Museum.
The 130 square metre property boasts three bedrooms sleeping six, two bathrooms, a fully equipped kitchen, a jacuzzi, a terrace, a garden, parking, and free Wi-Fi; nearby attractions include the Tidewater Yacht Marina.
Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth - Chesapeake, VA
8.4 10 reviews

Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth

apartment, Portsmouth
This one-bedroom flat in Portsmouth is situated a 19-minute drive from Town Point Park and 40 minutes from Chesapeake Bay, offering convenient access to the Chrysler Museum of Art and the Children's Museum of Virginia.
This pet-friendly apartment accommodates up to three guests and includes on-site parking, complimentary Wi-Fi, air conditioning, and essential amenities such as towels, linens, and soap, with a check-out time of 12:00.

Best Chesapeake, VA holiday apartments with air conditioning

The Mayfield - Chesapeake, VA
9.6 18 reviews

The Mayfield

apartment, Portsmouth
Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood. - Chesapeake, VA
No reviews

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

apartment, Chesapeake
"The Ponderosa A" - Close To The Casino & Concerts - Chesapeake, VA
9.8 96 reviews

"The Ponderosa A" - Close To The Casino & Concerts

apartment, Portsmouth
Stylish Two Bdrm, 1 1/2 Bth, King Bed Townhouse - Chesapeake, VA
9.9 61 reviews

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

apartment, Portsmouth

Discover Luxury Holiday Apartments in Chesapeake, VA

Relax in a stylish, high-end urban sanctuary featuring premium finishes at luxury holiday apartments in Chesapeake, VA.

Escape To The Water! - Chesapeake, VA
10 24 reviews

Escape To The Water!

apartment, Portsmouth

Holiday Apartments with a Pool in Chesapeake, VA

Balance remote work or sightseeing with relaxing laps in a refreshing on-site pool at holiday apartments in Chesapeake, VA.

5-bedroom Home In Chesapeake W/ Pool & Gym. Close To Shopping And Restaurants! - Chesapeake, VA
8.0 2 reviews

5-bedroom Home In Chesapeake W/ Pool & Gym. Close To Shopping And Restaurants!

apartment, Chesapeake
Luxury Lakefront Estate & Guest House W/ Pool - Chesapeake, VA
10 8 reviews

Luxury Lakefront Estate & Guest House W/ Pool

apartment, Portsmouth
Condo ∙ 2 Bedrooms ∙ 6 Guests - Chesapeake, VA
No reviews

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Chesapeake
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

Check Out Apartments with a Hot Tub in Chesapeake, VA

Take your self-catering holiday to the next level with a private, bubbling hot tub right on your terrace at holiday apartments in Chesapeake, VA.

The Chesapeake Gray  Historical Waterside District 20 Mins To Oceanfront - Chesapeake, VA
9.4 8 reviews

The Chesapeake Gray Historical Waterside District 20 Mins To Oceanfront

apartment, Norfolk
Condo ∙ 1 Bedroom ∙ 6 Guests - Chesapeake, VA
No reviews

Condo ∙ 1 Bedroom ∙ 6 Guests

apartment, Chesapeake
Wooded Wonderland - Chesapeake, VA
9.6 15 reviews

Wooded Wonderland

apartment, Portsmouth
Condo ∙ 1 Bedroom ∙ 4 Guests - Chesapeake, VA
No reviews

Condo ∙ 1 Bedroom ∙ 4 Guests

apartment, Chesapeake
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