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Chesterfield, VA vacation rentals
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Best Vacation rentals and Airbnb offers in Chesterfield, VA

Best family friendly Chesterfield, VA vacation rentals

Among the 4 accommodations in Chesterfield, VA, here are the 4 best family friendly rentals

Extended Stay· Private Yard· Near Richmond.7guests - Chesterfield, VA
10 30 reviews

Extended Stay· Private Yard· Near Richmond.7guests

apartment, Bensley
This family-friendly Richmond house rental in Bensley offers easy access to I-95, placing you near Downtown Richmond, VCU, Maymont Park, Kings Dominion, and Busch Gardens.
The three-bedroom, two-bathroom home comfortably sleeps seven guests and features a fully equipped kitchen, laundry facilities, a spacious fenced backyard with a hammock and trampoline, and free on-site parking; pet-friendly (additional fee applies).
The Painted Jungle Near Downtown Rva Free Parking - Chesterfield, VA
10 2 reviews

The Painted Jungle Near Downtown Rva Free Parking

house, Bensley
This guest house in Bensley is located 9 miles, a 13-minute drive, from Downtown Richmond and is a 5-minute walk from a bakery and restaurant, with SwimRVA less than 5 minutes away and Carytown, Scott's Addition, VCU, Maymont, and VMFA a short drive.
This 2-bedroom, 1-bathroom rental accommodates up to 5 guests and features a kitchenette with an induction cooktop, microwave, and full-size fridge, free private driveway parking, keyless self-check-in, an in-unit washer/dryer, fast WiFi, and a fenced backyard, making it family and pet-friendly.
New Modern Unit In Historic Old Manchester. - Chesterfield, VA
9.9 299 reviews

New Modern Unit In Historic Old Manchester.

apartment, Richmond
This family-friendly apartment is located in Richmond, just a mile from Belle Isle and two miles from Virginia Commonwealth University. The apartment has excellent ratings for location, cleanliness, and user experience.
The apartment has two bedrooms and two bathrooms, comfortably accommodating four guests. It includes a fully equipped kitchen, a terrace, a garden, and parking, making it a perfect choice for families and groups.
Stonewall Manor  Cozy 1-bedroom With Wifi And Ac On Five Star Horse Farm. - Chesterfield, VA
10 6 reviews

Stonewall Manor Cozy 1-bedroom With Wifi And Ac On Five Star Horse Farm.

apartment, Brandermill
This Brandermill apartment rental offers a peaceful retreat near Pocahontas State Park and other Chesterfield attractions, providing easy access to outdoor recreation and sporting events like those at Southside Speedway. This one-bedroom, one-bathroom unit sleeps four guests comfortably, featuring a full kitchen with a refrigerator and microwave, Wi-Fi, air conditioning, a queen-size bed, and an optional air mattress; enjoy self-catering and convenient amenities.

Best pet friendly Chesterfield, VA vacation rentals

Among the 4 accommodations in Chesterfield, VA, here are the 4 best pet friendly rentals

Natures Passage - 2bd/2ba - Chesterfield, VA
No reviews

Natures Passage - 2bd/2ba

apartment, Richmond
This 2-bedroom, 2-bathroom apartment in Richmond's Maury neighborhood offers a unique urban oasis within a historic tobacco factory, located within 0.5 miles of the American Civil War Center at Historic Tredegar and the Edgar Allan Poe Museum.
This 1210 square foot residence accommodates up to 4 guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace/balcony, garden access, a tennis court, and parking, with premium amenities including a rooftop lounge, pool, fitness center, and rock climbing wall.
Near Hospitals & Attractions: Richmond Getaway! - Chesterfield, VA
No reviews

Near Hospitals & Attractions: Richmond Getaway!

apartment, Bensley
This pet-friendly apartment in Bensley, Richmond, is situated 10 miles from the Altria Theater and Virginia Holocaust Museum, offering a local feel with convenient access to downtown dining and Virginia Beach, and is within 24 miles of the Metro Richmond Zoo and Richmond International Airport.
This 1500 square foot single-story home accommodates up to 6 guests with 3 bedrooms, 2 bathrooms, a full kitchen, yard space with outdoor seating, a grill, and 2 Smart TVs, plus a fireplace for cozy evenings.
Luxury Bailey Mountain - Chesterfield, VA
9.6 10 reviews

Luxury Bailey Mountain

apartment, Brandermill
This Brandermill house rental is conveniently located near Hull Street Road, within walking distance of a Wawa and a short drive from shopping centers like Walmart, BJ's, Food Lion, and Kroger.
This four-bedroom, two-bathroom home sleeps eight guests and features a fully equipped kitchen, in-unit laundry, a living room with a smart TV, and a backyard; nearby Route 288 provides easy access to other areas of Richmond.
The Birdhouse - Cozy Cottage Retreat In Richmond - Chesterfield, VA
10 3 reviews

The Birdhouse - Cozy Cottage Retreat In Richmond

cottage, Richmond
This garden cottage is located in Richmond's historic Swansboro neighborhood, offering a quiet retreat just minutes from downtown attractions including the American Civil War Center at Historic Tredegar and the Federal Reserve Bank of Richmond Money Museum.
This accommodation accommodates up to 3 guests in 1 bedroom and features a full kitchen, air conditioning, a private fenced yard, and off-street parking, with pets allowed.

Frequently Asked Questions about vacation rentals in Chesterfield, VA

  • What are the must-see sights in Chesterfield County, Virginia?

    For must-see sights in Chesterfield County, Virginia, you've got some great options. The Chesterfield County Fairgrounds hosts numerous events throughout the year. History buffs will love the historic Manchester area, with its charming architecture and the Canal Walk. You can also explore the expansive and beautiful Dutch Gap Conservation Area.
  • What are the best Airbnb and vacation rentals in Chesterfield, VA?

    Private Guest Apt On Creek W/ Patio & Fire Feature, Gorgeous Creek View From Your Private Eyrie and The Black Pot - Free Parking are the most popular Airbnb and vacation rentals in Chesterfield, VA among travelers.

  • Are there unique natural phenomena in Chesterfield County, Virginia?

    While Chesterfield County doesn't have dramatic, singular natural phenomena like geysers, its natural beauty lies in its varied landscapes. The James River provides scenic views and opportunities for water activities. The forests and parks offer hiking and wildlife viewing. Dutch Gap, a man-made waterway, is a unique feature resulting from Civil War-era fortifications.
  • What are the most popular Airbnbs in Chesterfield, VA?

  • What essentials should you bring along for a trip to Chesterfield County, Virginia?

    Packing for Chesterfield depends on the time of year. Comfortable walking shoes are a must, as is sunscreen and insect repellent, especially during warmer months. Don't forget a hat and sunglasses for sun protection. Check the weather forecast before you go and pack accordingly; layers are always a good idea.
  • What are the best vacation rentals with a pool in Chesterfield, VA?

  • What famous events or festivals are happening in Chesterfield County, Virginia?

    Chesterfield County hosts many local events throughout the year. The Chesterfield County Fair is a major annual event, attracting many visitors. Check local listings for specific dates and details on other smaller community festivals and events.
  • What are the best rentals for families and kids in Chesterfield, VA?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Chesterfield County, Virginia?

    A daily budget in Chesterfield County can vary greatly depending on your preferences. For a modest budget, you could plan for around $100-$150 per day, covering budget-friendly accommodations, meals, and some activities. A higher budget could easily reach $300 or more per day, allowing for more luxurious options.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesterfield, VA?

    The best vacation rentals or Airbnb with a jacuzzi in Chesterfield, VA are The Branson Lakeside Villa, Chester Virginia Fully Furnished Apt and Extended Stay Home~insurance+military Stay Welcome.

  • Where can you find the best restaurants serving local dishes in Chesterfield County, Virginia, and what are the must-try specialties?

    Chesterfield has a diverse culinary scene. While there aren't specific 'local' dishes unique only to Chesterfield, you'll find excellent Southern comfort food. Many restaurants in the Manchester area offer traditional Southern fare. Exploring different restaurants in the county will reveal a variety of cuisines and options.
  • What are some less-famous attractions in Chesterfield County, Virginia, that are worth the visit?

    Beyond the well-known spots, consider exploring some of Chesterfield's smaller parks and nature trails. The various neighborhood parks offer quiet escapes and opportunities for a peaceful stroll. Look into local historical markers and smaller museums for a glimpse into the county's rich history.
  • What are the best activities for engaging with locals and understanding their culture in Chesterfield County, Virginia?

    Attending local events like farmers' markets or community festivals is a great way to interact with locals. Striking up conversations with people at these events can offer insights into the community. Visiting local businesses, such as independent shops and restaurants, can also provide a more authentic experience.
  • What unique natural landscapes and terrain features can travelers explore in Chesterfield County, Virginia?

    Chesterfield County offers a blend of natural landscapes. The James River provides waterfront access and views. The county also has several parks and forests with hiking trails, offering opportunities to explore wooded areas and experience the natural beauty of the region. Dutch Gap is a unique man-made feature worth exploring.
  • How many days are ideal for visiting Chesterfield County, Virginia, and what are some itinerary suggestions?

    A long weekend (3-4 days) is a good amount of time to explore Chesterfield County. You could spend a day exploring the Manchester historic district, another at Dutch Gap Conservation Area, and a third visiting local parks and restaurants. Adjust this based on your interests and pace.

Nearby regions

Best Chesterfield, VA vacation rentals with a pool

Among the 3 accommodations in Chesterfield, VA, here are the 3 best rentals with a pool

Landing | Modern 3bd, Pool, Courtyard - Chesterfield, VA
No reviews

Landing | Modern 3bd, Pool, Courtyard

apartment, Richmond
This Richmond apartment is situated in the historic Old Town Manchester district, offering a 12-minute walk to the James River and a 3-minute drive to Broad Street.
This 1270 sq ft residence features 3 bedrooms, 3 bathrooms, and accommodates up to 6 guests with amenities including air conditioning, Wi-Fi, a refrigerator, and a washing machine.
Root & Bloom - 2bd/2ba - Chesterfield, VA
No reviews

Root & Bloom - 2bd/2ba

apartment, Richmond
This 2-bedroom, 2-bathroom downtown Richmond condo offers convenient access to Broad Street, located 2.1 miles away, and the James River, 1.3 miles away, placing you near Capitol Square and Libby Hill Park.
This pet-friendly apartment features a fully equipped kitchen, air conditioning, Wi-Fi, on-site parking, a swimming pool, garden, and a terrace with a fire pit, accommodating up to 4 guests with a 10:00 AM check-out.
Charming 2-bedroom Vintage Modern Condo In Midlothian With Ac, Wi-fi, Pool - Chesterfield, VA
10 1 review

Charming 2-bedroom Vintage Modern Condo In Midlothian With Ac, Wi-fi, Pool

apartment, Bon Air
This two-bedroom, two-bathroom condo in North Chesterfield, a neighborhood of Midlothian, offers convenient access to shopping at Broad Street and Short Pump Town Center, and entertainment at Richmond Raceway and the Riverfront's Allianz Amphitheater.
The 2-bedroom unit features a king and queen bed, sleeps four, includes a microwave, dishwasher, washer/dryer, Wi-Fi, and an enclosed patio, providing a comfortable stay near Bon Air.

Best Chesterfield, VA vacation rentals with parking

Cozy Chesterfield 3 Bedroom - Chesterfield, VA
9.5 33 reviews

Cozy Chesterfield 3 Bedroom

apartment, Richmond
This Richmond rental is located in a stylish and calm neighborhood, close to the city's major attractions. It has received very good ratings for user experience, location, and cleanliness.
The apartment has three bedrooms and one bathroom, comfortably accommodating six guests. It comes with amenities like air conditioning, parking, internet, and a kitchen equipped with a fridge.
Extended Stay America Suites - Colonial Heights - Fort Lee - Chesterfield, VA
8.4 100 reviews

Extended Stay America Suites - Colonial Heights - Fort Lee

fort, Colonial Heights
Extended Stay America Suites Colonial Heights Fort Lee is located in Colonial Heights, within a 15-minute walk of the Appomattox River and Southpark Mall, and 1.1 miles from Swaders Sports Park.
This extended stay hotel offers complimentary Wi-Fi, on-site picnic areas, vending machines, laundry facilities, and rooms with kitchenettes featuring full-size refrigerators and stovetops.
Your Futura Stay: 4 Br Near Ric With Gaming Lounge - Chesterfield, VA
No reviews

Your Futura Stay: 4 Br Near Ric With Gaming Lounge

apartment, Montrose
This pet-friendly vacation home is located in Richmond's Montrose district, offering proximity to recreational parks and the James River, with Broad Street just a 4-minute drive away.
This spacious 1720 sq ft house accommodates up to 8 guests with 4 bedrooms, 1 bathroom, a full kitchen, air conditioning, a terrace, a garden, and parking, plus Wi-Fi and spa access.
Charming 1-bedroom Suite With Wifi And Ac In Bon Air - Chesterfield, VA
10 8 reviews

Charming 1-bedroom Suite With Wifi And Ac In Bon Air

apartment, Bon Air
This Bon Air apartment rental in Richmond, Virginia offers convenient access to Broad Street and Short Pump Town Center, with nearby hiking/biking trails and wineries.
The 880-square-foot unit features one bedroom, one bathroom, sleeps seven, and includes amenities such as WiFi, air conditioning, a spa, and parking.
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