Search vacation rentals in Chesterfield, VA from 100+ sites!

12 available vacation rental offers

-
7
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Chesterfield, VA vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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

Urban Richmond Retreat W/ Rooftop, Hot Tub & Sauna - Chesterfield, VA
No reviews

Urban Richmond Retreat W/ Rooftop, Hot Tub & Sauna

apartment, Richmond
This four-bedroom, two-bathroom apartment is centrally located in Richmond, offering proximity to Capitol Square and Libby Hill Park, with the Science Museum of Virginia and Children's Museum of Richmond within easy reach.
This family-friendly residence features a fully equipped kitchen, air conditioning, a jacuzzi, a terrace, a garden, on-site sauna, and parking, making it ideal for those seeking a comfortable stay with convenient access to local attractions.
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.
The Underground Lounge: A Private Escape - Chesterfield, VA
9.0 2 reviews

The Underground Lounge: A Private Escape

apartment, Richmond
This dog-friendly studio apartment in Richmond's Fan District offers easy walking access to restaurants like Zombie Pizza and WPA Bakery, as well as Carytown and Maymont Park.
The 890-square-foot unit features a queen bed with a trundle, a full-size bed in a semi-private nook, a spa-like bathroom, a private patio, and a fully equipped kitchen; it comfortably sleeps four guests and is close to hiking and biking trails in Forest Hill Park and James River Park System.
Cozy Litle House In Richmond - Chesterfield, VA
8.0 6 reviews

Cozy Litle House In Richmond

apartment, Richmond
This Bellemeade, Richmond vacation rental is conveniently located near the Virginia War Memorial and Canal Walk, with easy access to Broad Street and Monument Avenue.
This three-bedroom, two-bathroom house sleeps six, offering a fully equipped kitchen with a fridge, microwave, and dishwasher, plus amenities like air conditioning, Wi-Fi, and in-unit laundry; nearby attractions include the Science Museum of Virginia and the Children's Museum of Richmond.

Best pet friendly Chesterfield, VA vacation rentals

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

The Divine Cottage: Woodsy Hideaway! - Chesterfield, VA
9.4 14 reviews

The Divine Cottage: Woodsy Hideaway!

apartment, Meadowbrook
This 3-bedroom apartment is situated in the 23234 zip code of Richmond, VA, offering a secluded, wooded retreat approximately 150 yards from the property owners' residence.
This pet-friendly dwelling accommodates up to 8 guests with a fully equipped kitchen, air conditioning, internet, a workspace, a pool table, a charcoal grill, and a brick patio, all accessible via a gravel roadway with a small concrete bridge.
Charming 3-bedroom House With Ac And Wifi In Wonderful Richmond - Chesterfield, VA
8.8 9 reviews

Charming 3-bedroom House With Ac And Wifi In Wonderful Richmond

apartment, Richmond
This Richmond vacation rental is conveniently located near Rockwood Park and Pocahontas State Park, offering easy access to Iron Bridge Sports Park and Richmond Raceway.
The three-bedroom house sleeps six guests comfortably, featuring one king and two queen beds, WiFi, air conditioning, a washer, and is ideal for family vacations or group getaways.
Luxe Cottage - South Chesterfield Stylishly Renovated, W/ Large Master Suite - Chesterfield, VA
9.8 18 reviews

Luxe Cottage - South Chesterfield Stylishly Renovated, W/ Large Master Suite

apartment, Ettrick
Ettrick Cottage offers a unique blend of comfort and convenience in the wooded surroundings of Ettrick. Just 20 minutes south of Richmond, this highly-rated apartment is close to Ettrick Park and Station, South Park Mall, VSU, Fort Gregg-Adams, and Old Towne Petersburg.
The apartment features a spacious layout with three bedrooms, two bathrooms, and a guest capacity of 8. It includes a kitchen, dining area, living room, air conditioning, parking, and internet access. Guests can also enjoy outdoor activities such as motor boating, fishing, mountain biking, and hiking nearby.
Contemporary 3-bedroom Home With Balcony In Rva - Chesterfield, VA
9.6 119 reviews

Contemporary 3-bedroom Home With Balcony In Rva

apartment, Richmond
This 3-bedroom apartment is located in Richmond, just a short drive from the Greater Richmond Convention Center and Museum of Confederacy, with easy access to other attractions like the Virginia Commonwealth University School of the Arts and University Stadium. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This spacious rental offers 1650 square feet of living space, comfortably accommodating up to 6 guests. The apartment includes modern amenities like a fully equipped kitchen, a balcony with quiet street views, and free Wi-Fi, making it perfect for both relaxing and exploring Richmond.

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 1 accommodations in Chesterfield, VA, here are the 1 best rentals with a pool

Aviation Haven: 5 Mins To Ric, Ready For Takeoff! - Chesterfield, VA
10 7 reviews

Aviation Haven: 5 Mins To Ric, Ready For Takeoff!

apartment, Sandston
This Sandston vacation home is conveniently located near Dorey Park (0.8 miles) and within 6 miles of attractions like the Virginia Aviation Museum and Richmond National Battlefield Park.
This 750-square-foot house features two bedrooms, one bathroom, sleeps five, and includes a fully equipped kitchen, in-house laundry, free WiFi, and a backyard.

Best Chesterfield, VA vacation rentals with parking

Colonial Heights Home W/ Large Yard & Bbq Grill! - Chesterfield, VA
No reviews

Colonial Heights Home W/ Large Yard & Bbq Grill!

house, Colonial Heights
This Colonial Heights vacation home is located near Rogers Stadium and Sycamore Rouge Theatre, approximately 22-25 miles from Richmond, VA attractions.
This 1,090-square-foot house features 3 bedrooms, 2 bathrooms, sleeps 11 guests, and includes a fully equipped kitchen, spa, tennis court, and free Wi-Fi.
Charming 1-bedroom Suite With Wifi And Ac In Bon Air - Chesterfield, VA
9.8 9 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.
Glamorous 4br Home, Office & Large Yard Near Ric - Chesterfield, VA
10 20 reviews

Glamorous 4br Home, Office & Large Yard Near Ric

apartment, Meadowbrook
This Chesterfield apartment rental is conveniently located 18 minutes from Richmond International Airport (RIC), providing easy access to Carytown and the Virginia Museum of Fine Arts.
This four-bedroom, 2.5-bathroom Meadowbrook home sleeps eight guests and features a fully equipped kitchen, private patio, large fenced yard, and driveway parking for up to six cars; nearby attractions include the James River Park System.
The Divine Cottage: Woodsy Hideaway! - Chesterfield, VA
10 3 reviews

The Divine Cottage: Woodsy Hideaway!

apartment, Meadowbrook
This 3-bedroom, 1-bathroom rental home in Meadowbrook is located 11 minutes by car from the James River and Pocahontas State Park, offering a rural setting convenient to outdoor recreation and cultural attractions like the American Civil War Center at Historic Tredegar. This pet-friendly residence accommodates up to 10 guests and is a short drive from the Greater Richmond Convention Center, Iron Bridge Sports Park, and family attractions including the Children's Museum of Richmond.