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Best Vacation rentals and Airbnb offers in Chester, VA
9.8 516 reviews
Chester, VA
11/18 – 11/22
$154/nighttotal: $616 (4 )
Warm, Cozy And Comfortable Houseboat, Gated Marina
1 2
boat , Chester
The GiaMaria yacht is docked in a secluded oxbow of the James River, nine miles from Richmond, Virginia, and a short distance from the Richmond National Battlefield Park. The 1-bedroom, 1-bathroom yacht sleeps four guests and offers a fully equipped kitchen, comfortable sleeping quarters, and access to the Lily Pad Cafe, an outdoor restaurant located two miles from the marina.
9.8 64 reviews
Chester, VA
07/02 – 07/05
$346/nighttotal: $1038 (3 )
Cozy Stay - 4br In Petersburg
4 4
apartment , Petersburg
This historic house is located in downtown Petersburg, Virginia, just a 5-minute walk from the city's historic architecture, restaurants, and shops. The 4-bedroom, 3-bathroom home comfortably sleeps 8 guests and features a fully equipped kitchen, private patio, and cozy living spaces, making it ideal for families or groups visiting Petersburg National Battlefield, Pamplin Historical Park, or other nearby attractions.
9.2 51 reviews
Chester, VA
11/18 – 11/22
$281/nighttotal: $1124 (4 )
Recline At Timberline! Family Friendly!
3 2
apartment , Chester
This Colonial Heights vacation home, located 1.9 miles from the Swift Creek Mill Theatre and within 6 miles of Parker's Battery Park and Point of Rocks Park, offers a convenient base for exploring Chester, Virginia. This 1400-square-foot house features three bedrooms, two bathrooms, sleeps six guests, and includes amenities such as a fully equipped kitchen, Wi-Fi, a private fenced yard with a barbecue grill, and air conditioning.
10 16 reviews
Chester, VA
07/02 – 07/05
$526/nighttotal: $1578 (3 )
Glamorous 4br Home, Office & Large Yard Near Ric
4 4
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.
10 20 reviews
Chester, VA
07/02 – 07/05
$338/nighttotal: $1014 (3 )
The Plum Street Double House
1 4
apartment , Petersburg
This historic 234-year-old brick home, listed on the National Registry of Historic Places, is conveniently located two blocks from Virginia State University in a quiet Petersburg neighborhood. This 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features modern amenities such as private covered carport garage, in-unit washer/dryer, and queen-size bedrooms with fireplace heaters, offering a comfortable stay for travelers seeking accommodations near Virginia State University.
9.6 16 reviews
Chester, VA
07/02 – 07/05
$336/nighttotal: $1008 (3 )
Charming 3-bedroom Home In Petersburg, Va
1 4
apartment , Petersburg
This peaceful home is located in a quiet neighborhood, just a short distance from Petersburg's main attractions. The area is perfect for those seeking a relaxing escape from the city center. This comfortable vacation rental has three bedrooms and two bathrooms, comfortably accommodating up to six guests. The home is equipped with a full kitchen, including a fridge, freezer, microwave, and dishwasher, as well as air conditioning, parking, and internet access.
9.9 82 reviews
Chester, VA
11/18 – 11/22
$244/nighttotal: $976 (4 )
Parkside Log Cabin
1 2
cabin , Chester
This 1930s log cabin rental near Richmond, Virginia, is nestled within a rural section of a National Battlefield Park, offering a secluded retreat just 20 minutes from downtown. The one-bedroom, one-bathroom cottage sleeps two guests and features a fully equipped kitchen, air conditioning, a private pond for canoeing and fishing, and a luxurious bathroom with an oversized shower.
Chester, VA
07/02 – 07/05
$318/nighttotal: $954 (3 )
11 Mi To Fort Lee: 30-acre Retreat W/ Scenic Views
2 4
apartment , Matoaca
This Petersburg vacation rental, a fort, is located 2 miles from the city and 4 miles from Lake Chesdin, offering mountain views from its private 30-acre property. This 1500 square foot accommodation accommodates up to 6 guests and features 2 bedrooms, 1 bathroom, a full kitchen, air conditioning, WiFi, a pool table, and direct access to on-site hiking trails, with trailer parking and an EV charger available.
9.7 7 reviews
Chester, VA
11/18 – 11/22
$346/nighttotal: $1384 (4 )
The Divine Cottage: Woodsy Hideaway!
1 2
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.
Chester, VA
07/02 – 07/05
$273/nighttotal: $819 (3 )
Lisa's Ranch
2 4
apartment , Richmond
This Richmond rental condo is located approximately 6 miles from the Museum of Confederacy, University Stadium, and the Greater Richmond Convention Center. This 1000-square-foot apartment accommodates up to 7 guests with 2 bedrooms and 1 bathroom, featuring a fully equipped kitchen, air conditioning, on-site parking, complimentary WiFi, and outdoor seating.
9.2 46 reviews
Chester, VA
07/02 – 07/05
$152/nighttotal: $456 (3 )
Civil Century 2 Bedroom “B” Suite!
1 4
apartment , Petersburg
This 1875 Victorian home, located in Petersburg, Virginia's Folly Castle historic district, is two minutes from downtown and five minutes from I-95. The two-bedroom, one-bathroom house sleeps four, features original pine floors, a private upstairs retreat with kitchenette, two Smart TVs, and is near antique shops and diners.
10 8 reviews
Chester, VA
07/02 – 07/05
$387/nighttotal: $1161 (3 )
Charming 1-bedroom Suite With Wifi And Ac In Bon Air
1 4
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.
Discover Family-Friendly Vacation Rentals in Chester, VA
The right family vacation rental in Chester, VA makes all the difference, keeping you close to top city attractions.
9.6 87 reviews
Chester, VA
11/18 – 11/22
$246/nighttotal: $984 (4 )
Recline At Timberline, Family Friendly!
1 2
apartment , Chester
This tri-level apartment is located between Colonial Heights and Chester, just a short drive from Interstate 95 and the SouthPark mall. The property has consistently received excellent reviews for its cleanliness, location, and overall user experience. The apartment offers three bedrooms and one bathroom, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a private backyard with a playset, a screened-in porch, and entertainment options like streaming services and multiple TVs.
9.6 9 reviews
Chester, VA
07/25 – 07/27
$398/nighttotal: $796 (2 )
Charming Retreat W/ Pool Table In Chesterfield!
3 3
apartment , Chester
This Chesterfield, Virginia apartment rental is located in a quiet neighborhood, a short drive from both downtown Richmond and Mechanicsville, offering easy access to major highways and attractions like Iron Bridge Sports Park and Pocahontas State Park. This 1,560-square-foot, three-bedroom, two-bathroom home features a spacious split-level layout with multiple living areas, a pool table, a large deck, and can comfortably accommodate up to eight guests, also including laundry facilities and a fully equipped kitchen.
8.0 1 review
Chester, VA
07/02 – 07/05
$260/nighttotal: $780 (3 )
Prime Location 2 Br Oasis With Washer And Dryer
2 4
apartment , Manchester
This Spring Grove apartment rental is conveniently located 8-11 miles from Richmond attractions such as the University of Richmond Stadium, the Greater Richmond Convention Center, and the Virginia Commonwealth University School of the Arts. This 1120-square-foot, two-bedroom, one-bathroom unit sleeps seven and features a fully equipped kitchen with a dishwasher, air conditioning, free Wi-Fi, and free private parking.
8.2 9 reviews
Chester, VA
07/02 – 07/05
$780/nighttotal: $2340 (3 )
Karters Colonial
1 4
apartment , Rockwood
This four-bedroom colonial house rental in North Chesterfield, near Rockwood, offers convenient access to local bars, restaurants, and shopping malls. The 8-guest home features a fully equipped kitchen, in-house laundry, a furnished garage with styling station, private deck with grill, and WiFi/cable TV; a master bedroom and nursery are among its amenities.
Best Chester, VA vacation rentals with parking
Chester, VA
07/02 – 07/05
$437/nighttotal: $1311 (3 )
Classic Colonial Home W/ Private Yard In Richmond!
4 4
apartment , Meadowbrook
This Meadowbrook apartment is located approximately 18 minutes by car from the Greater Richmond Convention Center and Broad Street. This 1930 sq ft rental offers 4 bedrooms, 2 bathrooms, and can accommodate up to 5 guests, featuring a private garden, air conditioning, and on-site laundry.
10 2 reviews
Chester, VA
11/18 – 11/22
$364/nighttotal: $1456 (4 )
The Divine Cottage! Woodsy Hideaway!
3 2
house , Meadowbrook
This secluded, woodsy house in Meadowbrook is located 9.4 to 11 miles from Richmond attractions such as the United States Federal Reserve Money Museum and Richmond International Airport. This 1450 square foot dwelling offers 3 bedrooms, 1 bathroom, and accommodates up to 19 guests, featuring a fully equipped kitchen, air conditioning, free private parking, complimentary Wifi, a pool table, and an outdoor dining area with barbecue facilities.
9.6 8 reviews
Chester, VA
07/02 – 07/05
$258/nighttotal: $774 (3 )
* Prime Location: 2-br Oasis With Washer & Dryer *
2 4
apartment , Manchester
This 2-bedroom apartment is located in North Chesterfield, a short 15-minute drive from Broad Street and 16 minutes from the Greater Richmond Convention Center. The surrounding area offers a peaceful atmosphere with easy access to parks and cultural attractions. This Manchester rental comfortably sleeps 4 guests and features a fully equipped kitchen, a washer and dryer, Wi-Fi, a TV, a garden, a balcony, and parking. Enjoy the convenience of being close to parks, museums, and family-friendly activities.
This Bellwood cabin, located one mile from the James River and 1.3 miles from the Richmond National Battlefield Park, offers easy access to both natural beauty and historical sites. This three-bedroom, two-bathroom vacation home sleeps six and features a fully equipped kitchen with a refrigerator and oven, in-cabin laundry, a TV, and a terrace; charcoal grills and nearby Dorey Park provide additional outdoor options.
Frequently Asked Questions about vacation rentals in Chester, VA
What are the top family-friendly attractions in Chester, VA?
The Chesterfield County Fairgrounds hosts events throughout the year, including the annual Chesterfield County Fair. The nearby Meadowbrook High School also has a nice outdoor track and soccer fields.
What are the best Airbnb and vacation rentals in Chester, VA?
When is the best time to book a vacation rental in Chester, VA?
The best time to book a vacation rental is probably during the spring or fall, when the weather is mild and there are fewer crowds. You might also want to consider booking in advance for major events like the Chesterfield County Fair.
What events or festivals should visitors check out in and around Chester, VA?
The Chesterfield County Fair is a big event in August, and there's also the annual Swift Creek Reservoir Festival in September. The Chesterfield County Museum often hosts events and exhibits throughout the year.
What are the best vacation rentals with a pool in Chester, VA?
What are the best budget-friendly activities in Chester, VA?
You can take a walk or bike ride along the Swift Creek Reservoir, which is free and offers beautiful views. The Chesterfield County Library is also a great place to spend a few hours, and it's completely free.
What are the best rentals for families and kids in Chester, VA?
What are the best restaurants with local dishes in Chester, VA?
There are a few good barbecue restaurants in Chester, like The Pit Stop BBQ and The Smokehouse. For a more casual dining experience, try the Chester Diner, which has been a local favorite for years.
What are the best rentals or Airbnbs with a jacuzzi in Chester, VA?
Are there pet-friendly attractions in Chester, VA?
The Chesterfield County Fairgrounds is pet-friendly, and there are also some dog parks in the area, like the one at the Chesterfield County Library.
What are the benefits of choosing a vacation rental in Chester, VA?
Vacation rentals offer more space and privacy than a hotel, and they can be a great option for families or groups of friends. You can also often find vacation rentals with amenities that are not available in hotels, like a kitchen or laundry facilities.
What are the top sports attractions and facilities in Chester, VA?
The Meadowbrook High School has a nice outdoor track and soccer fields. The Chesterfield County Fairgrounds also hosts a variety of sporting events throughout the year.
Destinations nearby
Top Vacation Rentals with Balconies in Chester, VA
Start your morning right with a vacation rental in Chester, VA featuring a private balcony and stunning views.
Chester, VA
07/02 – 07/05
$524/nighttotal: $1572 (3 )
Inviting New 3br Retreat | Between Two Ponds
3 4
apartment , Hopewell
This newly renovated 3-bedroom, 2-bath rental home is located in Prince George, Virginia, just 3 miles from Ft. Gregg-Adams and near local landmarks like the Beacon Theatre and Weston Manor. This dog-friendly residence accommodates up to 7 guests with modern amenities including a full kitchen, air conditioning, and two Smart TVs, set on a private property with a garden and terrace, offering convenient access to the Dutch Gap Conservation Area.
9.7 394 reviews
Chester, VA
11/18 – 11/22
$172/nighttotal: $688 (4 )
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
1 2
houseboat , Chester
This houseboat is located on the James River in Richmond, just a short distance from Chester, offering a tranquil escape with easy access to nature and history. It has received excellent ratings for cleanliness, location, and user experience. The 400 square foot boat features one bedroom and a fully equipped kitchen with a fridge, freezer, and microwave. Guests can enjoy a garden, a terrace, and a spa, along with a fitness center and parking.
10 2 reviews
Chester, VA
11/18 – 11/22
$613/nighttotal: $2452 (4 )
5-star Comfort, 16 Minutes From Richmond Downtown
3 2
apartment , Meadowbrook
This Meadowbrook apartment rental is conveniently located near Pocahontas State Park and Iron Bridge Sports Park, offering easy access to local attractions like The Lazy Daisy and Uptown Alley. This 1600-square-foot, three-bedroom, three-bathroom dwelling boasts a private balcony, in-unit garage, laundry, and a master suite with a remote-controlled reclining bed, comfortably accommodating up to nine guests.
10 1 review
Chester, VA
07/02 – 07/05
$242/nighttotal: $726 (3 )
Your Private 2-bedroom Sanctuary
1 4
apartment , Richmond
This private, fully furnished first-floor apartment is located in Richmond's McGuire neighborhood, offering proximity to attractions like the American Civil War Center at Historic Tredegar and the Edgar Allan Poe Museum, as well as shopping on Broad Street and Monument Avenue. This 10,620 square foot residence features two private bedrooms, a private kitchen, and a private living room, accommodating up to four guests with amenities including Wi-Fi, air conditioning, and parking.
Neighborhoods and points of interest in Chester, VA
Find the Best Dog-Friendly Vacation Rentals in Chester, VA
Experience a pet-friendly stay in Chester, VA with vacation rentals located steps away from city dog parks and walking trails.
10 2 reviews
Chester, VA
11/18 – 11/22
$393/nighttotal: $1572 (4 )
The Divine Cottage: Woodsy Hideaway!
3 2
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.
9.4 252 reviews
Chester, VA
11/18 – 11/22
$172/nighttotal: $688 (4 )
A Warm And Cozy 50' Houseboat In Gated, Quaint And Peaceful Marina Near The City
1 2
houseboat , Bellwood
This houseboat is located on the James River in Richmond, just a short distance from Richmond National Battlefield Park and Dorey Park, offering a unique waterfront experience. It has received excellent user ratings, making it a popular choice for travelers. This floating home boasts one bedroom and one bathroom, with a total floor area of 360 square feet, comfortably accommodating up to four guests. You'll enjoy a fully equipped kitchen, air conditioning, a terrace, and free parking, along with free Wi-Fi access in public areas.
Chester, VA
06/23 – 06/25
$350/nighttotal: $700 (2 )
Near Hospitals & Attractions: Richmond Getaway!
3 2
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.
9.8 56 reviews
Chester, VA
06/23 – 06/25
$275/nighttotal: $550 (2 )
Spacious Home Near Downtown Rva
1 2
apartment , Meadowbrook
This Meadowbrook vacation rental is conveniently located within walking distance of a park and soccer fields, offering easy access to outdoor activities and a tranquil setting. Guests consistently rate the property highly for its cleanliness, location, and overall experience. The spacious home features three bedrooms and two bathrooms, comfortably accommodating up to seven guests. Amenities include a fully equipped kitchen, air conditioning, a fitness center, and a fenced-in backyard perfect for pets.
