Best Vacation Homes in Chester
House
9.2(49 Reviews)
3 Bedrooms
1 Bath
6 Guests
1400 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
AU $310/Night
7 Nights - AU $2,170
House
9.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1345.49 ft²
- Fireplace/Heating
Parking
Internet
Child Friendly
AU $464/Night
7 Nights - AU $3,248
Hotel
9.8(19 Reviews)
1 Bath
- Fireplace/Heating
Air Conditioner- Child Friendly
Laundry
AU $225/Night
7 Nights - AU $1,578
House
9.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1344 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $369/Night
7 Nights - AU $2,580
House
2 Bedrooms
2 Baths
3 Guests
1603.82 ft²
- Fireplace/Heating
Pool- Parking
- Internet
AU $529/Night
7 Nights - AU $3,704
House
2 Bedrooms
2 Baths
3 Guests
1608 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $493/Night
7 Nights - AU $3,453
House
4 Bedrooms
2 Baths
6 Guests
1270 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $314/Night
7 Nights - AU $2,201
House
2 Bedrooms
3 Baths
6 Guests
Hot Tub- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $304/Night
7 Nights - AU $2,128
Chester Luxury Rentals
Hotel
9.0(87 Reviews)
1 Bath
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
AU $561/Night
7 Nights - AU $3,929
Hotel
9.7(23 Reviews)
4 Baths
Private Pool- Pool
- Pet Friendly
- Internet
AU $331/Night
7 Nights - AU $2,321
House
4 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $302/Night
7 Nights - AU $2,111
Hotel
5.0(187 Reviews)
6 Baths
172.22 ft²
- Fireplace/Heating
Breakfast- Pet Friendly
- Parking
AU $297/Night
7 Nights - AU $2,078
House
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $292/Night
7 Nights - AU $2,041
Hotel
9.8(7 Reviews)
1 Bath
- Child Friendly
- Laundry
Guest Services
AU $287/Night
7 Nights - AU $2,005
House
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $280/Night
7 Nights - AU $1,963
Hotel
8.4(106 Reviews)
4 Baths
292.78 ft²
- Private Pool
- Hot Tub
- Pool
- Breakfast
AU $267/Night
7 Nights - AU $1,868
Chester Pet Friendly Vacation Rentals
House
5.0(4 Reviews)
4 Bedrooms
5 Baths
8 Guests
4000 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
AU $712/Night
7 Nights - AU $4,985
Hotel
8.7(72 Reviews)
1 Bath
301.39 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Parking
AU $212/Night
7 Nights - AU $1,486
Hotel
7.0(890 Reviews)
1 Bath
- Fireplace/Heating
- Breakfast
- Pet Friendly
- Parking
AU $130/Night
7 Nights - AU $909
Hotel
7.8(204 Reviews)
6 Baths
396.47 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Parking
AU $177/Night
7 Nights - AU $1,239
Hotel
7.8(191 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
AU $162/Night
7 Nights - AU $1,135
Hotel
7.4(117 Reviews)
8 Baths
355.21 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
AU $159/Night
7 Nights - AU $1,114
Hotel
7.1(223 Reviews)
5 Baths
- Pool
- Pet Friendly
- Parking
- Air Conditioner
AU $108/Night
7 Nights - AU $758
Hotel
5.6(364 Reviews)
6 Baths
258.33 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
AU $140/Night
7 Nights - AU $980
Chester Large Vacation Homes
House
5 Bedrooms
3 Baths
12 Guests
4500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $855/Night
7 Nights - AU $5,986
Why Choose Rent By Owner for your Chester Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Chester Vacation Rentals
Where are the best neighborhoods to stay in Chester?
When planning your stay in Chester, Virginia, exploring the neighborhood options can greatly enhance your visit. The area offers a variety of welcoming communities that provide convenient access to local attractions and amenities. Choosing the right neighborhood to stay in can ensure a comfortable and enjoyable experience, whether you're seeking a peaceful retreat or a lively atmosphere. With a range of well-maintained vacation rentals available, you can find a property that suits your preferences and makes your trip memorable. Trust in a seamless booking process to help you discover the perfect place to call home during your time in Chester, Virginia.
North Chesterfield
In this area, you’ll find a peaceful neighborhood that offers easy access to Richmond’s amenities while maintaining a suburban charm. It’s an ideal choice if you seek comfortable vacation rentals near the region’s key attractions and conveniences.
View 183+ Rentals in North ChesterfieldBest Times to Visit Chester
When should you plan your Vacation Rentals stay?
To make the most of your experience here, consider visiting during the shoulder seasons when you'll enjoy fewer crowds and more favorable weather for exploring the area’s natural beauty and local attractions.
Peak Season Highlights
Spring (March to May)
During spring, you can enjoy pleasant weather and blooming landscapes, making it an ideal time to explore the area’s scenic beauty. This season attracts visitors looking for comfortable temperatures and outdoor activities in Chester, Virginia.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Fall (September to November)
Autumn offers cooler temperatures and vibrant foliage, perfect for sightseeing and outdoor adventures. Many travelers choose this season to experience the region's natural charm with moderate weather conditions.
Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
Off-Season Highlights
Winter (December to February)
In winter, the area tends to be quieter, providing a peaceful retreat amid cooler temperatures. It’s an excellent time for those seeking solitude or a cozy getaway in the region’s quiet surroundings.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Summer (June to August)
Summers bring warmer weather and longer days, attracting visitors who enjoy outdoor activities and warm evenings. It’s a lively season, but travel costs may be higher, and accommodations fill quickly.
Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F
Weekly Weather Forecast for Chester
How to Book Your Chester Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Chester
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for meals under the stars in this region's pleasant climate.
- Relax by a private or shared swimming pool, ideal for cooling off during warm summer days here.
- Take advantage of spacious decks or patios that offer scenic views of the surrounding landscape.
- Make use of well-maintained gardens or lawns for outdoor recreation or family gatherings.
- Benefit from access to outdoor fire pits or fireplaces to cozy up during cooler evenings.
- Experience the convenience of designated parking areas for easy access to your rental property.
- Explore nearby hiking or walking trails that allow you to enjoy the area's natural beauty firsthand.
Top Attractions Around Chester
What attractions are nearby?
While staying in this destination, you can enjoy a variety of outdoor activities, cultural experiences, and local parks that showcase the charming character and natural beauty of the region.
Family Activities
- Virginia State University Botanical Gardens: Enjoy a family stroll through beautifully maintained gardens that showcase a variety of native plants and offer educational opportunities for all ages.
- Pocahontas State Park: Experience outdoor adventures with hiking, picnicking, and playgrounds nestled within the scenic landscape of this popular regional park.
- Chesterfield County Fairgrounds: Attend seasonal events, fairs, and community festivals in the area, providing fun activities suitable for children and families alike.
- Historic Chester: Discover local history by exploring charming downtown streets, museums, and historical sites that offer engaging activities for the entire family.
Adult Activities
- Historical Sites Tour: Explore the rich history of the area by visiting key historical landmarks and museums that offer insights into its colonial past.
- Golfing Experience: Enjoy a round of golf at one of the region’s scenic courses, perfect for relaxing and engaging in friendly competition amidst beautiful landscapes.
- River Activities: Engage in kayaking or paddleboarding along the local river to appreciate the natural beauty and tranquil surroundings of this destination.
- Shopping and Dining: Discover charming boutiques, antique shops, and local eateries that showcase the area's unique character and culinary delights.
Other Places to Stay in Chester, VA
Iron Bridge Sports Park
Bermuda Hundred
Bermuda
Presquile National Wildlife Refuge
Parker's Battery Park
Henricus Historical Park
Dutch Gap Conservation Area
The Lazy Daisy
Woodvale
Point of Rocks Park
Chester Travel Tips
How Can You Make the Most of Your Stay?
- Explore local attractions early: Take advantage of the area's well-known spots to plan your days efficiently and maximize your experience here.
- Choose a centrally located vacation rental in Chester, Virginia: Staying near key sites ensures convenience, saving you time and enhancing your overall visit.
- Engage with regional events and activities: Check out the local calendar for festivals or outdoor activities that can enrich your stay at this destination.
- Prioritize comfort and amenities: Select a property with features tailored to your needs to enjoy a relaxing and hassle-free visit to this part of Virginia.
Transportation Options
- Interstate 95 Road Access: This major highway provides quick and easy connections to the surrounding region, making travel to and from Chester convenient for road travelers.
- Richmond International Airport: Situated nearby, this airport offers domestic flights that simplify your arrival and departure when visiting here.
- Local Bus Services: Public bus routes in the area offer an affordable transportation option for exploring Chester and its neighboring communities.
- Car Rentals and Taxis: Several car rental agencies and taxi services are available locally, ensuring you can navigate the region comfortably during your stay.
Local Customs Options
- Southern Hospitality: You’ll notice the warm and welcoming attitude of locals, reflecting the region’s deep-rooted Southern hospitality that makes visitors feel at home.
- Participating in local festivals here offers a glimpse into cherished traditions and a chance to celebrate the area's vibrant community spirit.
- Historic Preservation: Respect for the region’s history is evident through the careful preservation of buildings and landmarks, offering you an authentic experience of its past.
- Local Cuisine Customs: Savor the regional flavors by trying traditional dishes that highlight the area's culinary heritage during your stay.
Frequently Asked Questions About Chester?
1. What are the top vacation rentals in Chester?
There are a lot of options in Chester. If you plan on staying in the Chester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chester:
- Home2 Suites By Hilton Richmond Chester
- Hampton Inn by Hilton Richmond Chester
- Home2 Suites by Hilton Richmond Chester
- Hampton Inn By Hilton Richmond Chester, VA
- Candlewood Suites Chester Richmond by IHG
- Recline at Timberline! Family friendly!
- Residence Inn Marriott Chester
- Candlewood Suites Chester - Richmond by IHG
- Game Room + Yard: Updated House in Chester!
- Game Room + Yard: Updated House in Chester!
2. How many vacation rentals have private pools in Chester?
There are 3 vacation rentals with private pools near Chester. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Chester are best for families?
If you are looking for a family-friendly vacation home in Chester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester:
4. How many Rentbyowner vacation rentals are available in Chester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 67 in the Chester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chester.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by listing, so it’s important to review the specific rental’s policy before booking. For detailed information, consult the property’s cancellation terms or contact the owner directly.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or other costs are typically listed on the property details page. Be sure to review these fees carefully before confirming your reservation to avoid surprises.
7. How do I confirm my reservation and what are the payment options?
Reservations are confirmed through the booking platform with secure payment options. Payment methods often include credit/debit cards or other digital payment systems, but always check the listing for specific details.
8. Is there a minimum stay requirement for vacation rentals in this region?
Many properties have minimum stay requirements that can vary depending on the season or property owner preferences. You can find this information in the listing details or by reaching out to the host directly.
9. What amenities and features can I expect from a vacation rental in this destination?
Amenities vary among listings, but common features include Wi-Fi, parking, and fully equipped kitchens. To ensure the property meets your needs, review each listing’s amenities section or contact the owner for more details.
Chester Top Rated Vacation Rentals
Hotel
10.0(4 Reviews)
1 Bath
- Private Pool
- Pool
- Child Friendly
Wheelchair Accessible
AU $235/Night
7 Nights - AU $1,642
Hotel
9.0(393 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $247/Night
7 Nights - AU $1,729
AU $200/Night
7 Nights - AU $1,398
AU $203/Night
7 Nights - AU $1,421
Hotel
8.4(529 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
AU $226/Night
7 Nights - AU $1,579
Hotel
8.2(437 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
AU $229/Night
7 Nights - AU $1,604
Hotel
8.1(286 Reviews)
2 Baths
301.39 ft²
- Private Pool
- Pool
- Air Conditioner
- Child Friendly
AU $214/Night
7 Nights - AU $1,498
AU $103/Night
7 Nights - AU $725
