
Vacation rentals in Chester
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Top-rated vacation rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness, and more.

Charming, Private Abode: Serenity in Hopewell, VA!
Welcome to our private 1 bedroom, 1 bathroom abode! Our charming home is the perfect place for your stay in the heart of Hopewell, VA. Ideal for a couple’s retreat, a couple of friends or a solo traveler. Conveniently located near popular attractions, dining options & shops. With its cozy & cool atmosphere, you'll feel right at home during your stay. We look forward to hosting you at our home, where comfort & convenience await. Book your stay today & enjoy a memorable experience in Hopewell, VA!

The Henry Lofts Unit 3 - 'The Sunset Suite'
The Henry Lofts Unit 3 apartment provides everything you could possibly want; elegance, style...conveniently located in downtown Old Towne Petersburg & 3 miles from Fort Gregg-Adams. Bring your furpal because you have a fully fenced pet friendly yard with a private deck to let your dog outside, along with private parking. This historic building was built in the 1800's & completely renovated with new appliances in 2024. Walk to the local restaurants, museums, and coffee shops in your back yard!

Green Door Escape
Forget your worries in this spacious and serene space. Enjoy a comfortable stay with a private entrance, separate from the main house, with parking at your front door. Privacy prevails! A comfortable home away from home. Access to a lush garden. Queen bed, private en-suite bathroom with shower. Fitted kitchen: Induction-stove ( two plate), Air-fry Microwave, Coffee maker, and Refrigerator. Crockery, cutlery, cookware and utensils, provided. Basic cleaning supplies. Linen changed weekly.

Lulu's Peaceful Cottage
Enjoy a relaxing stay at this great located cottage. Lulu's Peaceful cottage is brand new, stylishly decorated for comfort. Private little cottage in a park like setting amongst trees & nature. Inside is an equipped kitchenette, coffee/tea bar, & is meal prep friendly. Relax in the soaking tub, or shower if you prefer. Lulu's is close to everything. Shopping, gyms, parks, & recs, hospitals, museums, & airport, and just a few miles from all major highways. Easy driveway parking & keyless entry.

Stay Awhile - Private, Large Yard, Easy Travel
Welcome to the Exurbs! Peaceful property, not quite rural, not quite the suburbs. Still close enough to jump on the interstate and get where ever you need to be fairly quicky. This property has a huge fully fenced back yard, with plenty of room to unwind and relax on the front/back porch. Bring your boats and trailers, plenty of room! Interstate 288: 3 min Interstate 95 Interchange: 5 min Defense Supply: 6 min Chester: 10 min Dutch Gap Boat: 13 min RIC Airport: 20 min Fort Gregg: 20 min

Peaceful & Cozy Stay Near Richmond
Discover our brand-new Airbnb unit, designed for comfort and style! This stunning new construction features 3 spacious bedrooms, 2.5 modern bathrooms, a private balcony and a gorgeous kitchen with a sleek island. Enjoy the convenience of a garage in-unit, laundry and all-new furniture for a fresh and luxurious experience. Relax with the whole family at this peaceful place to stay. Mastersuite features a remote-controlled reclining bed on the main floor and two bedrooms on the second floor.

Private guest apt on creek w/ patio & fire feature
“The Nest” is a completely private, ground level “basement” apartment. 15 minutes from downtown Richmond & 18 minutes to Pocahontas State Park, this space offers a peaceful, conveniently located, retreat. Private entrance, cozy patio, & large yard- all creek side and professionally designed. Laundry in unit, high speed internet, Smart TV. Yard is wooded and private. Many restaurants and tons of shopping within 5 min of the house, and 2.5 miles from highway access.

Gorgeous Creek View from your Private Eyrie
Enjoy a relaxing view of Falling Creek from the second floor apartment with a private entrance and balcony. The wall of windows overlooks a secluded backyard with visiting deer, heron, owls, and other wildlife. Sit by the pond, creek or fire pit. The property offers off street parking in a safe neighborhood which is located 20 minutes from downtown Richmond, 10 mins to Midlothian and Chesterfield, 3 mins to Swim RVA. 15 mins to the airport or train station.

Funky & colorful private guesthouse with parking!
This unique place has a style all its own with carefully curated touches of yellow! A private guesthouse tucked away and at the top of a spiral staircase. This space is a five minute drive from Richmond's most popular neighborhoods. Fully equipped with a mid-century modern kitchenette, private patio, and A/C! This space is an experience in itself. Explore Richmond's best kept secret; the Yellow Tiger's Den.

The Creekside Cool Bus
Experience the ultimate glamping adventure in our converted school bus! Nestled on 5 acres of land, the campsite features lush woods and a creek. Enjoy the peace and quiet of nature with the comfort of a home away from home. Our skoolie is the perfect basecamp for outdoor adventures-just 30 minutes to Richmond and 5 minutes from the nearest trailhead at Pocahontas State Park with pass included.

GALLERIA SOUTH minutes away from Downtown RVA!
Welcome to our stylish Galleria inspired home, in South Side Richmond VA. You will experience a true essence of local artists and how they inspire our community! Galleria South is centrally located for everything in Richmond Virginia. We are only 5 minutes away from the James River and Forest Hill. And located about 10 minutes from Church Hill, Downtown, Carytown, The Fan, & Museum District!

Brand new, beautiful home.
This new built home, with 1570 sf , fresh from driveway to kitchen, welcomes you. Come, Relax with the whole family at this brand new elegant, peaceful place to stay. The house is in a quiet, peaceful Chester neighborhood, minutes from Amazon warehouse, Capital One, Lego Land. Cinema Cafe, Fort Greg-Adam, Richmond downtown, Richmond Airport are less than 30’. You’ll love it.
Popular amenities for Chester vacation rentals
Stay near Chester's top sights
Other great vacation rentals in Chester

Comfort & Style Near Fort Lee and VSU

4

Private room in a sparkling-clean, quiet home!

• Private Room in Charming Cottage 5 mins from RVA

Tucked In RVA, VCU, and Downtown

21% Monthly Off, Fresh Room at RIC, DataCenter VCU

Tranquility in the City

Charming Suite in little Farm with Goats & Alpacas
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 85 | € 85 | € 69 | € 78 | € 78 | € 85 | € 73 | € 78 | € 73 | € 85 | € 70 | € 85 |
| Avg. temp | 4°C | 5°C | 9°C | 15°C | 19°C | 24°C | 26°C | 25°C | 22°C | 16°C | 10°C | 5°C |
Frequently Asked Questions
What are the most popular amenities for House Rentals in Chester?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with air conditioning, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Chester have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Chester. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Chester?
Experience the best of Chester with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chester have free parking?
Absolutely! We offer over 20 house rentals with free parking in Chester. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Chester?
Four-legged friends are welcome in Chester. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Chester?
Yes! Work meets play with ease at over 10 vacation rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Chester have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Chester. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Chester?
Chester has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about vacation rentals in Chester

Total vacation rentals
Explore 30 vacation rentals in Chester

Nightly prices starting at
Chester vacation rentals start at € 17 per night before taxes and fees

Verified guest reviews
Over 1,720 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Chester vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chester rentals

4.8 Average rating
Chester stays are highly rated by guests—averaging 4.8 out of 5!
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