
Holiday rentals in Chester
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness and more.

Heron Rock: Lakefront Cottage on Lake Chesdin
Enjoy peaceful lakefront living at Heron Rock Cottage, where you can stroll through the woods, swim or fish off the dock, paddle the lake in kayaks, or simply relax and enjoy the wildlife and beautiful sunsets. Situated on 6 acres in Dinwiddie County, this newly renovated cottage includes 2 bedrooms, full bath, full kitchen, living room with fireplace and private patio with dining area. Your stay includes full access to the grounds and dock and you are welcome to tie up a boat if you bring one.

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.

The Henry Lofts Unit 1 - 'Chloros Lux Collection'
The Henry Lofts studio provides style, convenience, exposed brick & an open floor plan with 800 sq. ft. You will find a fully fenced pet friendly yard to go along with your private parking, & accommodated apartment with all new everything. This historic building was built in the 1800's but completely renovated with all new appliances and systems in 2024! Walk to all of the local breweries, restaurants, museums, galleries, and boutiques in downtown Old Towne Petersburg, VA. Private Deck/Patio

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.

Spacious home near downtown RVA
Discover comfort and convenience in our centrally located Airbnb nestled in the heart of the greater Richmond area. Perfectly situated within walking distance to a serene park and soccer fields, it's an ideal retreat for nature lovers and sports enthusiasts alike. Plus, we warmly welcome your furry friends, as our dog-friendly abode boasts a secure fenced backyard for their enjoyment. Book your stay now and experience the best of Richmond's charm and hospitality!

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.

$ Cozy 1BR 1BA Apartment: Near Fort Gregg-Adams $
Welcome to our newly remodeled private apartment with 2 separate entrances. Enjoy a dedicated workspace, 2 smart TVs with free Roku, and proximity to Fort Gregg Adams, dining, and shopping. Stay secure with keyless entry and exterior cameras. Fully equipped kitchen, off-street parking, and adjustable thermostat included. Rest peacefully with blackout curtains and a Queen-size bed. Welcome to your home away from home!

Cozy Hideaway guest suite
"The Hideaway" is a spacious and cozy, ground level basement guest suite with easy access to everything in Midlothian. This space offers a convenient, private entrance from the driveway, washer/dryer, high speed internet, 65" smart tv with free Peacock, Netflix, Hulu, Disney, ESPN, Max, Discovery Plus, Paramount, Prime Video, to just name a few. Shared access to the fenced in back yard with a grill and firepit.

Kindness Sweet
** check in will be after 5 with an extension of checkout at 12. TY) Private suite for Max of 2 ($10 for 2) Connected to the main house, where the owner lives. Separate entrance is behind the home (yellow dr) that leads through a laundry room into your space. Down the drive, around the house. Great for traveling nurses, etc. HenricoDr, St.Mary's, & VCU. We welcome paying guests only that are respectful.
Popular amenities for Chester holiday rentals
Stay near Chester's top sights
Other great holiday rentals in Chester

Calm&Cozy: Private Bed+Bathroom

Hopewell Retreat, close to Fort Gregg-Adams

• Private Room in Charming Cottage 5 mins from RVA

Modern Cozy / Pool Access, Wi-Fi, I-95 & Fort Lee

XL Private Room | Queen Bed + 55" Smart TV

Richmond Museum District; close to everything!

Tranquility in the City

Comfortable, convenient private bed & shared bath
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 83 | € 83 | € 68 | € 76 | € 76 | € 83 | € 72 | € 76 | € 72 | € 83 | € 69 | € 83 |
| 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 wifi, over 20 homes with air conditioning, 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 holiday rentals in Chester

Total holiday rentals
Explore 30 holiday rentals in Chester

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

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

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Chester holiday rentals include wifi 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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