
Holiday houses 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.

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

Warm, Cozy and Comfortable Houseboat, Gated Marina
Note: Dates taken? I have one other boat online-- The Cookie B with beautiful river views. We offer no contact boarding if desired and we understand the need for a clean place to stay. Therefore we go beyond the recommended guidelines concerning sanitation by fogging the entire boat after each guests departure. And for dining, you can cook aboard or enjoy the Lily Pad Cafe, an outdoor covered and heated restaurant on the river, and it is only two miles from the marina.

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.

"Lofty Cottage" Adorable 1-Bedroom Guest House
Enjoy this quaint Cozy Cottage with bedroom loft! This adorable 1-bedroom unique place has a style all its own. Built in the 1960’s behind the main house, it has floor to ceiling pine paneling, pine floors and fireplace. It has been recently remodeled with new tiled bathroom , newly remodeled kitchen and stainless steel appliances. A new Heating and Air unit was installed summer 2021. The pine paneling and 16 foot high ceilings gives it that "cottagey" feel.

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.

Church Hill Apartment on Chimborazo Park
Location, location, location. If you are coming to Richmond for business or pleasure, Church Hill is the place to be. It is full of historic sites and hosts some of the best dining experiences in Richmond. Take a tour of St. John's Church, where Patrick Henry made his 'Give me Liberty or Give me Death' speech. Visit Chimborazo Hospital Civil War Museum. Walk to nearby restaurants, diners, bakeries, cafes, pubs, and parks.

Romantic Treehouse for 2 in Farm (no kids)
Surrounded by trees and peace in our small farm in a neighborhood, this cozy little cabin is made for secluded romantic stays and to enjoy a relaxing and restful night. Not suitable for children. Cabin is 10 X 12" of cuteness with all the amenities you might need to feel comfortable, electricity, heater, Smart TV, wifi, coffee maker, memory foam bed, and an awesome outdoor bathroom to shower under the stars!

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.
Popular amenities for Chester holiday rentals
Stay near Chester's top sights
Other great holiday rentals in Chester

4

The Hearth Room - Strawberry Hill Petersburg

Shared home w/private bed & bath in N. Churchill

• Private Room in Charming Cottage 5 mins from RVA

Tucked In RVA, VCU, and Downtown

Travel and Explore, enjoy this home with Heart

“Captain’s Quarters” in 1920’s Craftsman Home

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 | $149 AUD | $149 AUD | $122 AUD | $137 AUD | $137 AUD | $149 AUD | $129 AUD | $137 AUD | $129 AUD | $149 AUD | $123 AUD | $149 AUD |
| 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 holiday rentals in Chester

Total holiday rentals
Explore 30 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at $30 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Chester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chester rentals

4.8 Average rating
Chester stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- New York City Holiday rentals
- Western North Carolina Holiday rentals
- Washington Holiday rentals
- Jersey Shore Holiday rentals
- Myrtle Beach Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Jersey City Holiday rentals
- Cape Fear River Holiday rentals
- Busch Gardens Williamsburg
- Carytown
- Kings Dominion
- Water Country USA
- Pocahontas State Park
- Brown's Island
- Jamestown Settlement
- Royal New Kent Golf Club
- Golden Horseshoe Golf Club
- Independence Golf Club
- Libby Hill Park
- The Country Club of Virginia - James River
- Kinloch Golf Club
- The Foundry Golf Club
- Hermitage Country Club
- The Poe Museum
- Hollywood Cemetery
- Science Museum of Virginia
- Kiskiack Golf Club
- Grand Prix Raceway




