
House holiday rentals in Chesterfield County
Find and book unique houses on Airbnb
Top-rated house rentals in Chesterfield County
Guests agree: These houses are highly rated for location, cleanliness and more.

Luxury BOHO upper unit
Relax in this calm, stylish 3 bedroom/2 full bath upper level unit. Another Airbnb is in the finished basement unit. The space is completely yours and no access to the other basement unit. Only shared area is the back deck. Unit has a completely updated kitchen with stainless steal and granite. Master bedroom has a super comfy queen bed and a master bath that has a beautiful walk in shower. Guest room has another queen bed and office area has a futon. Elegance and romantic boho style throughout!
LocationFamilyView

Open 2 acre, Huge yard/drive, K, K, Q bed, 2 bath
Private and spacious 3 bedroom, 2 full bath home on 2 acres. Less than 10 mins to Airport, Winery, Food and Shops Fully equipped kitchen for your cooking needs. Huge driveway and yard to turn around large vehicles, or boat trailers. Plenty of space to unwind and relax while enjoying Deer and other animals passing by. 10 minutes from Richmond Airport (RIC), VA Capital Bike Trail, River Dog Winery, local recreation park and shopping. 15 minutes to Downtown Richmond. 45 minutes to Williamsburg.
FamilyValueBackyard

Close to everything and quiet - STR Permit 129294
Your family will be close to everything when you stay at this centrally-located home in the Oxford Section of Richmond. Just 10 minutes from downtown and minutes from the James River for kayaking and exploring. Plenty of room for family or a great place to work. Office desk /chair in own office - now with 1Gb Fios! Two Amazon TVs in separate area to keep everyone happy. Fenced in area of back yard/swing set for little ones and a patio for relaxing under the shade of oaks and patio umbrella.
LocationValueAmenities

Private Garden Home w/ Large Fenced Yard + Gazebo
Experience Casa Terra, a one-of-a-kind historic home in the urban heart of Richmond, Virginia. Tucked away on a sprawling 1/3 acre property just ten minutes from downtown, this thoughtfully restored 1928 Craftsman bungalow blends timeless character with natural calm. Designed for couples, small families and furry companions, Casa Terra features a 6ft fully fenced backyard where dogs can play beneath the branches of a 100-year-old willow oak while guests unwind in the gazebo or around the fire.
LocationFamilyParks

Hot Tub Oasis, Minutes from Downtown Richmond
Find the best of both worlds here, a tranquil getaway while only 12 minutes from Downtown, Carytown, Scott's Addition, the VMFA, and more. Enjoy the James River by Tubing, Kayaking, Rafting or Swimming, Hiking, Award Winning Restaurants, all within a 5 minute drive. Our home includes amenities such an 8 person hot tub, a pond dock with beautiful views, outdoor fire pit, patio, essential oil bath, and tea/ coffee on us! Our kitchen is stocked with cookware, spices, & dishes. STR-135430-2024 is
FamilyLocationAccess

Snug in Carver
Right in the heart of Carver, we're just blocks from VCU, the Altria Theater, and Monroe Park. We're also THE closest Airbnb to the interstate in the city of Richmond. If you're getting off 95/64 in the evening, you can slip right back on in the morning in about 90 seconds flat! We're just a hop-skip from downtown and all that has to offer. Stroll down through the First Friday gallery walk, or enjoy all the delicious restaurants and bars Jackson Ward and Broad St. have to offer.
LocationFamilyIndoor spaces

1830's House in Historic Old Towne Petersburg, VA
This circa 1830 storefront home was recently renovated. The second floor living quarters, fully furnished with a gourmet kitchen, super living room, study, large master bedroom and bath complete with antique claw-foot bathtub, sliding warehouse doors and much more can be yours for a surprisingly low price. Complete with original pine flooring and furnished with a combination of old and new touches. Walking distance to historic Old Towne Petersburg and ten minutes to Fort Lee.
LocationValueCleanliness

Pristine updated rowhome with garage
*Sunday checkout at 3 pm* Located in the heart of historic Richmond and within a short walking distance to the James River, Brown's Island, Belle Isle, downtown, Altria Theatre, and VCU. This comfortable, spacious, and beautiful rowhome in eclectic Oregon Hill awaits your visit and is painstakingly furnished with Airbnb guests in mind. All of your day-to-day needs are met so you can relax and enjoy your time! - Walk score: 73, very walkable. Thanks for your consideration!
LocationFamilySleep quality

Renovated Modern Home Minutes to Downtown Richmond
Welcome to your bright, peaceful, spacious retreat, while only 15 minutes from Downtown, Carytown, Scott's Addition, the VMFA, and more. And only a 4 minute drive to Trader Joe's! Local hikes, restaurants and Chesterfield mall, all within a 7 minute drive. Your kitchen boasts all brand new appliances and plenty of new cookware. Local sightseeing, brewery & eatery guides provided. *Note: Carbon monoxide alarm not present because the house runs entirely on electric*
ValueFamilyAir conditioning

HideawayOasis/VSU/95/FortGreggAdams/FirePT/PoolTBL
Welcome to Our Hidden Oasis! 🌿✨ This cozy retreat is designed with love and thoughtfulness, perfect for small families and intimate connections. Enjoy year-round outdoor fun—roast s’mores by the fire pit, relax on the patio, or challenge friends to a game of pool. Sleep soundly in our comfy beds and wake up refreshed for new adventures. Whether unwinding or making memories, this home is your perfect getaway. We can't wait to host you!
ValueLocationOutdoor spaces

The Cottage in the City -Private Yard and Fire Pit
Your family will be close to everything when you stay at this peaceful, centrally-located home. This home is equipped with anything you may need during your stay! Enjoy the beautiful naturally lit living room throughout the day, or stargaze in the back yard while enjoying gentle heat from the firepit. The best part? We are a quick drive to anything you may be looking to do in Richmond and only 12 minutes to downtown center city.
FamilyLocationGetting around

The Greenhouse 'n the Heart of Midlothian, VA
The Greenhouse is a whimsical refuge located in the very heart of Old Midlothian Village with its old churches and historic houses and is within a 15-20 minute walking distance from several restaurants. You will love staying in our nature inspired home with its resort inspired furnishings; green, leafy décor, fully equipped kitchen, large bathrooms, stocked laundry room, and large yard with gas grill, picnic table and fire pit.
LocationFamilySleep quality
Popular amenities for Chesterfield County house rentals
House rentals with a pool

Entire Home • Central Richmond • Free Parking
FamilyValueGetting around

Historic Blanton Getaway
ValueFamilyKitchen

A house you wish you called home
FamilyLocationWalkability

The Get-Together
ValueLocationDecor

Pet-Friendly Home w/ Private Pool
Quiet
Weekly house rentals

King Bed + Walkable to Shops & Free Parking
FamilyValueHeating

Sweet Little Home 2
LocationFamilyParking

Cozy Cape Close to the City!
ValueLocationLayout

Richmond Heartthrob: A Stylish River City Retreat!
ValueFamilyAccess

The Spruce House
LocationFamilyBackyard

Spacious and Beautiful Home with Outdoor Kitchen
FamilyLocationCleanliness

Pink Door-Chesterfield Va
LocationFamilyCheck-in

Waterfront Escape | Hot Tub, Canoe & SUP
FamilyLocationDecor
Private house rentals

Qualla Park
LocationFamilyHiking

Recline at Timberline, Family friendly!
LocationValueCheck-in

Equine Country Living 'n Powhatan, VA: Rusmar Farm
LocationFamilyHospitality

Stephanie's Peaceful Place.
FamilyValueSleep quality

Stay Awhile - Private, Large Yard, Easy Travel
LocationFamilyOutdoor spaces

AllSeaZens Oasis
FamilyLocationQuiet

The Birdhouse - Cozy Cottage Retreat in Richmond
LocationFamilyKitchen

Welcome to Mojo Dojo Casa House
LocationFamilyAccuracy
Destinations to explore
- Pet-friendly rentals Chesterfield County
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- Kings Dominion
- Pocahontas State Park
- Jamestown Settlement
- Greater Richmond Convention Center
- Brown's Island
- Libby Hill Park
- Forest Hill Park
- Colonial Williamsburg's Merchants Square
- The National
- Virginia Holocaust Museum
- The Poe Museum
- Altria Theater
- Science Museum of Virginia
- Hollywood Cemetery
- Children's Museum of Richmond
- Virginia State Capitol-Northwest
- American Civil War Museum
- Metro Richmond Zoo
- Jefferson Park
- Things to do Chesterfield County
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- Tours Virginia
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