
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!
LocationValueCleanliness

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.
ValueFamilyView

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
LocationFamilyCleanliness

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.
LocationFamilyCheck-in

4 beds/3 Private parking/2 mins to I-64 & I-95
Your family will be close to everything when you stay at this centrally-located place with a 92 walk score. 3 minutes to VCU, 7 minutes to Scott’s Addition Historical District and 2 minutes to I-64/95. New house built in 2016. Hosts up to 8-9 people comfortably Dripping coffee & Keurige coffee machine and coffee pods are provided! Pet friendly! Crib& high chair and kids dishes are provided for kids! This place is great for families with kids,couples,solo adventures,business travelers.
LocationValuePets

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!
FamilyLocationHiking

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*
ValueLocationHiking

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!
FamilyValueOutdoor 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.
FamilyValueCondition

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.
FamilyLocationCleanliness

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.
FamilyValueAmenities

Modern 5 Bedroom Home, 5 mins away from Downtown
This home is all about location, with my bike I can get to work downtown within 10 mins, pedal to Tabol Brewery for 2 mins or just cross the street to play golf. The 1900 Square feet are divided into 5 rooms, 3 bathroom and an amazing open concept great room. Keyless entry and 24/7 outdoor security cameras are installed. Two private parking spots. @5bedsrva
LocationFamilyBathroom
Popular amenities for Chesterfield County house rentals
House rentals with a pool

Historic Blanton Getaway
ValueFamilyBackyard

Entire Home • Central Richmond • Free Parking
ValueFamilyKitchen

Pet-Friendly Home w/ Private Pool
ValueFamilyCondition

A house you wish you called home
ValueLocationComfort

The Get-Together
FamilyLocationCleanliness
Weekly house rentals

Close to everything and quiet - STR Permit 129294
ValueLocationComfort

Snug in Carver
FamilyValueOutdoor spaces

Big Fan Home/private parking /6 BR & 4 BA
ValueFamilyBathroom

The House on the River!
FamilyLocationSleep quality

Waterfront Escape | Hot Tub, Canoe & SUP
FamilyLocationComfort

Stay Awhile - Private, Large Yard, Easy Travel
FamilyLocationLaundry

Pennwood Place - The Place to Stay!
LocationFamilyCleanliness

AllSeaZens Oasis
FamilyLocationOutdoor spaces
Private house rentals

Nala's Place
ValueFamilyKitchen

Stephanie's Peaceful Place.
FamilyLocationIndoor spaces

Exquisite Farmhouse Style Home
LocationFamilyParking

The Happy Place
LocationFamilyCleanliness

Qualla Park
LocationFamilyAccuracy

Brand-New Boho Family Getaway!
ValueLocationComfort

Large Family Home in Safe & Accessible Area!
FamilyLocationCleanliness

The Villa on Falling Creek.
FamilyLocationWi-Fi
Destinations to explore
- Hotel rooms Chesterfield County
- Rentals with pools Chesterfield County
- Pet-friendly rentals Chesterfield County
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- Rentals with breakfast Chesterfield County
- Family-friendly rentals Chesterfield County
- Rentals with a hot tub Chesterfield County
- Serviced apartment rentals Chesterfield County
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- Rentals with lake access Chesterfield County
- House rentals Virginia
- House rentals United States
- Kings Dominion
- Pocahontas State Park
- Jamestown Settlement
- Greater Richmond Convention Center
- Brown's Island
- The National
- Libby Hill Park
- Forest Hill Park
- Colonial Williamsburg's Merchants Square
- Virginia Holocaust Museum
- The Poe Museum
- Altria Theater
- Science Museum of Virginia
- Children's Museum of Richmond
- Virginia State Capitol-Northwest
- American Civil War Museum
- Metro Richmond Zoo
- Jefferson Park
- Hollywood Cemetery
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