
House holiday rentals in Chesterfield County
Find and book unique houses on Airbnb
Top-rated house rentals in Chesterfield County
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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!
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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.
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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.
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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.
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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
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New Modern Unit in Historic Old Manchester.
This modern 2 bed 2 bath first floor unit in Old Manchester is great for a Richmond visit. Located near all three of Richmond's downtown bridges you can't find a better home base for your excursions. If you want to explore the river, walk to Brown's island or hop one of the bridges to the Fan, the Financial District, or Shocko Bottom, it's all minutes away. We are animal lovers and have a few of our own. If you are bringing yours, please pick up after them and not have them on the furniture.
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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.
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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!
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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!
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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.
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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.
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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.
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Popular amenities for house rentals in Chesterfield County
House rentals with a pool

The Get-Together
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Historic Blanton Getaway
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Entire Home • Central Richmond • Free Parking
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Pet-Friendly Home w/ Private Pool

A house you wish you called home
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Weekly house rentals

Pennwood Place - The Place to Stay!
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Richmond Heartthrob: A Stylish River City Retreat!
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Qualla Park
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Pink Door-Chesterfield Va
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Enjoy Breezes on the James River
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AllSeaZens Oasis
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Charming Retreat w/ Pool Table in Chesterfield!
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Snug in Carver
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Private house rentals

3 BR/2 Bth house mins from three local hospitals
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The Birdhouse - Cozy Cottage Retreat in Richmond
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Nala's Place
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Vincent House - Historic Charm & Modern Comfort
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Parkside Getaway
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Charming, Private Abode: Serenity in Hopewell, VA!
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Brand-New Boho Family Getaway!
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70's Era Loft House with Mid-Century Vibe
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Destinations to explore
- Hotel rooms Chesterfield County
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- Kings Dominion
- Pocahontas State Park
- Greater Richmond Convention Center
- Brown's Island
- Forest Hill Park
- Libby Hill Park
- Colonial Williamsburg's Merchants Square
- The National
- Virginia Holocaust Museum
- The Poe Museum
- Altria Theater
- Science Museum of Virginia
- Children's Museum of Richmond
- American Civil War Museum
- Virginia State Capitol-Northwest
- Metro Richmond Zoo
- Jefferson Park
- The Diamond
- Jamestown Settlement
- Hollywood Cemetery
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