
House holiday rentals in Chester
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Top-rated house rentals in Chester
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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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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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Bright, quirky bungalow
Take it easy at this unique and tranquil home within 3 miles of downtown Richmond, VCU and the Fan (also close to I 95/64 exits). Located in the historic Bellevue neighborhood with restaurants and shops within walking distance, this charming Arts and Crafts bungalow has an open feel with a large family room and dining room, a kitchen with a tin-plated ceiling, a butcher block island, and breakfast nook. There are 2 Bedrooms, an office and large front and back porch perfect for morning coffee!
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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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❤️ Amazing Richmond Stay w/ King and Queen Beds❤️
Enjoy a stylish experience at this centrally-located place. Welcome to our newly renovated home where modern charm meets cozy elegance. Every detail in this home was crafted with your experience in mind and will serve as the perfect haven from which to explore Richmond, VA. Ideally located in a quiet and peaceful neighborhood of the West-End of Richmond but also conveniently minutes away from all major Highways, Downtown Richmond, local Breweries, Restaurants, Parks, Museums and Shopping.
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Petersburg Home away from Home
Brick rancher with Tv/xfinity flex, wifi, ring camera system/new kitchen/bathroom, totally remodeled stainless steel refrigerator, stove, microwave, and dishwasher. Central heat and AC with ceiling fans in every room. Laundry room for your convenience that leads out to a screened porch and fenced in backyard. Six miles from Fort Gregg-Adams Military Base. Four miles from Virginia State University. Seven miles from Virginia Motorsports Park.
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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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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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Cozy 3 bedroom home near Downtown
With 2 queen beds, 1 double and 1 twin, this house makes for a very comfortable get away. There are several smart TVs around the house. The wifi and cell service is very strong in this area. The whole group will enjoy easy access to all of Richmond’s iconic attractions from this centrally located home. We do not allow parties at this location.
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Popular amenities for Chester house rentals
House rentals with a pool

Entire Home • Central Richmond • Free Parking
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Historic Blanton Getaway
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The Resort
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Spacious Oasis on Monument Ave | Pool NOW OPEN
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Richmond Home with Pool, 5 Mi to Downtown!
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A house you wish you called home
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The Get-Together
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Pet-Friendly Home w/ Private Pool
Weekly house rentals

1830's House in Historic Old Towne Petersburg, VA
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Pristine updated rowhome with garage
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The Spruce House
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The Greenhouse 'n the Heart of Midlothian, VA
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Cozy Cape Close to the City!
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Waterfront Escape | Hot Tub, Canoe & SUP
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Charming Retreat w/ Pool Table in Chesterfield!
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The House on the River!
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Private house rentals

Pink Door-Chesterfield Va
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Nala's Place
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Exquisite Farmhouse Style Home
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Pennwood Place - The Place to Stay!
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Spacious home near downtown RVA
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The Birdhouse - Cozy Cottage Retreat in Richmond
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Pet-Friendly in Petersburg, VA
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Fenced Yard, Swing Set: Pawfect for Family & Dogs!
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Destinations to explore
- New York City Holiday rentals
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- Washington Holiday rentals
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- Virginia Beach Holiday rentals
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- Kings Dominion
- Water Country USA
- 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
- Virginia State Capitol-Northwest
- American Civil War Museum
- Metro Richmond Zoo
- Jefferson Park





