
House vacation rentals in Chester
Find and book unique houses on Airbnb
Top-rated house rentals in Chester
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!
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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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The Spruce House
The Spruce House is a cozy 1960's rancher, ideal for tourists who loves to explore historic places, traveling health workers, business and workers on special projects, sports tour for local tournaments. The simplicity of this house will welcome you during your stay. Nestled at the heart of the city, but when you look out in the windows, you will enjoy the tranquility of the countryside, the twitting of the birds in the rain forest and the backyard designed to look like a campsite.
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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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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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Cozy Cape Close to the City!
Enjoy a relaxing experience in a quiet neighborhood conveniently located less than a 10 minute drive to the city! This location is perfect for any traveling nurses who are going to McGuire VA hospital or anyone looking to experience all that the city of Richmond has to offer! Located right outside of the city and close to several highways it is a great location for everyone looking to stay in the area!
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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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Luxury stay in Prince George
Experience the ultimate blend of luxury, style, and family friendly relaxation during your stay in Prince George, Virginia. This retreat is the perfect place to create lasting memories with your loved ones. Located only 10 minutes from Fort Lee. We do allow small gatherings and events for an additional fee. Ask us how.
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Single family‼️Fenced/ 3TV/3 mins to I-64 & I-95
Welcome to our peaceful and cozy house! Newly renovated in 2022! Hosts up to 8 people comfortably ! Peaceful fully fenced backyard! Enjoy the patio with fire pit! Plenty of free street parking! Minutes from everything! Pet friendly! Fully equipped kitchen with appliances!
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Popular amenities for Chester house rentals
House rentals with a pool

Historic Blanton Getaway
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YOU FOUND IT! Walkable paradise

A house you wish you called home
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Historic Marshall House 11 plus beds
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The Resort
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Spacious Oasis on Monument Ave | Pool NOW OPEN
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The Get-Together
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Entire Home • Central Richmond • Free Parking
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Weekly house rentals

Spacious home near downtown RVA
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Pennwood Place - The Place to Stay!
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Gorgeous historic home in the heart of the Fan
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Urban Farmhouse w/ Swings, FirePit & Putting Green
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Historic & Charming House in the heart of RVA!
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The House on the River!
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Cozy Northside Nook only 10 mins from Downtown RVA
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Waterfront Escape | Hot Tub, Canoe & SUP
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Private house rentals

Pet-Friendly in Petersburg, VA
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The Birdhouse - Cozy Cottage Retreat in Richmond
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Nala's Place
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Pink Door-Chesterfield Va
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Charming Retreat w/ Pool Table in Chesterfield!
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Charming, Private Abode: Serenity in Hopewell, VA!
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Brand-New Boho Family Getaway!
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Recline at Timberline, Family friendly!
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Destinations to explore
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- Busch Gardens Williamsburg
- Kings Dominion
- Water Country USA
- Pocahontas State Park
- Jamestown Settlement
- Greater Richmond Convention Center
- Brown's Island
- Colonial Williamsburg's Merchants Square
- Libby Hill Park
- The Poe Museum
- The National
- Forest Hill Park
- Virginia Holocaust 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
- The Diamond





