House holiday 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.

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Superhost
A comfortable living area features a gray sectional sofa adorned with yellow cushions. A wooden coffee table rests on a patterned area rug, while a TV is mounted on the wall. The room displays a welcoming sign that reads 'Welcome to Carver Industrial Historic District.'
Home in Carver
4.85 out of 5 average rating, 266 reviews

Historic Home by Siegel Center

Enjoy a one of a kind historic experience at this centrally-located home near the Carver Industrial Historic District of Richmond! Centrally located, directly across from the Seigel Center, this 120+ year old property has been completely renovated including a new kitchen (w/ stainless steel appliances and quartz countertops), bathroom, & tile floors throughout! It is fully furnished and designed to stay true to it's historic roots while being upgraded with modern twists for a one of a kind stay!

Guest favourite
Home in Richmond
4.95 out of 5 average rating, 208 reviews

Casa Terra I Pet-Friendly Eco Oasis with Gazebo

Welcome to Casa Terra, your serene urban retreat, perfect for families & furry companions. Tucked away on a sprawling 1/3 acre, this property is a rare gem. Let your dogs run free in the 6-ft fenced backyard or lounge in the screened gazebo. Inside, unwind in the living room with a 55-inch smart TV, or cook in the remodeled chef’s kitchen with an induction stovetop and all the essentials. You'll find two queen bedrooms & a full pullout sofa for additional guests—all designed for a restful stay.

Guest favourite
A comfortable living area features a brown leather sectional couch with a matching armchair and ottoman. A round table sits on a patterned rug, while soft natural light filters through the window blinds. Two framed animal prints adorn the light-colored wall.
Home in Richmond
4.9 out of 5 average rating, 227 reviews

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!

Superhost
A sitting area features a two-tone black sofa and matching armchair, complemented by a textured orange rug. Natural light filters through sheer curtains, illuminating the space and highlighting the subtle details of the room's design.
Home in Carver
4.82 out of 5 average rating, 454 reviews

Cozy Carver Accommodations

You've found a rare unicorn! This ultra-cozy row home is perfectly placed just blocks from VCU, and a short walk to the Fan, Jackson Ward & downtown. It's also less than 2 miles from "Richmond's Playground": Scott's Addition. This 540 sq. ft. home is filled with midcentury accents, local art, granite countertops, stainless steal appliances & pine floors. It has everything you need to cook and do laundry. You can also park for free with our street parking pass. We welcome your well-trained pets!

Top Guest favourite
A modern kitchen features light-colored cabinetry and a spacious island with a marbled countertop. Stainless steel appliances are integrated, including a microwave and a coffee maker. Natural light is provided by a window above the sink, enhancing the functional layout of the space.
Home in Richmond
4.98 out of 5 average rating, 134 reviews

Private 2 acres. Huge yard/drive. 8 min to Airport

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.

Guest favourite
A bedside table is shown beside a spacious bed, topped with a vase of colorful flowers and a magazine. Soft white bedding and multiple pillows are arranged on the bed, complemented by a lamp casting a warm glow against a softly colored wall.
Home in Colonial Heights
4.97 out of 5 average rating, 101 reviews

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.

Top Guest favourite
A welcoming living room features a comfortable sectional sofa and two stylish armchairs arranged around a round coffee table. A TV is mounted above a white mantel, with a decorative plant and wall art enhancing the space. Natural light streams through large windows, illuminating the rich hardwood floors.
Home in Oregon Hill
4.98 out of 5 average rating, 146 reviews

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!

Top Guest favourite
A covered outdoor entertaining area features comfortable seating arranged around a fire pit. Soft lighting strung above creates a warm ambiance. The space is complemented by decorative plants and cushioned sofas, providing a cozy environment for gatherings.
Home in Colonial Heights
4.93 out of 5 average rating, 178 reviews

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!

Guest favourite
An open dining area features a round table surrounded by chairs, complemented by a vibrant area rug. The adjoining kitchen showcases modern appliances and bar seating. Large windows allow natural light to enhance the bright and airy space.
Home in Richmond
4.9 out of 5 average rating, 137 reviews

Classic Comfort, Minutes from Downtown RVA

Welcome to our charming 3-bedroom vintage retreat minutes away from historic Downtown Richmond, Virginia! Step into a bygone era as you cross the threshold of this thoughtfully designed home, where classic charm meets modern comfort. Our home is a tribute to the timeless beauty of yesteryears. It is just minutes from Richmond International Raceway, Convention Center, VCU, UR, and Richmond Airport!

Guest favourite
A spacious living room features a comfortable sofa adorned with black and white pillows. A flat-screen TV is mounted above a minimalist fireplace. Natural light filters through large windows, highlighting a decorative rug on the hardwood floor. A plant adds a touch of greenery to the space.
Home in Richmond
4.88 out of 5 average rating, 246 reviews

GALLERIA SOUTH minutes away from Downtown RVA!

Welcome to our stylish Galleria inspired home, in South Side Richmond VA. You will experience a true essence of local artists and how they inspire our community! Galleria South is centrally located for everything in Richmond Virginia. We are only 5 minutes away from the James River and Forest Hill. And located about 10 minutes from Church Hill, Downtown, Carytown, The Fan, & Museum District!

Guest favourite
The entrance of a historic brick home is graced by a white wooden staircase leading to a dark door. A decorative awning featuring red, white, and blue patterns drapes above the door, with planters positioned on either side. Flanking windows allow natural light to enter.
Home in Petersburgh
4.95 out of 5 average rating, 110 reviews

Historic Home Near Old Town

Private 1850's Greek Revival Home in Historic Petersburg! -Minutes away from Old Town restaurants and shopping -One block from Poplar Lawn Park -Fast wifi, dual zone central ac/heat -Newly renovated first and second floor -Sleeps up to three (couple + one or two singles) *Please read full listing before booking as not everyone will feel comfortable in our lower income neighborhood.

Superhost
A welcoming living room features a large sectional sofa and comfortable armchairs arranged around a glass coffee table. A flat-screen TV is mounted above a modern fireplace, while natural light fills the space through sliding glass doors leading to an outdoor area.
Home in Prince George
4.78 out of 5 average rating, 107 reviews

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.

Popular amenities for Chester house rentals

When is the best time to visit Chester?

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Avg. price$109 AUD$119 AUD$78 AUD$107 AUD$119 AUD$134 AUD$81 AUD$78 AUD$72 AUD$86 AUD$76 AUD$112 AUD
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Quick stats about house rentals in Chester

  • Total holiday rentals

    Explore 30 holiday rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at $60 AUD per night before taxes and fees

  • Verified guest reviews

    Over 550 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Chester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Chester rentals

  • 4.8 Average rating

    Chester stays are highly rated by guests—averaging 4.8 out of 5!

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