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.

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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, 262 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 favorite
Home in Richmond
4.95 out of 5 average rating, 201 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 favorite
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, 224 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
4.83 out of 5 average rating, 451 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 favorite
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, 132 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.

Top guest favorite
A charming Arts and Crafts bungalow is showcased, featuring a wide front porch supported by green columns. Steps lead up to the entrance, surrounded by well-maintained greenery. The red brick exterior highlights the architectural details, complemented by neighboring homes in a serene neighborhood setting.
Home in Bellevue
4.98 out of 5 average rating, 243 reviews

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!

Top guest favorite
An outdoor hot tub is situated next to wooden steps in a yard adorned with autumn leaves. Surrounding trees display vibrant red foliage, while the house stands to the side, illuminated by soft afternoon sunlight.
Home in Huguenot
4.99 out of 5 average rating, 117 reviews

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

Top guest favorite
The front exterior of a charming row house is showcased, featuring a brick facade with large windows enhancing natural light. A covered porch is adorned with potted plants and a welcoming blue door, inviting guests to enter.
Home in Carytown
4.97 out of 5 average rating, 174 reviews

Entire Historic Row House • Carytown & Museums

The Maker's Den is a charming row house in the best location. Walk 2 blocks to Carytown for unique boutiques & restaurants or head the opposite direction and visit the Virginia Museum of Fine Arts. The house is decorated with artwork from local artists and many pieces are available for purchase during your visit. You will be minutes from Maymont; lush gardens, Nature Center, historic home, and Children's Farm. Walk, bike, or drive to 30+ breweries in Scott's Addition. Experience RVA!

Guest favorite
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 favorite
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, 144 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!

Guest favorite
A spacious bedroom showcases a large bed adorned with greenery-themed bedding. A cozy sitting area is positioned beside a window, allowing natural light to illuminate the room. Floral wallpaper and light-colored furnishings create a serene atmosphere, complemented by soft lighting from bedside lamps.
Home in Midlothian
4.94 out of 5 average rating, 111 reviews

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.

Guest favorite
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, 108 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.

Popular amenities for Chester house rentals

When is the best time to visit Chester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ268ﺩ.ﺇ294ﺩ.ﺇ191ﺩ.ﺇ264ﺩ.ﺇ294ﺩ.ﺇ331ﺩ.ﺇ198ﺩ.ﺇ191ﺩ.ﺇ176ﺩ.ﺇ213ﺩ.ﺇ187ﺩ.ﺇ275
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Quick stats about house rentals in Chester

  • Total vacation rentals

    Explore 20 vacation rentals in Chester

  • Nightly prices starting at

    Chester vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 430 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    20 of Chester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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