House holiday rentals in Chester

4.94 out of 5 average rating, 209 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.

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.

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!

4.82 out of 5 average rating, 455 reviews

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

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!

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.

4.98 out of 5 average rating, 136 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.

4.98 out of 5 average rating, 255 reviews

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

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!

4.82 out of 5 average rating, 158 reviews

A spacious dining area features a large table surrounded by six elegantly designed chairs with soft cushions. A decorative plant adds a touch of greenery, while the ceiling displays a modern light fixture. The walls are painted in a soft yellow tone, enhancing the warm atmosphere.

Home in Hopewell

Refresh, cheerful home from home.

Relax with the whole family at this peaceful place to stay. A home you surely call home . Newly renovated, professionally decorated to give you the feeling of calmness and enjoyment. Located in the heart of the Tri-cities, near Fort Lee, Southpark Shopping Center, Hopewell marina, the Crossing Shopping Center, convenient store, fast food, gas stations movie theater are minutes away. The house has spacious front, back and left side views with no adjacent neighbors on these three sides.

4.97 out of 5 average rating, 101 reviews

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

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.

4.98 out of 5 average rating, 147 reviews

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

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!

4.93 out of 5 average rating, 179 reviews

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

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!

A living room features a comfortable gray sofa adorned with yellow and black cushions, complemented by a bright yellow chair. A large window allows natural light to flood the space, and a wall-mounted television is positioned above a dark wooden coffee table. Cheerful yellow curtains frame the window.

4.8 out of 5 average rating, 162 reviews

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!

An open dining area featuring a wooden table set with dishes and glasses. A light, floral wallpaper decorates one wall, while a cozy living room with a sofa and coffee table is visible through an archway, enhancing the inviting atmosphere.

4.88 out of 5 average rating, 249 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!

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.

4.95 out of 5 average rating, 111 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 house rentals in Chester

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 65 reviews

Spacious and Cozy Oasis on Monument Avenue

A kitchen space featuring light gray cabinets and a granite countertop. Stainless steel appliances, including an oven and microwave, are visible. A ceiling fan adds to the ambiance, while a decorative backsplash enhances the design. Ample cabinetry provides storage options.

Home in Midlothian

4.52 out of 5 average rating, 25 reviews

The Get-Together

4.98 out of 5 average rating, 45 reviews

The exterior of a historic home is showcased, featuring a welcoming porch adorned with columns. Lush greenery surrounds the property, complemented by a manicured yard. Large windows provide a glimpse into the inviting interior, while the façade reflects a blend of classic architectural details.

Home in Byrd Park

Historic Blanton Getaway

New place to stay

Central Richmond Home

5 out of 5 average rating, 10 reviews

A two-story home features a muted exterior with light grey siding and black shutters. The front porch is accessible via a set of white steps, flanked by neatly trimmed shrubs. A driveway leads to a dark garage, surrounded by a grassy lawn and mature trees.

Home in Midlothian

A house you wish you called home

The exterior of a blue house is showcased, featuring a well-maintained landscape with shrubs and a walkway. A stone border is visible in the foreground, leading to the entrance. Large windows allow natural light into the home, contributing to its welcoming appearance.

5 out of 5 average rating, 28 reviews

The Resort

An open living space features a bright kitchen island with two red bar stools. The area is complemented by a cozy seating arrangement, a dining table, and a fireplace. Large windows allow natural light to fill the room, enhancing the welcoming atmosphere.

4.57 out of 5 average rating, 42 reviews

Richmond Home with Pool, 5 Mi to Downtown!

Weekly house rentals

4.98 out of 5 average rating, 131 reviews

A modern living area features a flat-screen television mounted above a white fireplace, flanked by two vibrant abstract art pieces. The light gray walls enhance the room's spaciousness, while a neutral area rug adds warmth to the hardwood floor.

Home in The Fan

Luxury home in the historic Fan District

A modern gray house is nestled among trees, showcasing a well-manicured lawn. The front features a welcoming entrance with stairs leading to the door, and a spacious two-car garage is visible. Sunlight casts a gentle glow on the clean driveway.

4.89 out of 5 average rating, 45 reviews

Spacious home near downtown RVA

5 out of 5 average rating, 29 reviews

A spacious living room is highlighted by a large purple sectional sofa and a circular coffee table at the center. A flat-screen television is mounted on the wall, and natural light enters from nearby windows. A staircase leads to the upper floor, visible in the background.

Home in Chesterfield

Pennwood Place - The Place to Stay!

A cozy sleeping area features a stylish bed with a gentle tufted design, accompanied by a matching upholstered bench at its foot. Natural light enters through the window, illuminating the warm yellow walls and a decorative mirror positioned nearby.

4.96 out of 5 average rating, 28 reviews

2-Bedroom oasis in Chesterfield

5 out of 5 average rating, 20 reviews

The ranch-style home features a welcoming front porch with white railings, surrounded by well-maintained shrubs and flowering trees. A neatly paved walkway leads to the entrance, while the grassy front yard adds to the property's charm in a friendly neighborhood setting.

Home in Hopewell

Oaklawn Evergreen Rancher

4.89 out of 5 average rating, 61 reviews

A well-appointed bedroom features a spacious bed with layered bedding and decorative pillows. Natural light streams through two windows, complemented by light curtains. A small desk with a chair is positioned beside the bed, offering a dedicated workspace. A light fixture adds warmth to the room.

Home in Hopewell

Charming, Private Abode: Serenity in Hopewell, VA!

4.98 out of 5 average rating, 86 reviews

A quaint tiny house is presented on stilts, showcasing a colorful exterior with a patchwork of red and green panels. A flight of wooden stairs leads to the front door, framed by two small shrubs on either side. An open yard stretches around the house, surrounded by trees.

Home in Quinton

The Duck Blind located near RIC airport

The open living area features warm wood flooring, exposed brick walls, and a cozy seating arrangement. A traditional area rug lies across the floor, with a fireplace visible in the background. A dining area with wooden chairs and a kitchen can be seen, enhancing the inviting space.

4.93 out of 5 average rating, 90 reviews

1830's House in Historic Old Towne Petersburg, VA

Private house rentals

4.84 out of 5 average rating, 38 reviews

A welcoming hallway is highlighted by a stylish archway leading to the entry door. A sleek table with a decorative item is positioned against the wall. In the background, the fully equipped kitchen is visible, featuring modern appliances and light cabinetry. Greenery adds a touch of freshness.

Home in Brookland Park

Charming Northside Retreat

A prominent house sign is attached to a brick wall, featuring the text '704 Double House Spencer'. The sign is framed in a decorative shape, contrasting with the rustic texture of the surrounding red brick.

5 out of 5 average rating, 16 reviews

The Plum Street Double House

4.97 out of 5 average rating, 67 reviews

A spacious living area features a warm color palette with an orange accent wall. Two couches, one yellow and one orange, frame a small coffee table, while a ceiling fan hangs above. A circular mirror decorates the wall, and a kitchen is visible in the background.

Home in Midlothian

Comfort1 Escape

A large two-story house with a welcoming front porch features multiple columns and a symmetrical design. The property is surrounded by trees and a grassy yard, providing a sense of space. Multiple windows on the upper and lower levels allow for ample natural light.

4.83 out of 5 average rating, 70 reviews

Nala's Place

4.89 out of 5 average rating, 27 reviews

A spacious living area features a light-colored sofa and a round coffee table on a textured rug. A dining table with four chairs is visible in the background, accompanied by multiple windows that allow natural light to illuminate the hardwood floors.

Home in Mechanicsville

Room to Relax

5 out of 5 average rating, 16 reviews

The living area features a warm leather sofa and two accent chairs positioned around a wooden coffee table. A colorful area rug adds vibrancy, while a white kitchen area with modern appliances is visible in the background, complemented by greenery and decorative artwork.

Home in Henrico

Parkside Getaway

4.85 out of 5 average rating, 26 reviews

A cozy living room features a sectional sofa with decorative cushions, including a red heart pillow. Two glass coffee tables sit on a light area rug, while ceiling fan blades and wide windows with sheer curtains provide a bright and comfortable atmosphere.

Home in Chesterfield

Charming Retreat w/ Pool Table in Chesterfield!

A newly constructed two-story home is set among lush greenery. The exterior features a blue siding with white accents. A covered front porch is visible, as well as multiple windows allowing natural light. The driveway leads to a gravel path, enhancing the tranquil outdoor environment.