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, 254 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
4.94 out of 5 average rating, 194 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, 220 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
4.84 out of 5 average rating, 445 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 spacious bedroom is highlighted by a four-poster bed adorned with crisp white linens. Various green plants are positioned around the room, bringing a touch of nature indoors. Soft lighting creates a serene ambiance, with light flooding in through the large windows.
Home in Jackson Ward
4.93 out of 5 average rating, 517 reviews

RVA DownTown/Arts District Clean & Green w/ PARK

Private historic home in center of Arts District! **Extensive Covid Sanitation** This home supports equal rights for all. Discrimination not tolerated. Enjoy your privacy while maintaining the perfect proximity to everything you need! 2 blocks off interstate. High-speed internet/netflix. KING TEMPURPEDIC bed w/ lots of natural light! PLAYGROUND across St. Eco-friendly, all organic white cotton linens. WALK SCORE: 95 (coffee, food, drinks, music, theatre, events) TRAVEL NURSE 10 blocks from MCV.

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, 126 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 favourite
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, 228 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 favourite
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, 109 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

Guest favourite
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
4.83 out of 5 average rating, 150 reviews

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.

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, 141 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, 173 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
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
4.93 out of 5 average rating, 106 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.

Popular amenities for house rentals in Chester

When is the best time to visit Chester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$95 SGD$104 SGD$68 SGD$94 SGD$104 SGD$118 SGD$71 SGD$68 SGD$63 SGD$76 SGD$67 SGD$98 SGD
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Quick stats about house rentals in Chester

  • Total holiday rentals

    Explore 20 holiday rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 430 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Wifi availability

    20 of Chester holiday rentals include wifi 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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