
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.

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!

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.

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!

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!

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.

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!

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

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!

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.

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!

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.

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
House rentals with a pool

Spacious and Cozy Oasis on Monument Avenue

The Get-Together

Historic Blanton Getaway

A house you wish you called home

Historic Marshall House 11 plus beds

The Resort

Richmond Home with Pool, 5 Mi to Downtown!
Weekly house rentals

City Point Cottage

Spacious home near downtown RVA

2-Bedroom oasis in Chesterfield

Pennwood Place - The Place to Stay!

Charming Retreat w/ Pool Table in Chesterfield!

The Duck Blind located near RIC airport

Charming, Private Abode: Serenity in Hopewell, VA!

Cozy Sweet Home!
Private house rentals

Historic retreat City Point - walk to river

Pet-Friendly in Petersburg, VA

The Plum Street Double House

Petersburg Vacation Gem 3BR | Private Backyard

Nala's Place

Blue Belle in Historic Church Hill

A Historic Petersburg Home

Brand-New Boho Family Getaway!
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ268 | ﺩ.ﺇ294 | ﺩ.ﺇ191 | ﺩ.ﺇ264 | ﺩ.ﺇ294 | ﺩ.ﺇ331 | ﺩ.ﺇ198 | ﺩ.ﺇ191 | ﺩ.ﺇ176 | ﺩ.ﺇ213 | ﺩ.ﺇ187 | ﺩ.ﺇ275 |
| Avg. temp | 4°C | 5°C | 9°C | 15°C | 19°C | 24°C | 26°C | 25°C | 22°C | 16°C | 10°C | 5°C |
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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