
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.

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

*Mid-Century Boho* 2 Primary Suites! Private Patio
Welcome to this adorable mid-century modern, boho themed home! 1940s historic charmer! There’s 2 primary suites with private baths. 4 bedrooms total: 2 king beds and 2 queens: all gel memory foam and each room has a smart tv! Come hang out in the private, shaded backyard or the breezy screened in porch! 5 min to the very popular Forest Hill Park & James River. 10 min to Downtown, Carytown, The Fan, Museum District, Church Hill, breweries - great proximity to everything Richmond has to offer!

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 Cottage in the City -Private Yard and Fire Pit
Your family will be close to everything when you stay at this peaceful, centrally-located home. This home is equipped with anything you may need during your stay! Enjoy the beautiful naturally lit living room throughout the day, or stargaze in the back yard while enjoying gentle heat from the firepit. The best part? We are a quick drive to anything you may be looking to do in Richmond and only 12 minutes to downtown center city.

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.

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!
Popular amenities for Chester house rentals
House rentals with a pool

Spacious and Cozy Oasis on Monument Avenue

The Get-Together

Historic Blanton Getaway

YOU FOUND IT! Walkable paradise

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

Historic retreat City Point - walk to river

Spacious home near downtown RVA

2-Bedroom oasis in Chesterfield

Pennwood Place - The Place to Stay!

Charming Retreat w/ Pool Table in Chesterfield!

Charming, Private Abode: Serenity in Hopewell, VA!

The Duck Blind located near RIC airport
Private house rentals

The Plum Street Double House

Nala's Place

Blue Belle in Historic Church Hill

A Historic Petersburg Home

RVA Getaway!

The Cozy House

Brand-New Boho Family Getaway!

Elegant & Spacious Family Home
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$15,274 GYD | G$16,739 GYD | G$10,880 GYD | G$15,065 GYD | G$16,739 GYD | G$18,831 GYD | G$11,299 GYD | G$10,880 GYD | G$10,043 GYD | G$12,135 GYD | G$10,671 GYD | G$15,692 GYD |
| 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 G$4,185 GYD 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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- Busch Gardens Williamsburg
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- Kings Dominion
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- Pocahontas State Park
- Jamestown Settlement
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- Royal New Kent Golf Club
- Golden Horseshoe Golf Club
- Independence Golf Club
- Libby Hill Park
- The Country Club of Virginia - James River
- The Foundry Golf Club
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- Hermitage Country Club
- The Poe Museum
- Science Museum of Virginia
- Hollywood Cemetery
- Kiskiack Golf Club
- Grand Prix Raceway




