
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.

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!

Serene Backyard | Dog Friendly | Gazebo | EV
Welcome to Casa Terra, your serene urban retreat, perfect for families & furry companions. Tucked away on a sprawling fenced lot, this property is a rare gem. Let your dogs run free in the 6-ft fenced yard 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.

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

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!

Historical Fan District Home | Walkable & Clean
✨ A beautifully restored home in Richmond’s most iconic neighborhood! Step into historic charm and modern luxury in this fully renovated Fan District home. Whether you're planning a group trip, couples’ retreat, or corporate stay, this spacious and stylish home has everything you need for a relaxing and memorable visit. Enjoy an open-concept design, a private deck & patio, and a prime location just steps from Richmond’s best dining, coffee shops, and attractions.

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!

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!

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

Midterm Rental in between Richmond and Wburg.

Beautiful country house with 5 bedrooms 4.5 baths

Historic Blanton Getaway

YOU FOUND IT! Walkable paradise

A house you wish you called home

Historic Marshall House 11 plus beds

The Resort

Waterfront Hidden Gem in VA
Weekly house rentals

Charming Fully Renovated Cape in West End RVA

Pennwood Place - The Place to Stay!

The Cozy Cottage w/ hot tub! 35min to downtown RVA

Charming Retreat w/ Pool Table in Chesterfield!

The Duck Blind located near RIC airport

Modern Comforts, Classic Charm: Neighborhood Gem

Cozy Sweet Home!

Elegant & Spacious Family Home
Private house rentals

City Point Cottage

Nala's Place

Historic home walkable 2 Restaurants & Distillery

RVA Getaway!

Charming, Private Abode: Serenity in Hopewell, VA!

Brand-New Boho Family Getaway!

3 Queen BRs ‼️ 3-car parking | 9 mins to D'town

Recline at Timberline, Family friendly!
Quick stats about house rentals in Chester
Total rentals
20 properties
Nightly prices starting at
€ 17 before taxes and fees
Total number of reviews
430 reviews
Pet-friendly rentals
10 properties allow pets
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Busch Gardens Williamsburg
- Kings Dominion
- Carytown
- Water Country USA
- Kingsmill Resort
- Pocahontas State Park
- Brown's Island
- Jamestown Settlement
- Royal New Kent Golf Club
- Golden Horseshoe Golf Club
- Independence Golf Club
- Kinloch Golf Club
- The Foundry Golf Club
- Hollywood Cemetery
- The Poe Museum
- Libby Hill Park
- Kiskiack Golf Club
- Science Museum of Virginia
- Grand Prix Raceway
- Hermitage Country Club
- The Country Club of Virginia - James River