
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.

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!

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.

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

Cozy 3-Bedroom Home - Minutes to Downtown Richmond
Your family and friends will love the convenience of this centrally located home, while also enjoying the cheerful and cozy space it offers. It's just minutes from Richmond International Raceway, the Convention Center, VCU campuses, and downtown Richmond, which offers an influx of wonderful restaurants and eateries...both indoor or patio dining. Don't delay...make your reservation today! Your host's top priority is YOU and making sure your stay is a comfortable and enjoyable experience!

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!

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

Rooted Soul Farm-Get rooted, stay soulful.

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

The Resort

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

City Point Cottage

Pennwood Place - The Place to Stay!

Richmond Heartthrob: A Stylish River City Retreat!

The Cottage on Bernard's Creek

Charming Retreat w/ Pool Table in Chesterfield!

The Duck Blind located near RIC airport

Brand-New Boho Family Getaway!

Downtown Fan District free parking* walk to Cary
Private house rentals

Historic retreat City Point - walk to river

Charming and Spacious Cottage in Quiet Community

Nala's Place

RVA Getaway!

Charming, Private Abode: Serenity in Hopewell, VA!

Cozy Sweet Home!

Recline at Timberline, Family friendly!

Near Airport: Cozy Stay w/ Lit Deck & Fast Wi-Fi
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| 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 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!
Destinations to explore
- New York City Holiday rentals
- Western North Carolina Holiday rentals
- Washington Holiday rentals
- Jersey Shore Holiday rentals
- Myrtle Beach Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Jersey City Holiday rentals
- Cape Fear River Holiday rentals
- Busch Gardens Williamsburg
- Kings Dominion
- Carytown
- Water Country USA
- Pocahontas State Park
- Brown's Island
- Jamestown Settlement
- Royal New Kent Golf Club
- Golden Horseshoe Golf Club
- Independence Golf Club
- Libby Hill Park
- Kinloch Golf Club
- The Foundry Golf Club
- The Poe Museum
- Hollywood Cemetery
- Kiskiack Golf Club
- Science Museum of Virginia




