
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!

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

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.

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!

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!

Petersburg Home away from Home
Brick rancher with Tv/xfinity flex, wifi, ring camera system/new kitchen/bathroom, totally remodeled stainless steel refrigerator, stove, microwave, and dishwasher. Central heat and AC with ceiling fans in every room. Laundry room for your convenience that leads out to a screened porch and fenced in backyard. Six miles from Fort Gregg-Adams Military Base. Four miles from Virginia State University. Seven miles from Virginia Motorsports Park.

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

Spacious and Cozy Oasis on Monument Avenue

The Get-Together

Historic Blanton Getaway

Central Richmond Home

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

Pet-Friendly in Petersburg, VA

Spacious home near downtown RVA

Pennwood Place - The Place to Stay!

Nala's Place

Charming Retreat w/ Pool Table in Chesterfield!

Brand-New Boho Family Getaway!

The Duck Blind located near RIC airport

Charming, Private Abode: Serenity in Hopewell, VA!
Private house rentals

City Point Cottage

Charming Euclid Avenue Escape

Charming and Spacious Cottage in Quiet Community

Carytown Retreat/Pet Friendly & Gourmet Kitchen

Byrd Park Dreamhouse with Backyard Oasis

Near Airport: Cozy Stay w/ Lit Deck & Fast Wi-Fi

Pensacola

Charming Bungalow in the Heart of Richmond
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 62 | € 68 | € 44 | € 61 | € 68 | € 77 | € 46 | € 44 | € 41 | € 50 | € 44 | € 64 |
| 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 € 17 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
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- Busch Gardens Williamsburg
- Carytown
- Kings Dominion
- 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
- The Foundry Golf Club
- The Poe Museum
- Kinloch Golf Club
- Science Museum of Virginia
- Hollywood Cemetery
- Kiskiack Golf Club
- Grand Prix Raceway




