
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.

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.

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.

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!

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!

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.

Sweet Little Home 2
This sweet place with 1 queen & 1 full size bed nestled near to center of the city Richmond and James River Park system. Convenient commute to major employers, downtown, the University of Richmond and VCU as well as Chippenham & VCU hospitals !
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

The Resort

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

City Point Cottage

Petersburg Vacation Gem 3BR | Private Backyard

Pennwood Place - The Place to Stay!

RVA Getaway!

The Duck Blind located near RIC airport

Brand-New Boho Family Getaway!

Richmond Retreat near Airport & City - 3Br/1.5Bth

3 Queen BRs‼️ 3-car park | Dog delight large yard
Private house rentals

Charming Euclid Avenue Escape

Historic retreat City Point - walk to river

Nala's Place

Parkside Getaway

A Historic Petersburg Home

The Cozy House

Elegant & Spacious Family Home

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 | $130 NZD | $143 NZD | $93 NZD | $128 NZD | $143 NZD | $160 NZD | $96 NZD | $93 NZD | $86 NZD | $103 NZD | $91 NZD | $134 NZD |
| 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 $36 NZD per night before taxes and fees

Verified guest reviews
Over 430 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Wi-Fi availability
20 of Chester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Kings Dominion
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- 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




