
Holiday rentals in Chesterfield County
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chesterfield County
Guests agree: these stays are highly rated for location, cleanliness and more.

Heron Rock- Lakefront Cottage on Lake Chesdin
Enjoy peaceful lakefront living at Heron Rock Cottage, where you can stroll through the woods, swim or fish off the dock, paddle the lake in kayaks, or simply relax and enjoy the wildlife and beautiful sunsets. Situated on 6 acres in Dinwiddie County, this newly renovated cottage includes 2 bedrooms, full bath, full kitchen, living room with fireplace and private patio with dining area. Your stay includes full access to the grounds and dock and you are welcome to tie up a boat if you bring one.

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!

Open 2 acre, Huge yard/drive, K, K, Q bed, 2 bath
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.

Private guest apt on creek w/ patio & fire feature
“The Nest” is a private, ground level “basement” apartment. 15 min from downtown Richmond & 18 min to Pocahontas State Park, this space offers a peaceful, conveniently located, retreat. Private entrance, cozy patio, & large yard- all creek side. Laundry, high speed internet, Smart TV. Yard is wooded and private. Restaurants and tons of shopping within 5 min of the house, and 2.5 miles from highway access. A friend rents the upstairs of the home, which is completely separate- no shared space.

Cozy Studio w/ Private Patio in Church Hill
Our dreamy, fully equipped private studio apartment and adjacent garden nestled in the Historic Church Hill neighborhood is an ideal retreat for a couple or solo traveler looking for close proximity to The River City but want a quieter feel. Be at ease with free street parking, fast wifi, an airy interior, outfitted kitchen, and a secluded green terrace. Within a 15 min walk are top-notch restaurants, coffee shops, bakeries, bars, provisions stores, salons, the post office, and four parks.

Dear John
Hospitality has been our life’s work. . The suites by Dear John LLC are executed with the same keen attention to detail as our award winning restaurants. We feature Casper Pillows, Tuft & Needles luxury mattresses and 700 thread count sheets. From black out shades to white noise & everything in between, we’ve got you covered for a restful retreat. A soaking tub & sauna are just a few of the surprises at DJ. Enjoy our chef’s kitchen or pop into one of the fan’s many great eateries.

Chateau Midlothian Retreat Suite
The perfect guest suite waiting to great you to relax in this cozy retreat. Full renovation completed in 2022, including all new furnishings. As an Airbnb traveler, I focused on a clean, comfortable space that guests enjoy and recommend to others. The Chateau Midlothian Suite Retreat is limited to two adult guests with reservations. No other outside guests are permitted. All guests must have their identity verified through Airbnb with at least two reviews to make reservations.

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!

Renovated Modern Home Minutes to Downtown Richmond
Welcome to your bright, peaceful, spacious retreat, while only 15 minutes from Downtown, Carytown, Scott's Addition, the VMFA, and more. And only a 4 minute drive to Trader Joe's! Local hikes, restaurants and Chesterfield mall, all within a 7 minute drive. Your kitchen boasts all brand new appliances and plenty of new cookware. Local sightseeing, brewery & eatery guides provided. *Note: Carbon monoxide alarm not present because the house runs entirely on electric*

Gorgeous 1-Bdrm in the Fan near Carytown & VMFA
My place is 2 blocks from Carytown, 5 blocks from VMFA, 4 blocks from Byrd Park and has 10+ restaurants within 3-5 blocks. 2-3 miles from Browns Island and Belle Island. You’ll love my place because the location is central to everything Richmond, comfortable bed, washer and dryer, cable TV in living room and bedroom + wifi and a queen air mattress for extra sleepers. My place is good for couples, solo adventurers, business travelers, families (with kids)

Gorgeous Creek View from your Private Eyrie
Enjoy a relaxing view of Falling Creek from the second floor apartment with a private entrance and balcony. The wall of windows overlooks a secluded backyard with visiting deer, heron, owls, and other wildlife. Sit by the pond, creek or fire pit. The property offers off street parking in a safe neighborhood which is located 20 minutes from downtown Richmond, 10 mins to Midlothian and Chesterfield, 3 mins to Swim RVA. 15 mins to the airport or train station.

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!
Popular amenities for Chesterfield County holiday rentals
Other great holiday rentals in Chesterfield County

Spacious home near downtown RVA

Farm getaway with Highland Cows and scenic views

Parkside Log Cabin

Pink Door-Chesterfield Va

Spacious 2BR Hidden Gem

The Enchanted Studio

Exquisite Farmhouse Style Home

Luxe King Bd W Resort Amenities, Moseley, VA
Destinations to explore
- Rentals with an EV charger Chesterfield County
- Serviced apartment rentals Chesterfield County
- Rentals with outdoor seating Chesterfield County
- Private suite rentals Chesterfield County
- Rentals with a washing machine and dryer Chesterfield County
- Hotel rooms Chesterfield County
- Flat rentals Chesterfield County
- Rentals with a cinema Chesterfield County
- Loft rentals Chesterfield County
- Fitness-friendly rentals Chesterfield County
- Smoking-friendly rentals Chesterfield County
- Guest house rentals Chesterfield County
- Rentals with a firepit Chesterfield County
- Family-friendly rentals Chesterfield County
- House rentals Chesterfield County
- Rentals with a fireplace Chesterfield County
- Rentals with a hot tub Chesterfield County
- Apartment rentals Chesterfield County
- Pet-friendly rentals Chesterfield County
- Rentals with a patio Chesterfield County
- Rentals with breakfast Chesterfield County
- Rentals with lake access Chesterfield County
- Waterfront rentals Chesterfield County
- Townhouse rentals Chesterfield County
- Rentals with a kayak Chesterfield County
- Rentals with pools Chesterfield County
- Kings Dominion
- Greater Richmond Convention Center
- Pocahontas State Park
- Jamestown Settlement
- Brown's Island
- Libby Hill Park
- Science Museum of Virginia
- The Poe Museum
- Hollywood Cemetery
- Colonial Williamsburg's Merchants Square
- Altria Theater
- The National
- Virginia Holocaust Museum
- Forest Hill Park
- Children's Museum of Richmond
- Virginia State Capitol-Northwest
- American Civil War Museum
- Things to do Chesterfield County
- Things to do Virginia
- Sightseeing Virginia
- Tours Virginia
- Nature and outdoors Virginia
- Art and culture Virginia
- Food and drink Virginia
- Things to do United States
- Sightseeing United States
- Sports activities United States
- Art and culture United States
- Food and drink United States
- Wellness United States
- Nature and outdoors United States
- Entertainment United States
- Tours United States




