
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.

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!

Lulu's Peaceful Cottage
Enjoy a relaxing stay at this great located cottage. Lulu's Peaceful cottage is brand new, stylishly decorated for comfort. Private little cottage in a park like setting amongst trees & nature. Inside is an equipped kitchenette, coffee/tea bar, & is meal prep friendly. Relax in the soaking tub, or shower if you prefer. Lulu's is close to everything. Shopping, gyms, parks, & recs, hospitals, museums, & airport, and just a few miles from all major highways. Easy driveway parking & keyless entry.

Stunning Modern Studio Will Take Your Breath Away
In Church Hill, cultures intersect to create one of Richmond, VA's most diverse, hip, and walkable neighborhoods. With picture perfect views of the skyline from Jefferson Park, cuisine from award-winning eateries and local shopping boutiques, Church Hill has something for everyone, is close to everything (10 min from airport, right next to downtown), and delivers a uniquely rich way to experience the Virginia's capital. We’re booking now for staycations, vacations, and all things in between.

The Enchanted Studio w/ Tree-Top Views
Some spaces feel different the moment you walk in. The Enchanted Studio is one of them. Perched on the second floor of a beautifully crafted Richmond home, the Enchanted Studio greets you with a wall of windows and a view that stops you — a rain garden, towering trees, and a creek threading quietly along the property's edge. Thoughtfully designed, this retreat works for however you need it: a quiet escape, a remote work base, or simply a place to decompress in a beautiful setting.

Chateau Midlothian Retreat Suite
The perfect guest suite waiting to great you to relax in this cozy retreat. Full renovation completed in 2023, 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.

The Barkin’ B & B
Just five minutes from the airport and downtown, this cozy tiny home offers rustic charm and modern comfort. Fully equipped with kitchen essentials, books, games, and even coloring books, it’s perfect for relaxing. Pet-friendly, it comes stocked with dog treats, chews, toys, and a large fenced-in backyard for furry companions to enjoy. Conveniently located for travelers, it provides a peaceful retreat while keeping you close to city attractions. A perfect home away from home!

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!

Backyard & Barbell RVA Retreat
Tranquil, centrally located getaway minutes from the Allianz amphitheater, downtown, and natural scenery. Whether you are looking for a place to unwind and relax or get a solid workout in, we have you covered. We can accommodate up to 4 guests, however, one of the bedrooms was converted into a gym. There is an air mattress and full sheet set (pictured) for additional guests. Your four-legged friends are going to love the backyard, so please feel free to bring them along!

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.

Waterfront Escape | Hot Tub, Canoe & SUP
Welcome to Rushes Reservoir—a waterfront retreat with treetop views hidden in the heart of Richmond. Perched above the reservoir, the home's main living spaces feel suspended in the canopy, with sweeping views of the woods and water. Relax in the hot tub, gather around the fire pit, paddle the reservoir by canoe or SUP, fish from the dock, or unwind on the expansive deck—all just minutes from Richmond's restaurants, breweries, and attractions.

Comfortable 1-Bedroom Apartment
This brand-new 1-bedroom, 1-bathroom in-law suite offers the perfect blend of comfort and style. This home is ideal for those who appreciate both functionality and aesthetics. Enjoy easy access to local hiking and biking trails, perfect for outdoor enthusiasts or those who love to explore nature. Within minutes from shopping centers. With its private entrance and modern amenities, this suite provides both convenience and tranquility.

Brand new, beautiful home.
This new built home, with 1570 sf , fresh from driveway to kitchen, welcomes you. Come, Relax with the whole family at this brand new elegant, peaceful place to stay. The house is in a quiet, peaceful Chester neighborhood, minutes from Amazon warehouse, Capital One, Lego Land. Cinema Cafe, Fort Greg-Adam, Richmond downtown, Richmond Airport are less than 30’. You’ll love it.
Popular amenities for Chesterfield County holiday rentals
Other great holiday rentals in Chesterfield County

The Birdhouse - Cozy Cottage Retreat in Richmond

Parkside Log Cabin

Pink Door-Chesterfield Va

Cozy & Curated + Backyard Bliss

Charming Retreat w/ Pool Table in Chesterfield!

Top Location Cozy Stay - Near Richmond

Guesthouse at Historic Bon Air Estate

The Henry Lofts Unit 3 - 'The Sunset Suite'
Destinations to explore
- Hotel rooms Chesterfield County
- Rentals with pools Chesterfield County
- Pet-friendly rentals Chesterfield County
- Rentals with a cinema Chesterfield County
- Rentals with an EV charger Chesterfield County
- Rentals with outdoor seating Chesterfield County
- Townhouse rentals Chesterfield County
- Rentals with a kayak Chesterfield County
- Rentals with a firepit Chesterfield County
- Flat rentals Chesterfield County
- Private suite rentals Chesterfield County
- Rentals with a fireplace Chesterfield County
- Smoking-friendly rentals Chesterfield County
- Rentals with a patio Chesterfield County
- Guest house rentals Chesterfield County
- Loft rentals Chesterfield County
- Rentals with breakfast Chesterfield County
- Family-friendly rentals Chesterfield County
- Rentals with a hot tub Chesterfield County
- Serviced apartment rentals Chesterfield County
- Fitness-friendly rentals Chesterfield County
- House rentals Chesterfield County
- Apartment rentals Chesterfield County
- Rentals with lake access Chesterfield County
- Rentals with a washing machine and dryer Chesterfield County
- Kings Dominion
- Pocahontas State Park
- Jamestown Settlement
- Greater Richmond Convention Center
- Brown's Island
- Colonial Williamsburg's Merchants Square
- Libby Hill Park
- The Poe Museum
- The National
- Forest Hill Park
- Virginia Holocaust Museum
- Altria Theater
- Science Museum of Virginia
- Hollywood Cemetery
- Children's Museum of Richmond
- American Civil War Museum
- Virginia State Capitol-Northwest
- Metro Richmond Zoo
- Jefferson Park
- The Diamond
- Things to do Chesterfield County
- Things to do Virginia
- Sightseeing Virginia
- Nature and outdoors Virginia
- Sports activities Virginia
- Art and culture Virginia
- Tours Virginia
- Food and drink Virginia
- Things to do United States
- Tours United States
- Food and drink United States
- Sightseeing United States
- Entertainment United States
- Sports activities United States
- Art and culture United States
- Wellness United States
- Nature and outdoors United States





