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.

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Top guest favourite
A comfortable living area features a brown leather sectional couch with a matching armchair and ottoman. A round table sits on a patterned rug, while soft natural light filters through the window blinds. Two framed animal prints adorn the light-colored wall.
Home in Richmond
4.91 out of 5 average rating, 251 reviews

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!

Top guest favourite
Guest house in Chesterfield
4.98 out of 5 average rating, 99 reviews

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.

Top guest favourite
The private bedroom is accessed through a stylish door featuring the number 203. Inside, a queen-size bed is positioned against a large window with floor-to-ceiling curtains. A contemporary wardrobe is placed nearby, and a textured rug complements the wooden flooring.
Flat in Richmond
4.98 out of 5 average rating, 360 reviews

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.

Top guest favourite
Guest suite in Richmond
5 out of 5 average rating, 78 reviews

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.

Top guest favourite
A living area features a leather sofa and two light-colored accent chairs surrounding a circular glass table. A decorative blue rug anchors the space, while a wall clock adds functionality. The background reveals an open kitchen area, enhancing the suite's spacious feel.
Guest suite in Midlothian
4.97 out of 5 average rating, 178 reviews

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.

Top guest favourite
Tiny home in Richmond
4.99 out of 5 average rating, 203 reviews

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!

Top guest favourite
A welcoming living room features a comfortable sectional sofa and two stylish armchairs arranged around a round coffee table. A TV is mounted above a white mantel, with a decorative plant and wall art enhancing the space. Natural light streams through large windows, illuminating the rich hardwood floors.
Home in Richmond
4.97 out of 5 average rating, 181 reviews

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!

Top guest favourite
Home in Richmond
5 out of 5 average rating, 63 reviews

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!

Top guest favourite
Guest house in Chesterfield
4.95 out of 5 average rating, 320 reviews

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.

Superhost
Home in Richmond
New place to stay

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.

Guest favourite
A spacious exterior view of a modern two-story home is presented, featuring a large, brown garage door and an inviting entryway with steps leading to the front door. The surrounding area includes a gravel driveway and a grassy yard, framed by trees in the background.
Guest house in Chesterfield
4.9 out of 5 average rating, 29 reviews

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.

Guest favourite
Home in Chester
4.92 out of 5 average rating, 95 reviews

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.

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