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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 wooden dock extends over the calm water, featuring a round table surrounded by four blue chairs. A swinging hammock chair hangs nearby, with an American flag gently waving. String lights are suspended overhead, adding a touch of ambiance to the scenery.
Guest house in Church Road
5 out of 5 average rating, 239 reviews

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.

Guest favourite
Flat in Richmond
4.9 out of 5 average rating, 285 reviews

Gem of Fan district/Private Parking/Fenced/2 TVs

This beautiful historic home was built in 1902 and offers a perfect blend of contemporary design, traditional architecture, and modern amenities. Just a block away from Monument Avenue, you will find yourself close to many fabulous restaurants, coffee shops, bakeries, markets, and gift shops. * Newly renovated in 2022 *Peaceful fully fenced backyard *0ne dedicated parking space *Minutes from everything *Pet friendly *Fully equipped kitchen with new appliances *New washer and dryer in-unit

Guest favourite
Guest house in Richmond
4.96 out of 5 average rating, 302 reviews

Funky, Private Guesthouse Near Richmond Food Scene

Welcome to the Yellow Tiger’s Den, a private, tucked-away guesthouse filled with bold color, thoughtful design, and a little Richmond edge. Set above a spiral staircase for total privacy, this sunny studio blends mid-century modern style with curated yellow accents, a cozy private patio, and everything you need for a relaxed stay. Located in Richmond’s historic Battery Park neighborhood, you’re minutes from the city’s growing food scene, local attractions, and easy highway access.

Top guest favourite
A spacious wooden deck provides an outdoor retreat, featuring a comfortable hammock and patio heaters along the railing. Lush trees surround the area, offering privacy and a peaceful atmosphere.
Guest suite in Midlothian
4.97 out of 5 average rating, 164 reviews

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.

Guest favourite
Home in Richmond
4.96 out of 5 average rating, 151 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
A modern sitting area features a sleek black sofa with accent cushions, complemented by a wooden coffee table. A collection of framed artwork adorns the light grey wall. A small plant is positioned on a side table next to a stylish lamp, enhancing the minimalist aesthetic.
Flat in Richmond
4.95 out of 5 average rating, 236 reviews

Historic Hill Top Beauty - 2nd Floor

Situated across from beautiful Chimborazo Park, this historic limestone home dates back to 1902. The entire sun flooded top floor features two bedrooms, an eat in kitchen, and a full bathroom. Unit also includes a 56" smart TV and two desk areas if needed. Need to run a load of laundry? No problem there is a ventless all in one washer/dryer. Shared front porch with rockers and park views, and a shared back yard offer additional social distance friendly ways to hang out.

Guest favourite
A cozy living area features a light-colored sofa with decorative pillows, positioned next to a stone fireplace. A wooden dining table is visible, along with a lush green plant. Wall art and decorative plates add character to the space, illuminated by natural light from the window.
Flat in Chesterfield
4.83 out of 5 average rating, 369 reviews

Private guest apt on creek w/ patio & fire feature

“The Nest” is a completely private, ground level “basement” apartment. 15 minutes from downtown Richmond & 18 minutes to Pocahontas State Park, this space offers a peaceful, conveniently located, retreat. Private entrance, cozy patio, & large yard- all creek side and professionally designed. Laundry in unit, high speed internet, Smart TV. Yard is wooded and private. Many restaurants and tons of shopping within 5 min of the house, and 2.5 miles from highway access.

Top guest favourite
The image showcases a historic Victorian home featuring a green exterior with a prominent dome roof. The entrance is framed by a covered porch, and flowering bushes add color to the front garden. Brick pathway leads to the front door, enhancing the inviting appearance.
Flat in Richmond
4.94 out of 5 average rating, 820 reviews

Private B&B in Historic Fan

We are looking for people who will enjoy the Historic Fan District of Richmond. The stand alone apartment includes a bedroom, bathroom, and renovated kitchen which has microwave, refrigerator, toaster ,and Keurig coffee machine. For our overnight guests we will provide the ingredients for a delicious breakfast: baked goods butter jams etc., 6 breakfast cereals, , fresh fruit , tea and for Keurig 10 varieties of coffee plus hot chocolate and hot apple cider.

Top guest favourite
A second floor apartment is viewed from below, featuring a spacious balcony with a railing. Large windows allow natural light to fill the interior, surrounded by lush greenery. The building is designed in a contemporary style with a cozy, elevated appearance.
Guest house in Chesterfield
4.96 out of 5 average rating, 290 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.

Guest favourite
A modern living area features a spiral staircase leading to the upper floor. Natural light filters through skylights and large windows. A mix of furnishings, including a green accent chair, a brown couch, and a glass coffee table, adds to the stylish ambiance.
Apartment in Richmond
4.91 out of 5 average rating, 301 reviews

Sixteen West - Modern Apartment in Richmond

Welcome to Sixteen West! This stylish, modern apartment is nestled in the heart of historic Jackson Ward. Recently renovated, the space features beautiful hardwood flooring, updated lighting fixtures, and a sleek, fully equipped kitchen. You'll be within walking distance of some of Richmond’s best spots, including Tarrant's Café, Quirk Hotel, The National, and more! Please note: This unit requires climbing 2.5 flights of stairs — THERE IS NO ELEVATOR.

Guest favourite
The spacious living area features a green couch, a reclining chair, and a wooden coffee table, arranged on a soft area rug. Light streams in from the high ceiling, highlighting framed plant artwork on the wall and a glimpse of the kitchen in the background.
Flat in Richmond
4.95 out of 5 average rating, 127 reviews

Spacious unit in Arts District

Tucked away in the heart of The Arts District, you'll be able to walk to all the best restaurants and activities the city has to offer. A few blocks away from The National and a few minutes away from Cary Town, The Fan, Shockoe Bottom, Manchester, and Scott's Addition, you'll have easy access to anything the city has to offer! Just blocks away from the convention center, this unit is perfect for Richmond guests who are in town for work related events.

Top guest favourite
A compact kitchen area features wood cabinetry and stainless steel appliances. A granite countertop is complemented by two bar stools, providing seating. A black leather armchair sits nearby, and natural light enters through a window dressed with light curtains.
Flat in Richmond
4.9 out of 5 average rating, 795 reviews

Cozy Museum District Apartment

Our cozy Museum District apartment is our personal escape in Richmond Virginia. This listing is conveniently located to many bars, restaurants, and breweries. We are also easy walking distance from the Virginia Museum of Fine Arts, the Virginia Historical Society, and Black Hand Coffee. You will love our updated kitchen and comfy bed. Our apartment is great for couples, solo adventurers, and business travelers.

Popular amenities for Chesterfield County holiday rentals

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