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Holiday rentals in Chesterfield County

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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
The image captures a serene sunset over Lake Chesdin, with vibrant hues of orange and purple reflecting on the water's surface. A wooden dock extends into the lake, accompanied by a flag gently fluttering in the breeze. The scene embodies tranquility and natural beauty.
Guest house in Church Road
5 out of 5 average rating, 243 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
Home in Richmond
4.95 out of 5 average rating, 223 reviews

Pet-Friendly Oasis: Sprawling Fenced Yard + 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.

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
4.84 out of 5 average rating, 370 reviews

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.

Top guest favourite
A well-equipped kitchen features wooden cabinetry and a modern design. Stainless steel appliances, including a refrigerator and microwave, complement the white countertops. An island with seating offers additional space, while decorative floral backsplash adds a touch of charm. Natural light brightens the room through nearby windows.
Home in Richmond
5 out of 5 average rating, 21 reviews

Stay Awhile - Private, Large Yard, Easy Travel

Welcome to the Exurbs! Peaceful property, not quite rural, not quite the suburbs. Still close enough to jump on the interstate and get where ever you need to be fairly quicky. This property has a huge fully fenced back yard, with plenty of room to unwind and relax on the front/back porch. Bring your boats and trailers, plenty of room! Interstate 288: 3 min Interstate 95 Interchange: 5 min Defense Supply: 6 min Chester: 10 min Dutch Gap Boat: 13 min RIC Airport: 20 min Fort Gregg: 20 min

Top guest favourite
A single-story home is surrounded by trees, featuring a gravel driveway. A white fence borders a patio area with multiple chairs, which provide an outdoor seating space. The house showcases a covered porch stretching along its front, enhancing the connection to the natural surroundings.
Home in Midlothian
5 out of 5 average rating, 173 reviews

The Cottage on Bernard's Creek

Enjoy the whole house, 3 bedroom, plus junior suite, 2 bath home on 9 acres located on Bernard's Creek. This 2000 sq ft home has been tastefully furnished with updated amenities, and antique furnishings. Seven guests will look forward to experiencing this home that's located in a private setting yet less than 5 minutes to local restaurants and quick access to interstate 288. Guests love the screened porch for relaxing and dining, plus an outdoor fire pit for sunsets and evening gatherings.

Top guest favourite
An open living area features a green sofa and a coffee table, with a modern electric fireplace beneath a wall-mounted TV. A round dining table is set by large windows, while a kitchenette is visible in the background. Light-colored walls enhance the spacious feel.
Guest suite in Richmond
4.99 out of 5 average rating, 159 reviews

River City Oasis - close to river & hiking trails

-City convenience with lots of nature spots close by! -Walk to James River, Forest Hill Park, Buttermilk Trail, Belle Isle, and the Allianz Ampitheatre. -All one level on the 1st floor with private entrance and easy on-street parking -Kitchenette for cooking small meals -Woodland Heights historic neighborhood -Newly built in 2023! -Modern bathroom with heated floor -Blackout curtains for peaceful sleep -Dedicated HVAC that you control -Close to restaurants, coffee shops and local brewery

Guest favourite
The apartment entrance features a black door with the number 212 A prominently displayed. Two gray chairs are positioned on the porch, accompanied by a welcome mat. Windows adjacent to the door allow natural light to brighten the entryway.
Flat in Richmond
4.93 out of 5 average rating, 163 reviews

Manchester gem w/ fenced backyard and parking

Spacious first-floor apartment with 1 king-size and 1 queen-size bedroom. Large fenced-in backyard (rare for this downtown location) along with free off-street parking. Nestled in Old Manchester, this unit is only a couple blocks from the James River and its trail system, Potterfield bridge, coffee shops, and dining. Restaurants and breweries (Legend, Basic, and Benchtop) are within walking distance. Located by three bridges and I-95, you'll find getting around the city very easy.

Superhost
Flat in Richmond
4.84 out of 5 average rating, 174 reviews

The Fan Comfort Stay near VCU Free Parking Fenced

Welcome to your Richmond retreat in the heart of The Fan / VCU district! This cozy and spacious 1-bedroom apartment is perfect for couples, business travelers, or small groups visiting the city. The apartment features a newly renovated bathroom, comfortable living space, fully equipped kitchen, and two free private parking spaces behind the house. Located just minutes from VCU, restaurants, coffee shops, galleries, and downtown Richmond, it’s the perfect base for exploring the city.

Superhost
A well-lit living space features an open layout with a cozy yellow sofa and a decorative area rug. A small table with drinks rests in front of the couch. The kitchen showcases wooden cabinets, stainless steel appliances, and seating at the counter bar.
Home in Richmond
4.84 out of 5 average rating, 246 reviews

Snug in Carver

Right in the heart of Carver, we're just blocks from VCU, the Altria Theater, and Monroe Park. We're also THE closest Airbnb to the interstate in the city of Richmond. If you're getting off 95/64 in the evening, you can slip right back on in the morning in about 90 seconds flat! We're just a hop-skip from downtown and all that has to offer. Stroll down through the First Friday gallery walk, or enjoy all the delicious restaurants and bars Jackson Ward and Broad St. have to offer.

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, 165 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
The cottage is situated on a spacious lawn surrounded by mature trees, with warm light glowing from the windows. A welcoming porch features steps leading to the garden, while the evening sky transitions into twilight, enhancing the serene natural setting.
Guest house in Midlothian
4.86 out of 5 average rating, 29 reviews

The Cottage at Huguenot Springs

Escape to The Cottage at Huguenot Springs, a charming one-bedroom, one-bath retreat nestled on 12 acres of serene, mature grounds just minutes from Richmond, Virginia. Enjoy your morning coffee surrounded by generous lawns and majestic oaks, spot grazing deer at dusk, and unwind in peaceful, natural surroundings. Whether you're seeking relaxation, a bit of history, or easy access to the city, this idyllic cottage offers the perfect balance of nature, privacy, and convenience.

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, 296 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.

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