Holiday rentals in Chesterfield County

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Top-rated holiday rentals in Chesterfield County

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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, 234 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.

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, 157 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.

Top guest favourite
A well-appointed sleeping area features a spacious bed with a light pink quilt, flanked by bedside lamps. A cozy sofa is positioned to one side, while a dresser and mirror are visible across the room. The walls are painted in a soft blue, enhancing the serene ambiance.
Guest suite in Richmond
4.99 out of 5 average rating, 124 reviews

Quaint Studio in Oregon Hill

This quaint studio apartment lies in the heart of historic Oregon Hill. Less than two blocks from the James River nestles this space near VCU, Hollywood Cemetery, Brown's Island and Downtown Richmond. Studio on the Hill invites you to enjoy the best of Richmond with its vibrant arts scene, deep history and unbelievable food scene. Whether you're visiting Richmond for move-in day at VCU or a concert at the Allianz Amphitheatre, we're perfectly situated for your stay!

Top guest favourite
The spacious bedroom features a king-sized bed with a white comforter and decorative throw pillows. Two nightstands with lamps flank the bed, and a piece of beach-themed artwork adorns the wall above. A closet is visible behind, and soft light fills the room.
Flat in Richmond
4.89 out of 5 average rating, 849 reviews

Elegant 1-bdrm, Fan, Carytown, VMFA, Byrd Park

Beautifully decorated 1-bedroom apartment that is walking distance to tons of fun things to enjoy in the Fan. You will have the entire place to yourself including a huge bedroom with king bed &TV, living room with double-high queen air mattress (way comfier than sleep sofa) and TV, bathroom and kitchen with microwave, fridge, stove, washer/dryer, etc. Also has a private lot for off-street parking. 2blocks from Carytown, 3blocks from VMFA, 3blocks from Byrd Park.

Superhost
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, 357 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
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
4.95 out of 5 average rating, 278 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
4.9 out of 5 average rating, 293 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
A spacious bedroom showcases a large bed adorned with greenery-themed bedding. A cozy sitting area is positioned beside a window, allowing natural light to illuminate the room. Floral wallpaper and light-colored furnishings create a serene atmosphere, complemented by soft lighting from bedside lamps.
Home in Midlothian
4.94 out of 5 average rating, 109 reviews

The Greenhouse 'n the Heart of Midlothian, VA

The Greenhouse is a whimsical refuge located in the very heart of Old Midlothian Village with its old churches and historic houses and is within a 15-20 minute walking distance from several restaurants. You will love staying in our nature inspired home with its resort inspired furnishings; green, leafy décor, fully equipped kitchen, large bathrooms, stocked laundry room, and large yard with gas grill, picnic table and fire pit.

Top guest favourite
A compact kitchen is featured with a gas stove and ample counter space, complemented by natural wood cabinetry. A stylish patterned wall adds character, while large windows allow for natural light to fill the area. The sleeping area is visible in the background, adding to the cozy ambiance.
Bus in Chesterfield
4.93 out of 5 average rating, 160 reviews

The Creekside Cool Bus

Experience the ultimate glamping adventure in our converted school bus! Nestled on 5 acres of land, the campsite features lush woods and a creek. Enjoy the peace and quiet of nature with the comfort of a home away from home. Our skoolie is the perfect basecamp for outdoor adventures-just 30 minutes to Richmond and 5 minutes from the nearest trailhead at Pocahontas State Park with pass included.

Superhost
An open dining area featuring a wooden table set with dishes and glasses. A light, floral wallpaper decorates one wall, while a cozy living room with a sofa and coffee table is visible through an archway, enhancing the inviting atmosphere.
Home in Richmond
4.87 out of 5 average rating, 237 reviews

GALLERIA SOUTH minutes away from Downtown RVA!

Welcome to our stylish Galleria inspired home, in South Side Richmond VA. You will experience a true essence of local artists and how they inspire our community! Galleria South is centrally located for everything in Richmond Virginia. We are only 5 minutes away from the James River and Forest Hill. And located about 10 minutes from Church Hill, Downtown, Carytown, The Fan, & Museum District!

Top guest favourite
A screened-in porch features comfortable seating and ample natural light. Light-colored chairs with floral patterns are set around a glass table. The porch offers a view of the outdoor surroundings, blending relaxation with nature while providing a sheltered space.
Guest house in Richmond
4.97 out of 5 average rating, 466 reviews

A Place of Peace

A separate cozy cottage for two. Queen sized bed with en-suite full bathroom, plus a screened-in porch and an outside deck. JD, our short-haired orange cat and Ambassador, will be happy to keep you company and share HIS porch!. We are a short drive downtown and a 5-minute walk to the James River. Richmond is a foodie town with great brew-pubs everywhere. All are welcome!

Superhost
A living area is highlighted by an orange sofa with decorative pillows, positioned against a warm orange wall. A television is mounted above, displaying a colorful screen. Natural light enters through two windows adorned with blinds, enhancing the space's relaxed atmosphere.
Guest house in North Chesterfield
4.8 out of 5 average rating, 321 reviews

Modern Studio Guesthouse w/free parking

"Tidings" is a completely private detached unit, 3 minutes from Midlothian Turnpike. This space offers a quiet, convenient, and private entrance with high-speed internet, large yard, quiet neighborhood, convenient to major stores. Many restaurants and tons of shopping within 5 miles!

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