Holiday houses 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.
Guesthouse 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
Guesthouse in Chesterfield
4.99 out of 5 average rating, 72 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
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
An enclosed pool area features a turquoise swimming pool, surrounded by large glass panels that provide views of the outdoor landscape. Two blue lounge chairs are positioned near the pool, creating a calming space for relaxation.
Farm stay in Chesterfield
4.97 out of 5 average rating, 114 reviews

Keystone Acres Farm *Enclosed Heated Pool*

Keystone Acres is located in Chesterfield, VA at a beautiful 1000 acre horse farm. On property we have roughly 60 horses owned by different tenants. The brick farm house in which you will be staying in overlooks one of our ponds & multiple horse barns. We have many "internal" roads here and hope you enjoy the farm views. Our 5 bedroom house is perfect for families or friends who want to have a getaway to "unplug" and experience the country life and each other's time.

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.
Apartment 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.
Guesthouse 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 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.

Guest favourite
The spacious studio features a queen-sized bed adorned with yellow accents, surrounded by lush greenery. Natural light streams through multiple windows, illuminating modern furnishings, including a kitchenette and a coffee station. A cozy rug lies below, enhancing the inviting atmosphere of the room.
Guesthouse in Richmond
4.96 out of 5 average rating, 292 reviews

Funky & colorful private guesthouse with parking!

This unique place has a style all its own with carefully curated touches of yellow! A private guesthouse tucked away and at the top of a spiral staircase. This space is a five minute drive from Richmond's most popular neighborhoods. Fully equipped with a mid-century modern kitchenette, private patio, and A/C! This space is an experience in itself. Explore Richmond's best kept secret; the Yellow Tiger's Den.

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, 161 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
A modern dining area features a wooden table surrounded by four black chairs, complemented by decorative placemats. A potted plant sits centrally on the table. The wall displays a collection of framed artwork, adding character and a local artistic touch to the space.
Home in Richmond
4.87 out of 5 average rating, 239 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!

Guest favourite
The entrance of a historic brick home is graced by a white wooden staircase leading to a dark door. A decorative awning featuring red, white, and blue patterns drapes above the door, with planters positioned on either side. Flanking windows allow natural light to enter.
Home in Petersburgh
4.95 out of 5 average rating, 107 reviews

Historic Home Near Old Town

Private 1850's Greek Revival Home in Historic Petersburg! -Minutes away from Old Town restaurants and shopping -One block from Poplar Lawn Park -Fast wifi, dual zone central ac/heat -Newly renovated first and second floor -Sleeps up to three (couple + one or two singles) *Please read full listing before booking as not everyone will feel comfortable in our lower income neighborhood.

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.
Guesthouse in Richmond
4.97 out of 5 average rating, 467 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!

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