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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, 235 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
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
4.9 out of 5 average rating, 224 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
A cozy living area is presented with a light-colored sofa adorned with yellow cushions. Nearby, a dining table with wooden chairs is set against the wall. A functional kitchen area features teal cabinetry and stainless steel appliances, illuminated by soft overhead lighting.
Flat in Chester
4.97 out of 5 average rating, 31 reviews

Green Door Escape

Forget your worries in this spacious and serene space. Enjoy a comfortable stay with a private entrance, separate from the main house, with parking at your front door. Privacy prevails! A comfortable home away from home. Access to a lush garden. Queen bed, private en-suite bathroom with shower. Fitted kitchen: Induction-stove ( two plate), Air-fry Microwave, Coffee maker, and Refrigerator. Crockery, cutlery, cookware and utensils, provided. Basic cleaning supplies. Linen changed weekly.

Top guest favourite
An outdoor hot tub is situated next to wooden steps in a yard adorned with autumn leaves. Surrounding trees display vibrant red foliage, while the house stands to the side, illuminated by soft afternoon sunlight.
Home in Richmond
4.99 out of 5 average rating, 117 reviews

Hot Tub Oasis, Minutes from Downtown Richmond

Find the best of both worlds here, a tranquil getaway while only 12 minutes from Downtown, Carytown, Scott's Addition, the VMFA, and more. Enjoy the James River by Tubing, Kayaking, Rafting or Swimming, Hiking, Award Winning Restaurants, all within a 5 minute drive. Our home includes amenities such an 8 person hot tub, a pond dock with beautiful views, outdoor fire pit, patio, essential oil bath, and tea/ coffee on us! Our kitchen is stocked with cookware, spices, & dishes. STR-135430-2024 is

Top guest favourite
Guest house in Chesterfield
4.99 out of 5 average rating, 73 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, 159 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
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.
Flat in Chesterfield
4.83 out of 5 average rating, 360 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, 282 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, 111 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 spacious living area features a light-colored wood floor and comfortable seating arrangements, including a reclining sofa and armchair. A dining table with four chairs is positioned near the kitchenette, which includes modern appliances. Natural light enters through a nearby door, creating an inviting space.
Guest suite in Midlothian
4.95 out of 5 average rating, 41 reviews

Cozy Hideaway guest suite

"The Hideaway" is a spacious and cozy, ground level basement guest suite with easy access to everything in Midlothian. This space offers a convenient, private entrance from the driveway, washer/dryer, high speed internet, 65" smart tv with free Peacock, Netflix, Hulu, Disney, ESPN, Max, Discovery Plus, Paramount, Prime Video, to just name a few. Shared access to the fenced in back yard with a grill and firepit.

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
4.92 out of 5 average rating, 163 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.

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