
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.

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.

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!

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.

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.

Cheerful high ceiling studio in walkable Fan Dist
Super cool first floor studio apartment nestled in RVA's pedestrian-friendly Fan District. You'll be steps away from bars, restaurants, and art galleries in this "very Richmond" location. Built in 1900, the space has impressive features including a huge bay window overlooking lively W Main St and two (non functional) fireplaces. Velvety curtains divide the bedroom/living area from the eat-in kitchen. Lovely high ceilings. Art and furnishings give cottage in the city vibes.

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.

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.

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.

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.

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.

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.

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.
Popular amenities for Chesterfield County holiday rentals
Other great holiday rentals in Chesterfield County

Charming Hopewell Gem: Game Room & Prime Location

1BR Apt - Stonewall Manor at Keystone

3 BR/2 Bth house mins from three local hospitals

Shared home w/private bed & bath in N. Churchill

Travel and Explore, enjoy this home with Heart

Qualla Park

Peaceful - 9 mins to D'town/VCU

The Enchanted Studio
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- Carytown
- Kings Dominion
- Pocahontas State Park
- Jamestown Settlement
- Brown's Island
- Libby Hill Park
- Science Museum of Virginia
- The Poe Museum
- Hollywood Cemetery
- Greater Richmond Convention Center
- Altria Theater
- Forest Hill Park
- Virginia Holocaust Museum
- Children's Museum of Richmond
- Colonial Williamsburg's Merchants Square
- American Civil War Museum
- Virginia State Capitol-Northwest
- The National
- Things to do Chesterfield County
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