
Vacation rentals in Chesterfield County
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Top-rated vacation rentals in Chesterfield County
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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!

Serene Backyard | Dog Friendly | Gazebo | EV
Welcome to Casa Terra, your serene urban retreat, perfect for families & furry companions. Tucked away on a sprawling fenced lot, this property is a rare gem. Let your dogs run free in the 6-ft fenced yard 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.

Adorable 1-bedroom guesthouse
Adorable guest house located above the detached garage on same property as the main house. Perfect for traveling healthcare workers needing monthly stay or quick trips for tourists visiting RVA. All basic cookware and toiletries provided. Guests have private entrance, free parking, and contactless check in. 9min to chesterfield town center 10min to westchester commons 10min to Johnston Willis hospital 15min to st. Francis medical center 17 min to Chippenham 20 min to river city sportsplex

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.

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.

Private B&B in Historic Fan
We are looking for people who will enjoy the Historic Fan District of Richmond. The stand alone apartment includes a bedroom, bathroom, and renovated kitchen which has microwave, refrigerator, toaster ,and Keurig coffee machine. For our overnight guests we will provide the ingredients for a delicious breakfast: baked goods butter jams etc., 6 breakfast cereals, , fresh fruit , tea and for Keurig 10 varieties of coffee plus hot chocolate and hot apple cider.

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.

HideawayOasis/VSU/95/FortGreggAdams/FirePT/PoolTBL
Welcome to Our Hidden Oasis! 🌿✨ This cozy retreat is designed with love and thoughtfulness, perfect for small families and intimate connections. Enjoy year-round outdoor fun—roast s’mores by the fire pit, relax on the patio, or challenge friends to a game of pool. Sleep soundly in our comfy beds and wake up refreshed for new adventures. Whether unwinding or making memories, this home is your perfect getaway. We can't wait to host you!

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.

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!

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!
Popular amenities for Chesterfield County vacation rentals
Other great vacation rentals in Chesterfield County

The Carriage House

Historic Forest Hill Charm

! Cozy Cove near Fort Gregg-Adams: Perfect for 2 !

Guesthouse at Historic Bon Air Estate

The Nook in Beautiful Bon Air

Comfortable 1-Bedroom Apartment

The Henry Lofts Unit 1 - 'Chloros Lux Collection'

Cute 1 bdr guest house with hot tub No venue/pet
Destinations to explore
- Rentals with lake access Chesterfield County
- Pet-friendly rentals Chesterfield County
- Rentals with a washer and dryer Chesterfield County
- Rentals with an EV charger Chesterfield County
- Waterfront rentals Chesterfield County
- Rentals with a kayak Chesterfield County
- Private suite rentals Chesterfield County
- Townhouse rentals Chesterfield County
- Smoking-friendly rentals Chesterfield County
- Hotel rentals Chesterfield County
- Rentals with a fireplace Chesterfield County
- Fitness-friendly rentals Chesterfield County
- Rentals with a hot tub Chesterfield County
- Rentals with breakfast Chesterfield County
- Rentals with a fire pit Chesterfield County
- Rentals with a home theater Chesterfield County
- Family-friendly rentals Chesterfield County
- Rentals with a patio Chesterfield County
- Condo rentals Chesterfield County
- Rentals with outdoor seating Chesterfield County
- Apartment rentals Chesterfield County
- Kings Dominion
- Carytown
- Pocahontas State Park
- Brown's Island
- Jamestown Settlement
- Royal New Kent Golf Club
- Independence Golf Club
- The Country Club of Virginia - James River
- Kinloch Golf Club
- The Foundry Golf Club
- Hermitage Country Club
- Hollywood Cemetery
- The Poe Museum
- Libby Hill Park
- Kiskiack Golf Club
- Science Museum of Virginia
- Grand Prix Raceway
- NGCOA Mid-Atlantic