Vacation rentals in Chesterfield County

the winter clover.

Forget your worries in this spacious non smoking and serene space. This cozy nest is 1.5hr away from the virginia beach, 9min from Pocahontas state park and 30min from downtown Richmond. Guess have access to a coffee machine, toaster, microwave, refrigerator and oven. A queen size bed in the room with queen size air mattress available per request if guess travels with family. Nice walking trail in the community for morning promenade. we require no more than 2 people at all time on the property.

Location · Value · Heating

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.

Value · Location · Heating

Stay Awhile - Private, Large Yard, Easy Travel

Welcome to the Exurbs! Peaceful property, not quite rural, not quite the suburbs. Still close enough to jump on the interstate and get where ever you need to be fairly quicky. This property has a huge fully fenced back yard, with plenty of room to unwind and relax on the front/back porch. Bring your boats and trailers, plenty of room! Interstate 288: 3 min Interstate 95 Interchange: 5 min Defense Supply: 6 min Chester: 10 min Dutch Gap Boat: 13 min RIC Airport: 20 min Fort Gregg: 20 min

Location · Family · Outdoor spaces

The Enchanted Studio w/ Tree-Top Views

Some spaces feel different the moment you walk in. The Enchanted Studio is one of them. Perched on the second floor of a beautifully crafted Richmond home, the Enchanted Studio greets you with a wall of windows and a view that stops you — a rain garden, towering trees, and a creek threading quietly along the property's edge. Thoughtfully designed, this retreat works for however you need it: a quiet escape, a remote work base, or simply a place to decompress in a beautiful setting.

Value · Location · Quiet

Guesthouse at Historic Bon Air Estate

Charming cottage located on the property of the first house built in the heart of historic Bon Air, Va. This inviting guesthouse has everything you need for a relaxing stay, with a full kitchen and bathroom and a loft bedroom area. A large covered porch with swing, a fire pit and access to a gas grill. Great location, just outside of the City. 2026 UPDATE - we have upgraded to a full 12-000 Btu Mini-Split HVAC system so the cottage stays cool in the summer and warm in the winter!

Location · Family · Quiet

Charming Retreat w/ Pool Table in Chesterfield!

Escape to this spacious home in Chesterfield, VA! Relax in a cozy living room with Roku TV or cook in the fully equipped kitchen with island seating and a coffee corner. Enjoy the rec room with a pool table, laundry nook, and extra TV. The master suite features a king bed, plush seating, and attached bathroom, while two additional bedrooms offer comfort and storage. A second bathroom, roomy deck with grill, and large backyard complete the perfect retreat. Book your stay today!

Value · Location · Kitchen

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.

Value · Family · Getting around

Private Eyrie - Gorgeous View!

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.

Location · Value · Cleanliness

Comfortable 1-Bedroom Apartment

This brand-new 1-bedroom, 1-bathroom in-law suite offers the perfect blend of comfort and style. This home is ideal for those who appreciate both functionality and aesthetics. Enjoy easy access to local hiking and biking trails, perfect for outdoor enthusiasts or those who love to explore nature. Within minutes from shopping centers. With its private entrance and modern amenities, this suite provides both convenience and tranquility.

Value · Location · Cleanliness

$ Cozy 1BR 1BA Apartment: Near Fort Gregg-Adams $

Welcome to our newly remodeled private apartment with 2 separate entrances. Enjoy a dedicated workspace, 2 smart TVs with free Roku, and proximity to Fort Gregg Adams, dining, and shopping. Stay secure with keyless entry and exterior cameras. Fully equipped kitchen, off-street parking, and adjustable thermostat included. Rest peacefully with blackout curtains and a Queen-size bed. Welcome to your home away from home!

Location · Value · Check-in

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.

Location · Value · Bathroom

Romantic Treehouse for 2 in Farm (no kids)

Surrounded by trees and peace in our small farm in a neighborhood, this cozy little cabin is made for secluded romantic stays and to enjoy a relaxing and restful night. Not suitable for children. Cabin is 10 X 12" of cuteness with all the amenities you might need to feel comfortable, electricity, heater, Smart TV, wifi, coffee maker, memory foam bed, and an awesome outdoor bathroom to shower under the stars!

Value · Location · Check-in