Holiday rentals in Chesterfield County

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.

Private guest apt on creek w/ patio & fire feature

“The Nest” is a private, ground level “basement” apartment. 15 min from downtown Richmond & 18 min to Pocahontas State Park, this space offers a peaceful, conveniently located, retreat. Private entrance, cozy patio, & large yard- all creek side. Laundry, high speed internet, Smart TV. Yard is wooded and private. Restaurants and tons of shopping within 5 min of the house, and 2.5 miles from highway access. A friend rents the upstairs of the home, which is completely separate- no shared space.

The Henry Lofts Unit 1 - 'Chloros Lux Collection'

The Henry Lofts studio provides style, convenience, exposed brick & an open floor plan with 800 sq. ft. You will find a fully fenced pet friendly yard to go along with your private parking, & accommodated apartment with all new everything. This historic building was built in the 1800's but completely renovated with all new appliances and systems in 2024! Walk to all of the local breweries, restaurants, museums, galleries, and boutiques in downtown Old Towne Petersburg, VA. Private Deck/Patio

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

Top Location Cozy Stay - Near Richmond

Discover this brand-new, stylish home designed for comfort and privacy near Richmond. With 5-star guest experiences, this space offers 3 spacious bedrooms, 2.5 modern bathrooms, and a main-level master suite with a remote-controlled reclining bed. Enjoy a bright living area with a large TV, a fully equipped kitchen with island, dining space, private rear porch, garage, driveway, and in-unit laundry. Perfect for families, professionals, or extended stays. Note: Basement has no shared access.

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.

Funky, Private Guesthouse Near Richmond Food Scene

Welcome to the Yellow Tiger’s Den, a private, tucked-away guesthouse filled with bold color, thoughtful design, and a little Richmond edge. Set above a spiral staircase for total privacy, this sunny studio blends mid-century modern style with curated yellow accents, a cozy private patio, and everything you need for a relaxed stay. Located in Richmond’s historic Battery Park neighborhood, you’re minutes from the city’s growing food scene, local attractions, and easy highway access.

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!

Spacious home near downtown RVA

Discover comfort and convenience in our centrally located Airbnb nestled in the heart of the greater Richmond area. Perfectly situated within walking distance to a serene park and soccer fields, it's an ideal retreat for nature lovers and sports enthusiasts alike. Plus, we warmly welcome your furry friends, as our dog-friendly abode boasts a secure fenced backyard for their enjoyment. Book your stay now and experience the best of Richmond's charm and hospitality!

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!

Pink Door-Chesterfield Va

Escape to a soothing 4-bedroom house in Chesterfield. This amazing property features 1 king bed, 3 twin beds, and 2 full beds, ensuring superb comfort for all guests. With WiFi, a washing machine and drying machine, iron, hair dryer, AC, and heating available, your stay will be convenient and stress-free. Fully equipped kitchen for cooking. We hope you enjoy what our place and Chesterfield has to offer.