Guest house holiday rentals in Chesterfield County

Private Guesthouse: near Forest Hill Park & River

Experience the best of RVA from a unique stay near it all — a large pet friendly & luxe garage guesthouse with a kitchenette, bathroom, bedroom, lounge, courtyard, & work area. This unit is tucked into Richmond’s beloved Forest Hill and offers full privacy with its own courtyard, alley entrance, & dedicated parking. Stroll or bike to Forest Hill Park for trails, markets, & the riverfront, or wander to neighborhood bakeries, cafés, breweries, & yoga while you stay. Close to Carytown & Maymont.

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.

Heart of the Fan, Monument Avenue Carriage House

Welcome to our sweet little carriage house in the Fan District on historic Monument Ave. Carriage houses are stand-alone buildings from days when people had carriages instead of cars. These lovely old two-story buildings date to the early 1900s, but the indoors here is modernized, offering quiet, elegant privacy in the very center of the bustling Fan. We live in the main house; you will be in back private guesthouse, which you will have for yourself, but we are nearby if anything comes up!

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

Charming Carriage House in Richmond's Fan District

Take a step back in time in your private RVA sanctuary! Located in Richmond's Historic Fan District, this two-story Carriage House is just 2 blocks from the VMFA and countless restaurants, bars, shops and much more. Enjoy the charm of this beautifully-appointed and inviting, 1,000 sq. ft. space with modern amenities, custom art and decor. The open first-floor layout features a lovely living area and renovated, dream bathroom. The upstairs master suite features a king bed and full bath.

Little Sanctuary

Tucked in the peaceful back corner of our property, this cozy tiny guest house offers the perfect escape. With a Murphy bed, reading loft, full kitchen, desk, and a private deck, it has everything you need, including a full bathroom, TV, and internet. Just 15 minutes from downtown Richmond and near the James River and local parks, it's ideal for both city adventures and outdoor exploration. A serene retreat with modern amenities, perfect for a relaxing getaway or productive stay.

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!

Brand New Casita 10 Min to VCU&Downtown w/Parking

Welcome to La Casita Retreat, a newly built private guesthouse near Downtown Richmond, VCU, and VCU Medical Center. Ideal for business travel, university events, healthcare-related stays, or visiting family and friends. Enjoy convenient access to the city while having a comfortable space of your own. Features include a queen bedroom, a queen-size sofa bed in the living area, a full kitchen, dedicated workspace, fast WiFi, in-unit laundry, covered parking, and a private entrance.

The Cottage at Huguenot Springs

Escape to The Cottage at Huguenot Springs, a charming one-bedroom, one-bath retreat nestled on 12 acres of serene, mature grounds just minutes from Richmond, Virginia. Enjoy your morning coffee surrounded by generous lawns and majestic oaks, spot grazing deer at dusk, and unwind in peaceful, natural surroundings. Whether you're seeking relaxation, a bit of history, or easy access to the city, this idyllic cottage offers the perfect balance of nature, privacy, and convenience.

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.

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.