Guesthouse vacation 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.

Cozy Nest Near The River

Cozy and comfortable, fully appointed apartment south of the river. Easy access to the wooded trails and river views of the James River Park system. Charming neighborhood restaurants. A quick and easy drive or bus ride to Richmond's downtown and Virginia Commonwealth University's quirky urban campus. Aveda products, plush linens, and complementary Nespresso coffee and tea. Perfect for someone who wants to enjoy all that Richmond has to offer and end the day in a place that feels like home.

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!

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.

The Carriage House

Enjoy a stylish experience at this centrally-located, cozy guest house. with easy access to James River Park, Downtown, Carytown. Fully renovated space with everything needed for a comfortable short-term stay, fully stocked kitchen with stove, dishwasher, refrigerator & coffee maker. Spacious bathroom and bedroom with king bed. Private entrance with key pad for easy access. Please note, bedroom is located on the 2nd floor, bathroom is located on the ground floor.

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.

Classy Carriage House in Vibrant Museum District

Welcome to an elegant and modern Carriage House nestled at the intersection of Richmond’s most vibrant and historic neighborhoods—The Museum District, The Fan, and Carytown. With its unbeatable location, you’re steps away from museums, trendy shops, delicious restaurants, and lively cafés. Whether you’re in the mood for culture, shopping, or a night out, everything you need is within a few minutes’ walk. Experience the best of Richmond right outside your door!

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.