Guest house holiday rentals in Chesterfield County

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.

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.

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.

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.

Charming Carriage House in the heart of the Fan.

Our 112-year-old carriage house has been thoughtfully updated to include modern amenities while maintaining the charm of the original structure. We are within walking distance of hundreds of local eateries, several parks, the James River park system, The Virginia Museum, and plenty of boutique shopping. There is no better location if you want to relax in comfort, consume your way through renowned restaurants & breweries, and immerse yourself in city living.

The Cottage at Maymont

Modern Maymont Guesthouse – Private Studio with Fire Pit Stay in this stylish guesthouse studio in Richmond’s Maymont neighborhood. With vaulted ceilings, a full kitchen, and a cozy queen bed, and pull-out sofa. It’s perfect for solo travelers, couples, or work trips. Enjoy the private patio with a fire pit for relaxing evenings. Walk to Maymont Park, Carytown, and local spots. A well-designed, comfortable stay in a great location—book now!

Funky & colorful private guesthouse with parking!

This unique place has a style all its own with carefully curated touches of yellow! A private guesthouse tucked away and at the top of a spiral staircase. This space is a five minute drive from Richmond's most popular neighborhoods. Fully equipped with a mid-century modern kitchenette, private patio, and A/C! This space is an experience in itself. Explore Richmond's best kept secret; the Yellow Tiger's Den.

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!

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.