Guesthouse 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.

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.

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!

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.

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!

Funky & colorful private guesthouse with parking!

This unique guesthouse features curated touches of yellow and sits atop a spiral staircase for a private, tucked-away feel. Located in Richmond’s historic Battery Park neighborhood, you’re minutes from an exciting new food scene, major attractions, and easy highway access. Enjoy a mid-century modern kitchenette, private patio, and A/C. Welcome to the Yellow Tiger’s Den.

Carytown home, King bed, Easy parking

This special place is close to everything, making it easy to plan your visit. *1 level house, almost no stairs in entire house! ( only one step stair to the bathroom area) *Plenty of free street parking, just several steps from the house! *Minutes from everything! In the heart of Carytown! *Pet friendly! This is truly a perfect place for leisure or business travel.