Guesthouse vacation rentals in Chesterfield County

Guesthouse in Chesterfield

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.

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4.98 out of 5 average rating, 105 reviews

5.0 out of 5 average rating, 18 reviews

The Guest Garage | Private Forest Hill Retreat

Welcome to The Guest Garage—a thoughtfully designed private retreat tucked into Richmond’s beloved Forest Hill neighborhood. Walk to Forest Hill Park, bike the James River trails, explore local cafés, breweries, and restaurants, then return to your own private courtyard to unwind beneath the string lights. With thoughtful design, modern comfort, and an unbeatable location, The Guest Garage is the perfect home base for weekend getaways, business travel, and experiencing Richmond like a local.

LocationWalkabilityAccess

5.0 out of 5 average rating, 112 reviews

The private deck is adorned with hanging ferns, offering a serene outdoor space. A seating area with a small table is visible, surrounded by wooden decking and white railings. Steps lead to a lush garden area, enhancing the sense of privacy.

Guesthouse in The Fan

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!

FamilyLocationHospitality

4.88 out of 5 average rating, 131 reviews

A charming guest house is visible with white siding and vibrant turquoise shutters. The clean, landscaped surroundings include neatly trimmed bushes and a paved walkway leading to the entrance. Tall trees in the background suggest a peaceful, natural setting.

Guesthouse in Midlothian

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

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4.99 out of 5 average rating, 337 reviews

A charming, brick exterior stands prominently along a cobblestone alleyway. The door, framed by a wooden planter, features a simple design. Surrounding buildings are visible in the distance, with natural light filtering through the overcast sky.

Guesthouse in The Fan

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.

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The spacious studio features a queen-sized bed adorned with yellow accents, surrounded by lush greenery. Natural light streams through multiple windows, illuminating modern furnishings, including a kitchenette and a coffee station. A cozy rug lies below, enhancing the inviting atmosphere of the room.

4.96 out of 5 average rating, 344 reviews

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.

LocationValueAccuracy

5.0 out of 5 average rating, 39 reviews

A charming cottage features a light pink exterior and a metal roof, complemented by a covered porch with seating. A fire pit is surrounded by gravel, and various plants are placed around the yard, enhancing the outdoor area's inviting nature.

Guesthouse in Bon Air

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!

LocationFamilyNearby

4.98 out of 5 average rating, 40 reviews

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.

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Guesthouse in Chesterfield

Private Eyrie - Gorgeous View!

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.

LocationValueWalkability

4.95 out of 5 average rating, 330 reviews

A modern kitchen showcases rich wooden cabinetry and sleek stainless steel appliances. The island features two stools and is set with dinnerware, while a washer is discreetly integrated into the design. Natural light filters through a window, enhancing the workspace.

4.98 out of 5 average rating, 61 reviews

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!

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Guesthouse in Chesterfield

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.

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4.92 out of 5 average rating, 36 reviews