Vacation rentals in Chesterfield Court House

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Top-rated vacation rentals in Chesterfield Court House

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A comfortable living area features a brown leather sectional couch with a matching armchair and ottoman. A round table sits on a patterned rug, while soft natural light filters through the window blinds. Two framed animal prints adorn the light-colored wall.
Home in Richmond
4.91 out of 5 average rating, 249 reviews

Luxury BOHO upper unit

Relax in this calm, stylish 3 bedroom/2 full bath upper level unit. Another Airbnb is in the finished basement unit. The space is completely yours and no access to the other basement unit. Only shared area is the back deck. Unit has a completely updated kitchen with stainless steal and granite. Master bedroom has a super comfy queen bed and a master bath that has a beautiful walk in shower. Guest room has another queen bed and office area has a futon. Elegance and romantic boho style throughout!

Guest favorite
A light-colored room features a dark wooden dresser with gold hardware and a framed artwork above it. The view extends toward an adjacent workspace featuring a desk and an ergonomic chair. Soft carpeting covers the floor, enhancing the room's comfort.
Guest suite in Chesterfield
4.82 out of 5 average rating, 73 reviews

the winter clover.

Forget your worries in this spacious non smoking and serene space. This cozy nest is 1.5hr away from the virginia beach, 9min from Pocahontas state park and 30min from downtown Richmond. Guess have access to a coffee machine, toaster, microwave, refrigerator and oven. A queen size bed in the room with queen size air mattress available per request if guess travels with family. Nice walking trail in the community for morning promenade. we require no more than 2 people at all time on the property.

Top guest favorite
Guesthouse in Chesterfield
4.98 out of 5 average rating, 98 reviews

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.

Superhost
A cozy living area features a light-colored sofa with decorative pillows, positioned next to a stone fireplace. A wooden dining table is visible, along with a lush green plant. Wall art and decorative plates add character to the space, illuminated by natural light from the window.
Apartment in Chesterfield
4.82 out of 5 average rating, 390 reviews

Private guest apt on creek w/ patio & fire feature

“The Nest” is a private, ground level “basement” apartment. 15 min from downtown Richmond & 18 min to Pocahontas State Park, this space offers a peaceful, conveniently located, retreat. Private entrance, cozy patio, & large yard- all creek side. Laundry, high speed internet, Smart TV. Yard is wooded and private. Restaurants and tons of shopping within 5 min of the house, and 2.5 miles from highway access. A friend rents the upstairs of the home, which is completely separate- no shared space.

Guest favorite
The treehouse is illuminated at night, showcasing its inviting wooden structure with large windows. A bridge leads to the main entrance, surrounded by trees. Soft lights adorn the deck and outdoor area, creating a warm and welcoming ambiance.
Treehouse in Richmond
4.97 out of 5 average rating, 630 reviews

Trailside Treehouse - Riverside in Richmond, VA

Fulfill your childhood dream of camping in a treehouse! From this central spot, easily explore the trails and river. Then, relax on the deck and enjoy the magic of the trees. •Airbnb “Top 20 Places to Stay in VA” •"Best of Richmond" by Style Magazine •Featured in Airbnb article on hospitality •One of "8 Great Airbnbs" in the U.S. by Inside Hook •Comes with bathroom, kitchenette & lounge apartment in host house •Dog-friendly Social media: @trailside_treehouse City permit #BLDR-107741-2022

Top guest favorite
A well-equipped kitchen features wooden cabinetry and a modern design. Stainless steel appliances, including a refrigerator and microwave, complement the white countertops. An island with seating offers additional space, while decorative floral backsplash adds a touch of charm. Natural light brightens the room through nearby windows.
Home in Richmond
5 out of 5 average rating, 37 reviews

Stay Awhile - Private, Large Yard, Easy Travel

Welcome to the Exurbs! Peaceful property, not quite rural, not quite the suburbs. Still close enough to jump on the interstate and get where ever you need to be fairly quicky. This property has a huge fully fenced back yard, with plenty of room to unwind and relax on the front/back porch. Bring your boats and trailers, plenty of room! Interstate 288: 3 min Interstate 95 Interchange: 5 min Defense Supply: 6 min Chester: 10 min Dutch Gap Boat: 13 min RIC Airport: 20 min Fort Gregg: 20 min

Top guest favorite
A modern two-story townhome features a blend of siding and stone on the exterior. The driveway is spacious, providing access to a single-car garage on the left. Nearby, a landscaped yard enhances the entryway, with tall trees visible in the background.
Townhouse in Richmond
4.98 out of 5 average rating, 51 reviews

Top Location Cozy Stay - Near Richmond

Discover this brand-new, stylish home designed for comfort and privacy near Richmond. With 5-star guest experiences, this space offers 3 spacious bedrooms, 2.5 modern bathrooms, and a main-level master suite with a remote-controlled reclining bed. Enjoy a bright living area with a large TV, a fully equipped kitchen with island, dining space, private rear porch, garage, driveway, and in-unit laundry. Perfect for families, professionals, or extended stays. Note: Basement has no shared access.

Guest favorite
A cozy living room features a sectional sofa with decorative cushions, including a red heart pillow. Two glass coffee tables sit on a light area rug, while ceiling fan blades and wide windows with sheer curtains provide a bright and comfortable atmosphere.
Home in Chesterfield
4.86 out of 5 average rating, 35 reviews

Charming Retreat w/ Pool Table in Chesterfield!

Escape to this spacious home in Chesterfield, VA! Relax in a cozy living room with Roku TV or cook in the fully equipped kitchen with island seating and a coffee corner. Enjoy the rec room with a pool table, laundry nook, and extra TV. The master suite features a king bed, plush seating, and attached bathroom, while two additional bedrooms offer comfort and storage. A second bathroom, roomy deck with grill, and large backyard complete the perfect retreat. Book your stay today!

Top guest favorite
Tiny home in Richmond
4.99 out of 5 average rating, 203 reviews

The Barkin’ B & B

Just five minutes from the airport and downtown, this cozy tiny home offers rustic charm and modern comfort. Fully equipped with kitchen essentials, books, games, and even coloring books, it’s perfect for relaxing. Pet-friendly, it comes stocked with dog treats, chews, toys, and a large fenced-in backyard for furry companions to enjoy. Conveniently located for travelers, it provides a peaceful retreat while keeping you close to city attractions. A perfect home away from home!

Superhost
A houseboat, painted in blue and white, is docked next to a wooden marina. Surrounding greenery provides a natural backdrop, while a wooden structure with a red roof is visible in the background, showcasing a peaceful riverside setting.
Boat in Richmond
4.88 out of 5 average rating, 520 reviews

Warm, Cozy and Comfortable Houseboat, Gated Marina

Note: Dates taken? I have one other boat online-- The Cookie B with beautiful river views. We offer no contact boarding if desired and we understand the need for a clean place to stay. Therefore we go beyond the recommended guidelines concerning sanitation by fogging the entire boat after each guests departure. And for dining, you can cook aboard or enjoy the Lily Pad Cafe, an outdoor covered and heated restaurant on the river, and it is only two miles from the marina.

Top guest favorite
Guesthouse in Chesterfield
4.95 out of 5 average rating, 318 reviews

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.

Guest favorite
Home in Richmond
4.95 out of 5 average rating, 55 reviews

The Villa on Falling Creek.

🌿 Creekside Villa | Nature Retreat + Monthly Stays Welcome Private 3BR/2.5BA on 1.5 acres inside a 40-acre park. Fall asleep to a creek, wake up to birdsong — yet minutes from VCU, UofR, top restaurants & breweries. Perfect for travel nurses, students, or a local weekend escape. Fast WiFi, full kitchen, cozy fire pit, massage bed & flexible monthly rates. Richmond’s hidden gem — where nature meets city convenience. Book your escape today!

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