Holiday houses in Chesterfield County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chesterfield County

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

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Superhost
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
4.78 out of 5 average rating, 79 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.

LocationValueParks

Top Guest favourite
Guesthouse in Chesterfield
4.98 out of 5 average rating, 100 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.

FamilyValueQuiet

Top Guest favourite
The private bedroom is accessed through a stylish door featuring the number 203. Inside, a queen-size bed is positioned against a large window with floor-to-ceiling curtains. A contemporary wardrobe is placed nearby, and a textured rug complements the wooden flooring.
Apartment in Church Hill
4.98 out of 5 average rating, 362 reviews

Stunning Modern Studio Will Take Your Breath Away

In Church Hill, cultures intersect to create one of Richmond, VA's most diverse, hip, and walkable neighborhoods. With picture perfect views of the skyline from Jefferson Park, cuisine from award-winning eateries and local shopping boutiques, Church Hill has something for everyone, is close to everything (10 min from airport, right next to downtown), and delivers a uniquely rich way to experience the Virginia's capital. We’re booking now for staycations, vacations, and all things in between.

LocationFamilySolo travel

Top Guest favourite
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, 633 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

LocationFamilyLaundry

Top Guest favourite
The Tudor-style home is set on a spacious lawn, framed by mature trees. The property features large windows, showcasing the inviting interior, complemented by well-maintained landscaping and brick accents. A sense of tranquility is evoked by the home's elegant design and lush surroundings.
Home in Richmond
5.0 out of 5 average rating, 35 reviews

AllSeaZens Oasis

Our Tutor home features five bedrooms, including a media room. The master bedroom on the ground floor boasts a king-sized bed and a fireplace, while the other bedrooms include three queen-sized beds and two inflatable mattresses. The home has 3 Full Baths and a powder room. Enjoy various leisure areas like a media room, speakeasy, great room, fish tank room, and sunroom, all designed for relaxation. ALLSeaZen’s Oasis invites you to experience true tranquility and mindfulness.

LocationFamilyKitchen

Guest favourite
Home in Chesterfield
4.88 out of 5 average rating, 41 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!

ValueFamilyGetting around

Top Guest favourite
Guesthouse in Chesterfield
4.95 out of 5 average rating, 324 reviews

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.

FamilyValueLong stay

Top Guest favourite
Home in Richmond
5.0 out of 5 average rating, 14 reviews

Waterfront Escape | Hot Tub, Canoe & SUP

Welcome to Rushes Reservoir—a waterfront retreat with treetop views hidden in the heart of Richmond. Perched above the reservoir, the home's main living spaces feel suspended in the canopy, with sweeping views of the woods and water. Relax in the hot tub, gather around the fire pit, paddle the reservoir by canoe or SUP, fish from the dock, or unwind on the expansive deck—all just minutes from Richmond's restaurants, breweries, and attractions.

LocationFamilyCheck-in

Guest favourite
Guesthouse in Chesterfield
4.9 out of 5 average rating, 30 reviews

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.

ValueLocationAccuracy

Top Guest favourite
Guest suite in Midlothian
4.95 out of 5 average rating, 61 reviews

Cozy Hideaway guest suite

"The Hideaway" is a spacious and cozy, ground level basement guest suite with easy access to everything in Midlothian. This space offers a convenient, private entrance from the driveway, washer/dryer, high speed internet, 65" smart tv with free Peacock, Netflix, Hulu, Disney, ESPN, Max, Discovery Plus, Paramount, Prime Video, to just name a few. Shared access to the fenced in back yard with a grill and firepit.

ValueFamilyAccess

Superhost
A rustic wooden cabin is elevated among tall trees, featuring a large window that allows natural light to enter. The structure is supported by wooden stilts, surrounded by dense foliage and branches, creating a secluded atmosphere.
Treehouse in Richmond
4.89 out of 5 average rating, 257 reviews

Romantic Treehouse for 2 in Farm (no kids)

Surrounded by trees and peace in our small farm in a neighborhood, this cozy little cabin is made for secluded romantic stays and to enjoy a relaxing and restful night. Not suitable for children. Cabin is 10 X 12" of cuteness with all the amenities you might need to feel comfortable, electricity, heater, Smart TV, wifi, coffee maker, memory foam bed, and an awesome outdoor bathroom to shower under the stars!

LocationFamilyBarbecue

Guest favourite
Home in Hopewell
4.91 out of 5 average rating, 35 reviews

The House on the River!

Relax with the whole family at this peaceful place to stay. This amazing property offers immediately access to the Appomattox River for a fun recreational time. features 4 bedrooms and a separate studio apartment with nice Bathrooms and a Gourmets Kitchens. Plenty of natural light and a friendly neighborhood. Make this beautiful home your next family getaway. No large party/celebration allowed.

FamilyLocationAccess

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