
Holiday houses in Chesterfield County
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Top-rated holiday rentals in Chesterfield County
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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.

Casa Terra I Pet-Friendly Eco Oasis with Gazebo
Welcome to Casa Terra, your serene urban retreat, perfect for families & furry companions. Tucked away on a sprawling 1/3 acre, this property is a rare gem. Let your dogs run free in the 6-ft fenced backyard or lounge in the screened gazebo. Inside, unwind in the living room with a 55-inch smart TV, or cook in the remodeled chef’s kitchen with an induction stovetop and all the essentials. You'll find two queen bedrooms & a full pullout sofa for additional guests—all designed for a restful stay.

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!

The AlleyLight - Havana Oasis
Welcome to The AlleyLight BnB! A Havana Nights inspired stay. This home is built to teleport you into your own personal world. A romantic setting with warm lighting or a professional getaway with designated work areas. Nestled right into downtown Richmond (the FAN), minutes away from VCU, UR, the business district and Cary Town! Food, Drinks, and fun are just a walk away when you're staying with us. Please note: this is a historic home, the stairs and bathrooms are smaller than modern homes.

Private guest apt on creek w/ patio & fire feature
“The Nest” is a completely private, ground level “basement” apartment. 15 minutes from downtown Richmond & 18 minutes to Pocahontas State Park, this space offers a peaceful, conveniently located, retreat. Private entrance, cozy patio, & large yard- all creek side and professionally designed. Laundry in unit, high speed internet, Smart TV. Yard is wooded and private. Many restaurants and tons of shopping within 5 min of the house, and 2.5 miles from highway access.

Private B&B in Historic Fan
We are looking for people who will enjoy the Historic Fan District of Richmond. The stand alone apartment includes a bedroom, bathroom, and renovated kitchen which has microwave, refrigerator, toaster ,and Keurig coffee machine. For our overnight guests we will provide the ingredients for a delicious breakfast: baked goods butter jams etc., 6 breakfast cereals, , fresh fruit , tea and for Keurig 10 varieties of coffee plus hot chocolate and hot apple cider.

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.

Sixteen West - Modern Apartment in Richmond
Welcome to Sixteen West! This stylish, modern apartment is nestled in the heart of historic Jackson Ward. Recently renovated, the space features beautiful hardwood flooring, updated lighting fixtures, and a sleek, fully equipped kitchen. You'll be within walking distance of some of Richmond’s best spots, including Tarrant's Café, Quirk Hotel, The National, and more! Please note: This unit requires climbing 2.5 flights of stairs — THERE IS NO ELEVATOR.

The Greenhouse 'n the Heart of Midlothian, VA
The Greenhouse is a whimsical refuge located in the very heart of Old Midlothian Village with its old churches and historic houses and is within a 15-20 minute walking distance from several restaurants. You will love staying in our nature inspired home with its resort inspired furnishings; green, leafy décor, fully equipped kitchen, large bathrooms, stocked laundry room, and large yard with gas grill, picnic table and fire pit.

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.

The Creekside Cool Bus
Experience the ultimate glamping adventure in our converted school bus! Nestled on 5 acres of land, the campsite features lush woods and a creek. Enjoy the peace and quiet of nature with the comfort of a home away from home. Our skoolie is the perfect basecamp for outdoor adventures-just 30 minutes to Richmond and 5 minutes from the nearest trailhead at Pocahontas State Park with pass included.

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!
Popular amenities for Chesterfield County holiday rentals
Other great holiday rentals in Chesterfield County

1BR Apt - Stonewall Manor at Keystone

Private room in a sparkling-clean, quiet home!

Shared home w/private bed & bath in N. Churchill

• Private Room in Charming Cottage 5 mins from RVA

Travel and Explore, enjoy this home with Heart

*New* Cottage cheerful in walkable Fan Dist

Willow Tree Breeze-Near VCU&VUU

Richmond Museum District; close to everything!
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