Holiday houses in Windsor Hills

Open 2 acre, Huge yard/drive, K, K, Q bed, 2 bath

Private and spacious 3 bedroom, 2 full bath home on 2 acres. Less than 10 mins to Airport, Winery, Food and Shops Fully equipped kitchen for your cooking needs. Huge driveway and yard to turn around large vehicles, or boat trailers. Plenty of space to unwind and relax while enjoying Deer and other animals passing by. 10 minutes from Richmond Airport (RIC), VA Capital Bike Trail, River Dog Winery, local recreation park and shopping. 15 minutes to Downtown Richmond. 45 minutes to Williamsburg.

Family · Location · Comfort

The Henry Lofts Unit 1 - 'Chloros Lux Collection'

The Henry Lofts studio provides style, convenience, exposed brick & an open floor plan with 800 sq. ft. You will find a fully fenced pet friendly yard to go along with your private parking, & accommodated apartment with all new everything. This historic building was built in the 1800's but completely renovated with all new appliances and systems in 2024! Walk to all of the local breweries, restaurants, museums, galleries, and boutiques in downtown Old Towne Petersburg, VA. Private Deck/Patio

Family · Value · Access

Recline at Timberline, Family friendly!

-Book with confidence, we are Professional hosts -Conveniences of home (Wi-Fi, heated/cooled, appliances,) -Sleeps 6 -Free parking private driveway -Washer and Dryer -Privacy fence in back yard -Screened in back porch -Convenient to grocery store, shopping and entertainment -Pets (dogs), $75 -1 mile from Interstate 95 -Located in low traffic cul-de-sac -Monday trash pickup -Historic location, near Petersburg battlefield, Hopewell, Colonial Heights -Close to Industrial plants -Near Fort Lee

Location · Family · Decor

Nala's Place

Bring the whole family or a group of friends to this great place with lots of room for fun, located between Richmond, VA and Washington, DC: Spacious retreat in prime location. This roomy home offers comfort and convenience, featuring: • Fully equipped kitchen • Multiple bedrooms to accommodate large groups • Less than hour from attractions Busch Gardens, Richmond Convention Center, DC Area Perfect for families, friends, or business travelers seeking a comfortable base to explore the city.

Location · Value · Cleanliness

The Spruce House

The Spruce House is a cozy 1960's rancher, ideal for tourists who loves to explore historic places, traveling health workers, business and workers on special projects, sports tour for local tournaments. The simplicity of this house will welcome you during your stay. Nestled at the heart of the city, but when you look out in the windows, you will enjoy the tranquility of the countryside, the twitting of the birds in the rain forest and the backyard designed to look like a campsite.

Location · Family · Sleep quality

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!

Location · Family · Indoor spaces

Keystone Acres Farm *Enclosed Heated Pool*

Keystone Acres is located in Chesterfield, VA at a beautiful 1000 acre horse farm. On property we have roughly 60 horses owned by different tenants. The brick farm house in which you will be staying in overlooks one of our ponds & multiple horse barns. We have many "internal" roads here and hope you enjoy the farm views. Our 5 bedroom house is perfect for families or friends who want to have a getaway to "unplug" and experience the country life and each other's time.

Family · Location · Barbecue

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.

Location · Family · Check-in

HideawayOasis/VSU/95/FortGreggAdams/FirePT/PoolTBL

Welcome to Our Hidden Oasis! 🌿✨ This cozy retreat is designed with love and thoughtfulness, perfect for small families and intimate connections. Enjoy year-round outdoor fun—roast s’mores by the fire pit, relax on the patio, or challenge friends to a game of pool. Sleep soundly in our comfy beds and wake up refreshed for new adventures. Whether unwinding or making memories, this home is your perfect getaway. We can't wait to host you!

Family · Location · Air conditioning

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.

Location · Family · Cleanliness

Pet-Friendly in Petersburg, VA

Welcome to our warm, pet-friendly home in Petersburg, VA. It’s comfortable, fresh, and practical—perfect for travelers with pets. We love animals, so your furry friends are truly welcome. Located near the historic River Street Market and Petersburg National Battlefield, it’s a great spot to explore and relax. Enjoy a peaceful, cozy retreat where everyone, including your pets, feels at home.

Value · Family · Condition

Luxe Cottage - South Chesterfield

Indulge in a stylish retreat at this recently renovated, charming cottage nestled on a wooded property in South Chesterfield, conveniently close to Ettrick Park and the Ettrick Train Station and just a short drive from South Park Mall, VSU, Fort Lee, and Old Towne Petersburg. Situated a mere 20 minutes south of Richmond, it offers a delightful blend of comfort and convenience for your stay.

Location · Value · Wi-Fi