Vacation rentals in Windsor Hills

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windsor Hills

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

1 of 1 pages1 / 1
Top guest favorite
A modern kitchen features light-colored cabinetry and a spacious island with a marbled countertop. Stainless steel appliances are integrated, including a microwave and a coffee maker. Natural light is provided by a window above the sink, enhancing the functional layout of the space.
Home in Richmond
4.98 out of 5 average rating, 177 reviews

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.

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
5.0 out of 5 average rating, 50 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

Superhost
A dining area features a wooden table set for four, complemented by a vase of white tulips. The kitchen is visible in the background, showcasing white cabinetry and modern appliances. Natural light fills the space, enhancing the welcoming atmosphere.
Home in Chesterfield County
4.78 out of 5 average rating, 93 reviews

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

Guest favorite
The living room features a large television displaying a coastal scene. Two blue armchairs are positioned near a coffee table, which holds a vase of flowers. Natural light filters through the window with white blinds, illuminating the space with a cozy ambiance.
Home in Petersburg
4.94 out of 5 average rating, 62 reviews

Cozy Sweet Home!

ONLY 10 MINUTES to Ft.Lee!! Enjoy having the whole house to yourself! Make a meal in the kitchen, watch TV while stretched out on the couch, and snuggle up in one of the queen size beds. We have 3 bedrooms each with a Queen Bed, and a Queen Pull out Coach Bed. Every Bedroom also has a TV!! We also have an additional Two(2) Air Mattress. Total we can sleep 10-12. We have USB charging cables in every room. Our goal is to create a comfortable stay that is relaxing and convenient for all.

Top guest favorite
A bedside table is shown beside a spacious bed, topped with a vase of colorful flowers and a magazine. Soft white bedding and multiple pillows are arranged on the bed, complemented by a lamp casting a warm glow against a softly colored wall.
Home in Colonial Heights
4.97 out of 5 average rating, 111 reviews

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.

Guest favorite
An enclosed pool area features a turquoise swimming pool, surrounded by large glass panels that provide views of the outdoor landscape. Two blue lounge chairs are positioned near the pool, creating a calming space for relaxation.
Farm stay in Chesterfield
4.95 out of 5 average rating, 132 reviews

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.

Top guest favorite
Home in Richmond
5.0 out of 5 average rating, 20 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.

Top guest favorite
A covered outdoor entertaining area features comfortable seating arranged around a fire pit. Soft lighting strung above creates a warm ambiance. The space is complemented by decorative plants and cushioned sofas, providing a cozy environment for gatherings.
Home in Colonial Heights
4.94 out of 5 average rating, 202 reviews

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!

Superhost
Home in Hopewell
4.92 out of 5 average rating, 36 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.

Guest favorite
A well-lit sleeping area features two spacious beds, each dressed with checkered bedding. A nightstand holds a lamp beside the beds, while a window allows natural light to fill the room. Warm wooden floors contribute to the inviting atmosphere.
Home in Petersburg
4.9 out of 5 average rating, 69 reviews

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.

Guest favorite
A cozy living area is enhanced by natural light from two large windows, featuring a comfortable red sofa and a patterned rug. A modern TV is positioned on a stand against a light grey wall, beside a stylish glass coffee table.
Home in Petersburg
4.9 out of 5 average rating, 58 reviews

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.

Superhost
Home in Chester
4.88 out of 5 average rating, 113 reviews

Brand new, beautiful home.

This new built home, with 1570 sf , fresh from driveway to kitchen, welcomes you. Come, Relax with the whole family at this brand new elegant, peaceful place to stay. The house is in a quiet, peaceful Chester neighborhood, minutes from Amazon warehouse, Capital One, Lego Land. Cinema Cafe, Fort Greg-Adam, Richmond downtown, Richmond Airport are less than 30’. You’ll love it.

Popular amenities for Windsor Hills vacation rentals