Vacation rentals in Windsor Hills

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Top-rated vacation rentals in Windsor Hills

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

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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, 176 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.

Guest favorite
Apartment in Petersburg
4.97 out of 5 average rating, 132 reviews

Bird's-Eye View in the Heart of Historic Old Towne

Enjoy a bird’s-eye view of historic Old Towne Petersburg in this stunning private apartment nestled in the Nathaniel Friend House (built in 1816 & on the U. S. National Register of Historic Places). Simply step downstairs & enjoy a meal at one of the area’s favorite restaurants, Wabi Sabi! Within walking distance to many restaurants, coffee & antique shops, museums, art galleries, breweries & historic sites. National Battlefield, Fort Lee & VSU minutes away. 25 miles from Downtown Richmond.

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

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
The open living area features warm wood flooring, exposed brick walls, and a cozy seating arrangement. A traditional area rug lies across the floor, with a fireplace visible in the background. A dining area with wooden chairs and a kitchen can be seen, enhancing the inviting space.
Home in Petersburg
4.93 out of 5 average rating, 103 reviews

1830's House in Historic Old Towne Petersburg, VA

This circa 1830 storefront home was recently renovated. The second floor living quarters, fully furnished with a gourmet kitchen, super living room, study, large master bedroom and bath complete with antique claw-foot bathtub, sliding warehouse doors and much more can be yours for a surprisingly low price. Complete with original pine flooring and furnished with a combination of old and new touches. Walking distance to historic Old Towne Petersburg and ten minutes to Fort Lee.

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, 525 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.

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 Petersburg
4.94 out of 5 average rating, 233 reviews

Petersburg Home away from Home

Brick rancher with Tv/xfinity flex, wifi, ring camera system/new kitchen/bathroom, totally remodeled stainless steel refrigerator, stove, microwave, and dishwasher. Central heat and AC with ceiling fans in every room. Laundry room for your convenience that leads out to a screened porch and fenced in backyard. Six miles from Fort Gregg-Adams Military Base. Four miles from Virginia State University. Seven miles from Virginia Motorsports Park.

Top guest favorite
Home in Richmond
5.0 out of 5 average rating, 19 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, 200 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 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.

Popular amenities for Windsor Hills vacation rentals