Holiday rentals in Windsor Hills

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Top-rated holiday rentals in Windsor Hills

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

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Superhost
A cozy treehouse cabin is illuminated by warm light, set among tall trees in a wooded area. A wooden bridge leads to the entrance, with a fire pit nearby surrounded by chairs. Soft string lights hang, adding a gentle glow to the space.
Treehouse in Sandston
4.99 out of 5 average rating, 286 reviews

Treehouse in the woods w/AC & heat (bath at house)

Cozy "treehouse" cabin with AC and heat tucked in the woods, with bridge for easy entry. Large windows overlook stream. Site has picnic table and fire ring. Full-size Purple mattress in loft. 80 Mb WiFi, 4KTV. Outdoor hot tub on the deck of our home and outdoor sauna are open 24/7. Trails are closed at treehouse, but many trails available nearby. Fridge, microwave, Keurig. No bathroom at treehouse, but guests have exclusive use of our guest bathroom in our main house anytime - just a short walk.

Guest favourite
A spacious living area features exposed brick walls, creating a rustic charm. A plush gray sofa and two green chairs are arranged around a small table. A modern electric fireplace provides warmth, while a wall-mounted television adds contemporary convenience. Large windows allow natural light to fill the room.
Flat in Petersburgh
4.98 out of 5 average rating, 49 reviews

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

Guest favourite
Home in Chesterfield County
4.78 out of 5 average rating, 86 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 L

Top guest favourite
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, 105 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.

Top guest favourite
A wooden deck offers a comfortable outdoor space, featuring two rocking chairs with floral cushions. A small table stands neatly between them, adorned with a vase of flowers. Surrounding trees showcase autumn foliage, creating a serene backdrop.
Cabin in Dinwiddie
5 out of 5 average rating, 117 reviews

Dinwiddie Couples Getaway- Wells Cabin @WeldanPond

Wells Cabin @Weldan Pond is a beautiful new space designed for couples who love to relax, enjoy the outdoors (hike, fish, trail bike, & more), & marvel over beautiful views. The Cottage has a full kitchen, a large king bedroom, a bright, window filled sitting area, and a new deck overlooking Upper Weldan Pond and acres of healthy, natural hardwood forest with nearly 4 miles of trails to explore. You'll also love just enjoying the deck and the beauty of the Virginia countryside.

Top guest favourite
Tiny home in Richmond
4.99 out of 5 average rating, 189 reviews

The Barkin’ B & B

Just five minutes from the airport and downtown, this cozy tiny home offers rustic charm and modern comfort. Fully equipped with kitchen essentials, books, games, and even coloring books, it’s perfect for relaxing. Pet-friendly, it comes stocked with dog treats, chews, toys, and a large fenced-in backyard for furry companions to enjoy. Conveniently located for travelers, it provides a peaceful retreat while keeping you close to city attractions. A perfect home away from home!

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, 516 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 favourite
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 Petersburgh
4.94 out of 5 average rating, 48 reviews

Cozy Sweet Home!

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 favourite
Home in Petersburgh
4.94 out of 5 average rating, 224 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 favourite
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, 191 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!

Guest favourite
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 Petersburgh
4.9 out of 5 average rating, 49 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.

Guest favourite
A single-story home is shown with light yellow siding and blue shutters. Twin front windows allow natural light to enter, and a welcoming front porch features a blue door. Neatly maintained landscaping surrounds the porch, and a grassy area is visible in the foreground.
Home in Petersburgh
4.88 out of 5 average rating, 147 reviews

Quiet relaxing stay in a trendy 3 bedroom home.

Enjoy a relaxing stay at the wright rd house. Conveniently located off of I-95 in a quiet neighborhood, in a friendly Community. During your stay you’ll experience a comfortable three bedroom home, That has just been completely renovated with a new driveway. To ensure your comfort we’ve provided plush linens and comfortable beds for a good night sleep.

Popular amenities for Windsor Hills holiday rentals