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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Guest favourite
A light-colored room features a dark wooden dresser with gold hardware and a framed artwork above it. The view extends toward an adjacent workspace featuring a desk and an ergonomic chair. Soft carpeting covers the floor, enhancing the room's comfort.
Guest suite in Chesterfield
4.81 out of 5 average rating, 63 reviews

the winter clover.

Forget your worries in this spacious non smoking and serene space. This cozy nest is 1.5hr away from the virginia beach, 9min from Pocahontas state park and 30min from downtown Richmond. Guess have access to a coffee machine, toaster, microwave, refrigerator and oven. A queen size bed in the room with queen size air mattress available per request if guess travels with family. Nice walking trail in the community for morning promenade. we require no more than 2 people at all time on the property.

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

Superhost
A spacious dining area features a large table surrounded by six elegantly designed chairs with soft cushions. A decorative plant adds a touch of greenery, while the ceiling displays a modern light fixture. The walls are painted in a soft yellow tone, enhancing the warm atmosphere.
Home in Hopewell
4.81 out of 5 average rating, 180 reviews

Refresh, cheerful home from home.

Relax with the whole family at this peaceful place to stay. A home you surely call home . Newly renovated, professionally decorated to give you the feeling of calmness and enjoyment. Located in the heart of the Tri-cities, near Fort Lee, Southpark Shopping Center, Hopewell marina, the Crossing Shopping Center, convenient store, fast food, gas stations movie theater are minutes away. The house has spacious front, back and left side views with no adjacent neighbors on these three sides.

Guest favourite
Home in Chesterfield County
4.78 out of 5 average rating, 87 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
Guest suite in Huguenot
5 out of 5 average rating, 58 reviews

The Enchanted Studio w/ Tree-Top Views

Some spaces feel different the moment you walk in. The Enchanted Studio is one of them. Perched on the second floor of a beautifully crafted Richmond home, the Enchanted Studio greets you with a wall of windows and a view that stops you — a rain garden, towering trees, and a creek threading quietly along the property's edge. Thoughtfully designed, this retreat works for however you need it: a quiet escape, a remote work base, or simply a place to decompress in a beautiful setting.

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, 118 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, 191 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, 517 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, 49 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.

Guest favourite
A cozy living area features a plush, green sofa adorned with textured cushions. A round wooden coffee table displays decorative bottles and a stack of books. Sunlight filters through a partially draped window, creating a warm ambiance against the rustic log walls.
Cabin in Henrico
4.96 out of 5 average rating, 82 reviews

Parkside Log Cabin

This 1930s log cabin is a peaceful getaway nestled inside the rural National Battlefield Park system while only 20 minutes from all that downtown Richmond has to offer. Overlooking a private pond for canoeing, fishing or stargazing, this property has all the charm of a vintage log cabin but with modern amenities like a fully stocked kitchen, cozy loft for sleeping, and a luxurious bathroom with an oversized shower, complete with plush robes for two.

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.

Popular amenities for Windsor Hills holiday rentals