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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Guest favorite
A bright living area features a light-colored sofa positioned against a wall. Two large windows bring in natural light, framed by long orange curtains. An intricate area rug adds color to the floor, while wall art and decorative pieces enhance the space.
Apartment in Petersburgh
5 out of 5 average rating, 16 reviews

The Henry Lofts Unit 3 - 'The Sunset Suite'

The Henry Lofts Unit 3 apartment provides everything you could possibly want; elegance, style...conveniently located in downtown Old Towne Petersburg & 3 miles from Fort Gregg-Adams. Bring your furpal because you have a fully fenced pet friendly yard with a private deck to let your dog outside, along with private parking. This historic building was built in the 1800's & completely renovated with new appliances in 2024. Walk to the local restaurants, museums, and coffee shops in your back yard!

Top guest favorite
A single-story house is framed by a manicured yard featuring green shrubs and small trees. The front porch is covered, providing shade with inviting seating areas. A paved driveway leads to the entrance, enhancing accessibility. Clear skies and sunlight contribute to a bright exterior.
Guesthouse in Chesterfield
4.95 out of 5 average rating, 19 reviews

1-Bedroom w/ private entrance, Patio, & Parking

Private Entrance, 1-bedroom guesthouse with a queen bed, queen sofa bed, full bath, and dedicated parking. Relax in the bright living room or unwind on your private patio. Ideal for couples, solo travelers, or small families. Located in a quiet neighborhood close to shops, dining, and attractions—everything you need for a comfortable stay! There is NO kitchen access. This space comes equipped with a microwave, fridge, coffee pot, and AC/heating unit. Owner lives in the main side of the home.

Top guest favorite
A cozy living area is presented with a light-colored sofa adorned with yellow cushions. Nearby, a dining table with wooden chairs is set against the wall. A functional kitchen area features teal cabinetry and stainless steel appliances, illuminated by soft overhead lighting.
Apartment in Chester
4.96 out of 5 average rating, 23 reviews

Green Door Escape

Forget your worries in this spacious and serene space. Enjoy a comfortable stay with a private entrance, separate from the main house, with parking at your front door. Privacy prevails! A comfortable home away from home. Access to a lush garden. Queen bed, private en-suite bathroom with shower. Fitted kitchen: Induction-stove ( two plate), Air-fry Microwave, Coffee maker, and Refrigerator. Crockery, cutlery, cookware and utensils, provided. Basic cleaning supplies. Linen changed weekly.

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
4.75 out of 5 average rating, 77 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

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, 99 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
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
4.89 out of 5 average rating, 499 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
The living area features natural wood paneling with high ceilings. A comfortable sofa is arranged facing a wall-mounted TV, alongside a wooden coffee table. A staircase leads to the loft, visible above, while a doorway opens to the kitchen area.
Guesthouse in Petersburgh
4.95 out of 5 average rating, 186 reviews

"Lofty Cottage" Adorable 1-Bedroom Guest House

Enjoy this quaint Cozy Cottage with bedroom loft! This adorable 1-bedroom unique place has a style all its own. Built in the 1960’s behind the main house, it has floor to ceiling pine paneling, pine floors and fireplace. It has been recently remodeled with new tiled bathroom , newly remodeled kitchen and stainless steel appliances. A new Heating and Air unit was installed summer 2021. The pine paneling and 16 foot high ceilings gives it that "cottagey" feel.

Guest favorite
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
4.98 out of 5 average rating, 64 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 favorite
A living room area features a brown leather couch positioned against a light-colored wall. A small table holds a bowl of fruit, complemented by a decorative rug underneath. A tall lamp and a display shelf with books and plants provide soft illumination, while a decorative fireplace adds character.
Apartment in Petersburgh
5 out of 5 average rating, 28 reviews

Historic Poplar Lawn

Charming, private apartment in the historic Poplar Lawn neighborhood of Petersburg, right across from beautiful neighborhood park! Cozy and quaint with plenty of space and modern comforts like WiFi, smart TV and well equipped kitchen. Luxury towels and linens are provided. In a nice neighborhood with on and off street parking. Close to Virginia State University, restaurants & antiques in famous Old Towne, Civil War Battlefield parks and more!

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
4.93 out of 5 average rating, 171 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 favorite
The entrance of a historic brick home is graced by a white wooden staircase leading to a dark door. A decorative awning featuring red, white, and blue patterns drapes above the door, with planters positioned on either side. Flanking windows allow natural light to enter.
Home in Petersburgh
4.96 out of 5 average rating, 104 reviews

Historic Home Near Old Town

Private 1850's Greek Revival Home in Historic Petersburg! -Minutes away from Old Town restaurants and shopping -One block from Poplar Lawn Park -Fast wifi, dual zone central ac/heat -Newly renovated first and second floor -Sleeps up to three (couple + one or two singles) *Please read full listing before booking as not everyone will feel comfortable in our lower income neighborhood.

Guest favorite
A spacious living room is highlighted by a large sectional sofa and a glass-top coffee table. Two artworks are displayed on the walls, complemented by sheer curtains allowing natural light to enter. A decorative arrangement of flowers adds a touch of elegance to the space.
Home in Chester
4.95 out of 5 average rating, 59 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