Holiday rentals in Windsor Hills

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Top-rated holiday rentals in Windsor Hills

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Top guest favourite
A comfortable living area features a brown leather sectional couch with a matching armchair and ottoman. A round table sits on a patterned rug, while soft natural light filters through the window blinds. Two framed animal prints adorn the light-colored wall.
Home in Richmond
4.91 out of 5 average rating, 240 reviews

Luxury BOHO upper unit

Relax in this calm, stylish 3 bedroom/2 full bath upper level unit. Another Airbnb is in the finished basement unit. The space is completely yours and no access to the other basement unit. Only shared area is the back deck. Unit has a completely updated kitchen with stainless steal and granite. Master bedroom has a super comfy queen bed and a master bath that has a beautiful walk in shower. Guest room has another queen bed and office area has a futon. Elegance and romantic boho style throughout!

Top guest favourite
Cottage in Dinwiddie
4.98 out of 5 average rating, 141 reviews

Country Getaway, Entire Cottage, Modern & Private

Sitting at the forest’s edge with 12’ of glass doors, Daniel Cottage has: - Huge deck w/propane grill & fire pit, cafe table & lots of seating. - Comfy Great Room has HD tv +Netflix/Prime & fully equipped kitchen w/table for 4. - Then add two queen bedrooms - Put it all at the edge of 75 acres of beautiful, natural forest ready to be explored. Two ponds (4 & 6 acres) offer fine fishing. Hike the 3+ miles of pond & forest trails or sit back & enjoy the beauty of the Virginia countryside.

Guest favourite
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
4.77 out of 5 average rating, 84 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, 103 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
Tiny home in Richmond
4.99 out of 5 average rating, 180 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!

Guest favourite
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, 512 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
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, 78 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
A welcoming living area features a comfortable sectional sofa and a large armchair, complemented by a decorative area rug. A smart TV is positioned on a white console, while a green plant adds a touch of nature. Natural light streams in through the front door and windows.
Home in Petersburgh
4.94 out of 5 average rating, 221 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 spacious exterior view of a modern two-story home is presented, featuring a large, brown garage door and an inviting entryway with steps leading to the front door. The surrounding area includes a gravel driveway and a grassy yard, framed by trees in the background.
Guest house in Chesterfield
4.89 out of 5 average rating, 18 reviews

Comfortable 1-Bedroom Apartment

This brand-new 1-bedroom, 1-bathroom in-law suite offers the perfect blend of comfort and style. This home is ideal for those who appreciate both functionality and aesthetics. Enjoy easy access to local hiking and biking trails, perfect for outdoor enthusiasts or those who love to explore nature. Within minutes from shopping centers. With its private entrance and modern amenities, this suite provides both convenience and tranquility.

Top guest favourite
A rustic wooden cabin is elevated among tall trees, featuring a large window that allows natural light to enter. The structure is supported by wooden stilts, surrounded by dense foliage and branches, creating a secluded atmosphere.
Treehouse in Richmond
4.91 out of 5 average rating, 237 reviews

Romantic Treehouse for 2 in Farm (no kids)

Surrounded by trees and peace in our small farm in a neighborhood, this cozy little cabin is made for secluded romantic stays and to enjoy a relaxing and restful night. Not suitable for children. Cabin is 10 X 12" of cuteness with all the amenities you might need to feel comfortable, electricity, heater, Smart TV, wifi, coffee maker, memory foam bed, and an awesome outdoor bathroom to shower under the stars!

Top guest favourite
A modern living area features a comfortable couch with decorative pillows. Natural light filters through windows beside rustic wooden doors. A small coffee table sits on a textured rug, accompanied by a stylish chair, enhancing the inviting and open feel of the space.
Guest suite in Forest Hill
4.98 out of 5 average rating, 805 reviews

Forest Hill Modern Guest House

Located in Richmond's charming and historic Forest Hill neighborhood just blocks from the James River Park and next door to Forest Hill Park. A modern studio space with a king-size bed and a comfy couch in a private guest house. 1 bath with a spacious shower and simple kitchenette. A great overnight space or comfortable stay for those wanting to explore the cities great food, breweries, parks, and trails!

Superhost
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, 116 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.

Popular amenities for Windsor Hills holiday rentals