Holiday houses in Windsor Hills

Heron Rock: Lakefront Cottage on Lake Chesdin

Enjoy peaceful lakefront living at Heron Rock Cottage, where you can stroll through the woods, swim or fish off the dock, paddle the lake in kayaks, or simply relax and enjoy the wildlife and beautiful sunsets. Situated on 6 acres in Dinwiddie County, this newly renovated cottage includes 2 bedrooms, full bath, full kitchen, living room with fireplace and private patio with dining area. Your stay includes full access to the grounds and dock and you are welcome to tie up a boat if you bring one.

Charming, Private Abode: Serenity in Hopewell, VA!

Welcome to our private 1 bedroom, 1 bathroom abode! Our charming home is the perfect place for your stay in the heart of Hopewell, VA. Ideal for a couple’s retreat, a couple of friends or a solo traveler. Conveniently located near popular attractions, dining options & shops. With its cozy & cool atmosphere, you'll feel right at home during your stay. We look forward to hosting you at our home, where comfort & convenience await. Book your stay today & enjoy a memorable experience in Hopewell, VA!

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.

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.

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

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

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.

"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.

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!

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!

2-Bedroom oasis in Chesterfield

Welcome and enjoy your small town living in this newly renovated home that centrally located. . The home has a fully stocked kitchen, patio, backyard, fireplace, Streaming devices on the TV, books, towels and linen provided, along with the basic essentials of privacy and convenience. This space is great option for our military friends, traveling health care professionals or those stopping by on a road trip.

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.