Vacation rentals in Windsor Hills

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Top-rated vacation rentals in Windsor Hills

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Guest favorite

Guesthouse in Church Road

5.0 out of 5 average rating, 132 reviews

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.

Aug 21 – 28

G$27,825 GYD per night

Guest favorite

Cabin in Blackstone

4.98 out of 5 average rating, 133 reviews

Rustic Secluded Cabin at Whetstone Creek Farm

Unwind in your own forest retreat. Enjoy waking up in the king size bed to views of trees, a well appointed open floor plan, and a front porch made for sitting! Listen to rain on the tin roof or enjoy a bonfire in the fire pit after taking a stroll down 2 miles of wooded trails or wading in the creek. Stay connected with high speed wifi. Wildlife abounds on our woodland plant farm. Approximately 15 minutes from Ft. Barfoot, this is the perfect place to stay in Blackstone if you want to get away!

Feb 22 – Mar 1

G$23,871 GYD per night

Guest favorite

Home in Richmond

4.93 out of 5 average rating, 121 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!

Nov 10 – 17

G$27,904 GYD per night

Guest favorite

Apartment in Chester

4.97 out of 5 average rating, 33 reviews

Relaxing Farmhouse: Basement Apartment

Whether passing through, celebrating a graduation at Ft. Gregg-Adams, or simply getting away, bring yourself or the whole family to this taste of country in the midst of the suburbs. Nestled in the heart of Chester, we offer the convenience of proximity with the feel of open spaces. Our open floor plan basement provides space and privacy, and our fenced in backyard boasts a full blown play-at-your-own-risk playground, trampoline, basketball court, garden, fire-pit, and more! Welcome home!

Apr 28 – May 5

G$27,399 GYD per night

Guest favorite

Home in Colonial Heights

4.94 out of 5 average rating, 109 reviews

Quiet Haven Near I-95 & Ft Gregg-Adams/ Petersburg

This is a fantastic place to rest and relax, rewind & rejuvenate. Registered guests only Great space for long term guests, TDY & medical professionals, small families & transit guests Comfy vibes, spacious & comfortable living room, 3 bedrooms w/ sitting areas, ceiling fans & large closets, & bathtub/shower. Desk/work station Turn Key ready: Eat-in, fully equipped kitchen, stainless steel appliances, washer & dryer Linen, cleaning supplies, water, breakfast bars, coffee & tea provided

Jun 30 – Jul 7

G$25,905 GYD per night

Superhost

Boat in Richmond

4.88 out of 5 average rating, 440 reviews

Warm, Cozy and Comfortable Houseboat, Gated Marina

Note: Dates taken? I have two other boats online-- The Cookie B and also--Beautiful Yacht, 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.

Oct 30 – Nov 6

G$24,699 GYD per night

Guest favorite

Home in Colonial Heights

4.99 out of 5 average rating, 76 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.

Jun 29 – Jul 6

G$40,621 GYD per night

Guest favorite

Apartment in Petersburg

4.8 out of 5 average rating, 5 reviews

Cozy + Quaint Loft in Old Towne

Located in a renovated Pepsi bottling plant and Nash car dealership, the Nash offers history with modern furnishings to create the perfect marriage of old and new. Our 1 bedroom, 1 bathroom suite includes a full kitchen, cozy bedroom, spacious living room, dining space and even includes 2 in 1 in-unit laundry! Enjoy all the comforts of home while you're staying with us. The Nash is available for short and long-term stays. 3+ month stays require additional review by our team.

Apr 28 – May 5

G$20,205 GYD per night

Guest favorite

Home in Petersburg

4.93 out of 5 average rating, 70 reviews

The historic John Baird House

Welcome to our charming historic property, nestled in the heart of Old Towne, Petersburg. This remarkable Airbnb offers a unique opportunity to step back in time and experience the grandeur of a bygone era. Dating back to 1783, this historic gem has been lovingly restored while embracing contemporary amenities. This Airbnb boasts two spacious bedrooms, each exuding its own unique charm and character -- all within a short walk to the restaurants and shops of Old Towne.

Feb 22 – Mar 1

G$26,711 GYD per night

Guest favorite

Guesthouse in Chesterfield

4.96 out of 5 average rating, 183 reviews

Gorgeous Creek View from your Private Eyrie

Enjoy a relaxing view of Falling Creek from the second floor apartment with a private entrance and balcony. The wall of windows overlooks a secluded backyard with visiting deer, heron, owls, and other wildlife. Sit by the pond and creek in or fire pit. The property offers off street parking in a safe neighborhood which is located 20 minutes from downtown Richmond, 10 mins to Midlothian and Chesterfield, 3 mins to Swim RVA. 15 mins to the airport or train station.

Aug 11 – 18

G$19,154 GYD per night

Guest favorite

Guesthouse in Petersburg

4.94 out of 5 average rating, 141 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.

Aug 30 – Sep 6

G$24,469 GYD per night

Guest favorite

Treehouse in Richmond

4.88 out of 5 average rating, 119 reviews

Romantic Treehouse for 2 (No Kids) in Little Farm

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. Only adults allowed. Cabin is 10 X 12" of cuteness with all the amenities you might need to feel comfortable, electricity, Smart TV, wifi, coffee maker, memory foam bed, and an awesome outdoor bathroom to shower under the stars!

Dec 31 – Jan 7

G$23,372 GYD per night