Vacation rentals in Windsor Hills

Find and book unique accommodations on Airbnb

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

Guesthouse in Church Road

5.0 out of 5 average rating, 133 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

R2,561 ZAR 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!

Feb 23 – Mar 2

R2,605 ZAR per night

Guest favorite

Cabin in Blackstone

4.98 out of 5 average rating, 138 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 16 – 23

R2,172 ZAR 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!

Jul 10 – 17

R2,522 ZAR per night

Guest favorite

Home in Colonial Heights

4.94 out of 5 average rating, 110 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

Jul 11 – 18

R2,031 ZAR 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.

Feb 24 – Mar 3

R2,273 ZAR per night

Guest favorite

Home in Petersburg

4.93 out of 5 average rating, 71 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.

Nov 12 – 19

R2,458 ZAR per night

Guest favorite

Guesthouse in Chesterfield

4.96 out of 5 average rating, 184 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 2 – 9

R2,029 ZAR per night

Guest favorite

Guesthouse in Petersburg

4.94 out of 5 average rating, 142 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.

Sep 9 – 16

R2,252 ZAR per night

Guest favorite

Home in Petersburg

4.94 out of 5 average rating, 35 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.

May 29 – Jun 5

R1,852 ZAR per night

Guest favorite

Guesthouse in Richmond

4.97 out of 5 average rating, 375 reviews

A Place of Peace

A separate cozy cottage for two. Queen sized bed with en-suite full bathroom, plus a screened-in porch and an outside deck. JD, our short-haired orange cat and Ambassador, will be happy to keep you company and share HIS porch!. We are a short drive downtown and a 5-minute walk to the James River. Richmond is a foodie town with great brew-pubs everywhere. All are welcome!

Mar 21 – 28

R1,681 ZAR per night

Guest favorite

Apartment in Colonial Heights

4.93 out of 5 average rating, 15 reviews

Beautiful cozy one bedroom apartment

This is a quiet and cozy apartment right in the center of the tri-cities area. With quick access to I-95 and I-85. Several near by restaurants. This one bedroom apartment is very nice. This apartment is equipped with hardwood floors, stainless steel appliances and black oak cabinets. This apartment is a "one of a kind" place. It is a must see to appreciate!

May 16 – 23

R2,041 ZAR per night