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Compare 53 Villas in Windsor with updated reviews, rates, and availability.

Valley of the Moon Getaway
Outdoor dining

Valley of the Moon Getaway

10.0 out of 10, Exceptional, (220)
"Great outdoor space with great views"
Valley of the Moon Getaway
Pool, 3 Acres, Pool Table, Hot Tub
Your wine counrty escape awaits!

Pool, 3 Acres, Pool Table, Hot Tub

9.8 out of 10, Exceptional, (32)
"This is a gorgeous property, These are the highlights: 1. Airy and spacious 2. The pool and hot tub and pool house! 3. The deck and view of the trees 4. Location, situated close to the highway, but far enough away to allow for a buffer "
Pool, 3 Acres, Pool Table, Hot Tub
Iconia: Historic Mansion, Heated Pool & Hot Tub, 9 Bedrooms

Iconia: Historic Mansion, Heated Pool & Hot Tub, 9 Bedrooms

10.0 out of 10, Exceptional, (4)
"One of a kind property in a beautiful location. The layout was super well suited for our group, with lots of spaces to relax and enjoy each other's time. The host is great - very responsive and kind, with all the amenities you need/expect. Would love to stay at this property again. Thank you so much!"
The price is AED 6,424
AED 10,568 total
includes taxes & fees
28 Dec - 29 Dec
Iconia: Historic Mansion, Heated Pool & Hot Tub, 9 Bedrooms
Year-Round Heated Pool | Hot Tub | Fire Pit | Lawn
The spacious grounds feature comfortable seating around the pool and on the oversized deck overlooking vineyards.

Year-Round Heated Pool | Hot Tub | Fire Pit | Lawn

10.0 out of 10, Exceptional, (31)
"We had the best stay in Kenwood—everything about the house was great for our family vacation. We loved having access to the pool and back patio, and the home was comfortable and well-appointed. Would stay here again in a heartbeat!"
The price is AED 3,104
AED 5,919 total
includes taxes & fees
8 Jan - 9 January 2025
Year-Round Heated Pool | Hot Tub | Fire Pit | Lawn
Secluded Vineyard Estate Healdsburg
Secluded yet close to town plaza

Secluded Vineyard Estate Healdsburg

9.8 out of 10, Exceptional, (116)
"Lovely! There were 6 adults - 2 from Mercer Island, Washington, 2 from Park City, Utah, and 2 from Little Rock, Arkansas. We all loved the accommodations, the amenities and the gorgeous views. We highly recommend!!!"
Secluded Vineyard Estate Healdsburg
Estrella by AvantStay | Secluded Spanish-Style Estate on 7 Acres of Vineyards
Welcome to Estrella.

Estrella by AvantStay | Secluded Spanish-Style Estate on 7 Acres of Vineyards

8.6 out of 10, Excellent, (14)
"This was a family reunion with family from the Bay Area and from the UK. We have stayed at this property before, and we were pleased with the upgrades to the kitchen area. Our stay was magical. The privacy in the extensive grounds, the beautiful pool and well-appointed house set the scene for a great visit. Minor problems with the pool and hot water were attended to immediately by the property management team. We are recommending Estrella to friends who are looking for a similar arrangement"
Estrella by AvantStay | Secluded Spanish-Style Estate on 7 Acres of Vineyards
Sky View: All-Season Heated Pool & Hot Tub, 5 Acres, EV Plug

Sky View: All-Season Heated Pool & Hot Tub, 5 Acres, EV Plug

10.0 out of 10, Exceptional, (24)
"The property was beautiful, with plenty of room to spread out. it was also much cleaner than other VRBOs I've stayed in. "
The price is AED 1,759
AED 3,693 total
includes taxes & fees
13 Jan - 14 January 2025
Sky View: All-Season Heated Pool & Hot Tub, 5 Acres, EV Plug
Heart of Sonoma County, Fountain Grove 4BR/4BA home, pool, spa, outdoor kitchen
Pool

Heart of Sonoma County, Fountain Grove 4BR/4BA home, pool, spa, outdoor kitchen

10.0 out of 10, Exceptional, (1)
"This was a perfect space to come back to after a full day of wine tasting and exploring the Valley. Very spacious, clean, and accommodating of all our needs. The host was prompt with any questions we had and the entire process was as seamless as could be. We will certainly be coming back! Just an amazing property."
Heart of Sonoma County, Fountain Grove 4BR/4BA home, pool, spa, outdoor kitchen
Mountain Serenity: Luxe Pool, Views, Comfort

Mountain Serenity: Luxe Pool, Views, Comfort

10.0 out of 10, Exceptional, (4)
"We had such a great family visit . Thank for your beautiful home! It was so comfortable and clean and had everything we needed for family meals. Would recommend this house to everyone! Our Hosts were so kind and check in and check out were simple. Thank you again!"
The price is AED 2,648
AED 4,712 total
includes taxes & fees
19 Jan - 20 January 2025
Mountain Serenity: Luxe Pool, Views, Comfort
Luxury Napa Estate With Pool/Hot-tub/Concierge

Luxury Napa Estate With Pool/Hot-tub/Concierge

10.0 out of 10, Exceptional, (39)
"This is the second time that we have stayed at Chanric and we have really enjoyed it both times. It is beautiful, updated, clean, well equipped, and well managed. The property manager was accessible, friendly, and helpful. We have been to Napa with various groups many times, but this is where we will stay on future trips!"
The price is AED 3,672
AED 6,556 total
includes taxes & fees
21 Jan - 22 January 2025
Luxury Napa Estate With Pool/Hot-tub/Concierge
Calistoga Wine Ranch Estate

Calistoga Wine Ranch Estate

10.0 out of 10, Exceptional, (82)
"The property was fantastic for our group of 12. The pictures don’t do the house justice. We would all recommend this house to anyone. "
Calistoga Wine Ranch Estate
You Will Dream of this House AND its Views!

You Will Dream of this House AND its Views!

9.4 out of 10, Exceptional, (8)
"Everything about this house was truly spectacular. The views were breathtaking, the house was very modern but inviting with every detail thought of. Comfortable family room perfect for our family of 5 adults to watch movies and play games. The kitchen was fully stocked which made it easy to grill/cook meals. We enjoyed the house and pool so much we decided to eat more meals at home than out. We definitely enjoyed every moment of our stay and hope to return some day!! "
You Will Dream of this House AND its Views!
Titan: Theater, Heated Pool, Gym, Billiards
Large outdoor area directly accessible from the family room (pool table room) and gym.

Titan: Theater, Heated Pool, Gym, Billiards

9.6 out of 10, Exceptional, (8)
"Had a peaceful and chill birthday weekend at the house. We never left it. It was the perfect setting with lots to do - cooking, hanging out, watching a movie, and swimming. We were a group of ten friends with a dog and a baby. Hosts were super fast in communicating. No issues. "
Titan: Theater, Heated Pool, Gym, Billiards
Locanda Winery estate with Olympic-size pool & Starlink WiFi - dog-friendly

Locanda Winery estate with Olympic-size pool & Starlink WiFi - dog-friendly

9.6 out of 10, Exceptional, (26)
"This Property is absolutely Gorgeous! We loved the home and location. I would check in with the management company if I were the owner. Master shower clogged and won’t drain which has caused wall damage. Our two guest rooms had dirty towels and ours were wet. Home is fabulous!!"
Locanda Winery estate with Olympic-size pool & Starlink WiFi - dog-friendly
Stunning Country Retreat, Pool, Hottub, Views, 92 Acres
Pool House living space, a wonderful gathering area

Stunning Country Retreat, Pool, Hottub, Views, 92 Acres

9.6 out of 10, Exceptional, (14)
"Nice space for a big group. We spent most of our time in the farm house because that is where the majority of the group slept. Pool house is very nice and spacious."
Stunning Country Retreat, Pool, Hottub, Views, 92 Acres
Wellington by AvantStay | Secluded Wine Country Estate w/ Gorgeous Mtn Views
Welcome to Wellington.

Wellington by AvantStay | Secluded Wine Country Estate w/ Gorgeous Mtn Views

9.6 out of 10, Exceptional, (18)
"Loved our stay at the house! It was perfect for our group. It was just missing potholders, enough forks for 10 people and a coffee grinder. Even with those things missing it was perfect."
Wellington by AvantStay | Secluded Wine Country Estate w/ Gorgeous Mtn Views
Private 1+ acre, Bocce, New Heated Pool & Hot Tub, Waterfall
This oasis has over an acre of flat land for playing! Bocce court, pool table, outdoor dining, bar and grill pavilion, and a gas-heated pool and spa.

Private 1+ acre, Bocce, New Heated Pool & Hot Tub, Waterfall

10.0 out of 10, Exceptional, (12)
"Nice roomy house close to San Francisco. Easy weekend getaway . Swimming pool was a comfortable temperature and the hot tub heated up fast . The hosts were very responsive and accommodating. "
The price is AED 1,675
AED 3,738 total
includes taxes & fees
6 Jan - 7 January 2025
Private 1+ acre, Bocce, New Heated Pool & Hot Tub, Waterfall
Luxury Executive or Vacation Rental in Kenwood
Exterior

Luxury Executive or Vacation Rental in Kenwood

10.0 out of 10, Exceptional, (8)
"The property easily accommodated 5 couples and had a great outdoor area. Close enough to Sonoma square to drive there but far enough away to have a quiet retreat. Would definitely stay again. "
Luxury Executive or Vacation Rental in Kenwood
Villa Tranquila ~ Historic Mediterranean Home, Mountain Views, Spa!
Tranquility awaits

Villa Tranquila ~ Historic Mediterranean Home, Mountain Views, Spa!

9.6 out of 10, Exceptional, (19)
"We enjoyed the large, roomy premises for our meals in the dining room and family get togethers in the living room. The variety in size of the bedrooms and beds was perfect for our needs."
Villa Tranquila ~ Historic Mediterranean Home, Mountain Views, Spa!
Gorgeous Napa estate 15 mins to St Helena surrounded by vineyards. Permit 138485
Property exterior

Gorgeous Napa estate 15 mins to St Helena surrounded by vineyards. Permit 138485

10.0 out of 10, Exceptional, (9)
"The house was perfect for a group of friends to enjoy the winieries and the beautiful sunset in the evening. "
Gorgeous Napa estate 15 mins to St Helena surrounded by vineyards. Permit 138485
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Windsor

Cottage home near the Russian River; county parks; numerous wineries
Dining

Cottage home near the Russian River; county parks; numerous wineries

10.0 out of 10, Exceptional, (92)
"Property was perfect for me while I was taking care of my grandchildren"
Cottage home near the Russian River; county parks; numerous wineries
Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA

Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA

9.8 out of 10, Exceptional, (7)
"We had a group of 12 ranging in age from 12 to 93 and we all had a wonderful time. The kitchen was well stocked and accommodated multiple cooks for an extensive dinner. The indoor and outdoor games were enjoyed by all ages. The common area was large enough for everyone to enjoy time together, without being cramped or constraining. The front veranda was such a pleasant place to hang out with our morning coffee. The back yard and rear deck had so much available to do that we never got a...
Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH
This silhouette view of the home reveals the inspiring window views at dusk.

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

9.2 out of 10, Wonderful, (185)
"Felicity's home was the perfect place for our retreat. The common spaces were spacious allowing eight of us to easily come together in the comfortable abundant seating in the main living space and around the dining table. The four bedrooms all contained comfortable warm bedding and mattresses with an extra private room for one of us. The hot tub was clean and heated perfectly -- a big plus we look for in our annual retreats. IN addition, it was a true pleasure communicating with Felicity...
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do villas in Windsor cost?
Rates for villas in Windsor range between AED 1,675 and AED 6,424 per night. Whatever your budget, you’re sure to find something that matches your needs with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Windsor?
Windsor has 53 villas to choose from. Find your perfect stay quickly and easily by checking the “Villa” box under the “Property type” tab in our handy filter tool.
Why book your villa in Windsor with Expedia?
Reserving a villa in Windsor is as simple as working out your travel dates and selecting a place that suits your style. Looking for something luxurious or affordable, or a property that also features free WiFi? Use Expedia’s search filters to narrow your results and find the ideal fit.
How can I find cheap villas in Windsor?
Expedia is here to help you track down cheap villas in Windsor. Simply use our filter tool to choose amenities, budget and star rating to refine your search and find an awesome place to stay in a couple of quick clicks.