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Featured Condo Rentals in Windsor

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
A heated pool
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
9.2 out of 10, Wonderful, (39)
"Worldmark Windsor is an excellently maintained resort near a neighborhood with a lot of walking options. Close to many wineries, it is a great place to stay. The condo was clean and had a great kitchen. I would definitely stay here again when visiting the wine country."
The price is AU$840
includes taxes & fees
1 Oct - 2 Oct
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Worldmark Windsor/Healdsburg Wine country 3BR 2BATH Sleeps8 Instabook!!
Outdoor pool, a heated pool
Worldmark Windsor/Healdsburg Wine country 3BR 2BATH Sleeps8 Instabook!!
9.2 out of 10, Wonderful, (7)
"Think of this place as a home away from home. It has everything you need to cook meals and fridge, dishwasher, washer and dryer, oven with some baking sheets. I would recommend that if you are going to be doing the majority of cooking there to bring your own oils, spices, aluminum foil and plastic wrap. The unit was immaculate! All the units have a grill and patio furniture. The bathrooms were super clean and spacious! My unit had an extra bed in the living room, Murphy bed."
Worldmark Windsor/Healdsburg Wine country 3BR 2BATH Sleeps8 Instabook!!
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos
A heated pool
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos
3.0 star property
8.4 out of 10, Very good, (8)
"Enjoyed location and proximity to Healdsburg."
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos
Wine Country Beautiful Worldmark 2Bedroom Resort
Outdoor dining
Wine Country Beautiful Worldmark 2Bedroom Resort
9.4 out of 10, Exceptional, (65)
"A comfortable, up-to-date alternative to hotels in the area, with plenty of resort-style and family-friendly amenities."
Wine Country Beautiful Worldmark 2Bedroom Resort
León by Avantstay Private Breathtaking Character Cottage w/ Pool & Hot Tub
Outdoor pool
León by Avantstay Private Breathtaking Character Cottage w/ Pool & Hot Tub
3.5 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home with excellent set up. Spacious, comfortable and in a safe private location. We used the hot tub as it was winter when we came and it was wonderful. Everything was very clean and in working condition. "
León by Avantstay Private Breathtaking Character Cottage w/ Pool & Hot Tub
Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views
Interior
Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views
3.5 star property
Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views
Mataro by Avantstay Large & Elegant Home in Santa Rosa w/ Hot Tub & Games
Interior
Mataro by Avantstay Large & Elegant Home in Santa Rosa w/ Hot Tub & Games
3.5 star property
2.0 out of 10, (1)
"Property canceled our stay two days before our arrival. Awful communication and still trying to get our money back even though Avantstay canceled our accommodations on us!"
Mataro by Avantstay Large & Elegant Home in Santa Rosa w/ Hot Tub & Games
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!
Outdoor pool, a heated pool
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!
9.6 out of 10, Exceptional, (27)
"Very nice and convenient place. Only hiccup was checking in. It was to be available at 4 pm. Did not get our room till 7 pm"
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!
Stylish Condo Steps from St. Helena Wineries & Downtown
Fridge, microwave, oven, stovetop
Stylish Condo Steps from St. Helena Wineries & Downtown
10.0 out of 10, Exceptional, (3)
"I could not have asked for a better location. Quiet neighborhood, clean, comfy beds and linens, and it looks just like the pictures. We walked to Model bakery in the mornings for their wonderful English muffins. Found a hidden gem tasting room called Hayfork right around the corner (behind Clif Family)that does free tastings on Fridays! Excellent wine! And of course we got in a burger at Gotts. The location makes it easy to walk to Main Street with lots of restaurants and shopping. There...
Stylish Condo Steps from St. Helena Wineries & Downtown
WorldMark Windsor - 1 Bedroom
Pool
WorldMark Windsor - 1 Bedroom
2.0 star property
9.0 out of 10, Wonderful, (2)
"The condo was very clean and had everything needed for a relaxing stay. The pool was also wonderful with no overcrowding! "
WorldMark Windsor - 1 Bedroom
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Exterior
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
WorldMark Windsor - 2 Bedroom Twin
Pool
WorldMark Windsor - 2 Bedroom Twin
2.0 star property
WorldMark Windsor - 2 Bedroom Twin
WorldMark Windsor - 2 Bedroom
Pool
WorldMark Windsor - 2 Bedroom
2.0 star property
9.4 out of 10, Exceptional, (3)
"Check-in was at 4:00 pm, but did not have a room ready until 5:20 pm. The room we were assigned had a patio area that backed to the roadway. Staff was accommodating and moved us to a second floor room, but we did not get into the room until after 6:00 pm. Overall we loved the property and had a very enjoyable stay. "
WorldMark Windsor - 2 Bedroom
Black Oak by Avantstay Modern & Chic Santa Rosa Hideaway With Pool Table, & Fire Pit
Interior
Black Oak by Avantstay Modern & Chic Santa Rosa Hideaway With Pool Table, & Fire Pit
3.5 star property
Black Oak by Avantstay Modern & Chic Santa Rosa Hideaway With Pool Table, & Fire Pit
Vino Blanco by Avantstay Private Wine Country Home w/ Mtn Views & Deck
House (4 Bedrooms) | Interior
Vino Blanco by Avantstay Private Wine Country Home w/ Mtn Views & Deck
3.5 star property
Vino Blanco by Avantstay Private Wine Country Home w/ Mtn Views & Deck
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
Interior
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
3.5 star property
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
Clementine By Avantstay Bright Modern Retreat w/ Pool, Pool Table & Large Patio
House (4 Bedrooms) | Interior
Clementine By Avantstay Bright Modern Retreat w/ Pool, Pool Table & Large Patio
3.5 star property
Clementine By Avantstay Bright Modern Retreat w/ Pool, Pool Table & Large Patio
Roomy Petaluma condo close to parks and shops
Fridge, microwave, oven, stovetop
Roomy Petaluma condo close to parks and shops
Roomy Petaluma condo close to parks and shops
Bennett Valley home is a great location to explore Sonoma Valley.
Exterior detail
Bennett Valley home is a great location to explore Sonoma Valley.
Bennett Valley home is a great location to explore Sonoma Valley.
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Private kitchen
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Don't see what you're looking for?
See all available properties in Windsor
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
Property grounds
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (88)
"Great house, no issues. "
Cottage home near the Russian River; county parks; numerous wineries
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Fridge, microwave, oven, stovetop
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
10.0 out of 10, Exceptional, (55)
"We had a wonderful stay. The property is gorgeous and the house was great for a group with places for everyone to be together or separate when needed. We only have a few recommendations. First, the driveway is quite steep and curvy. A caution on that especially if you drive a larger vehicle as we did. We never could get the hot tub to heat up, even after contacting the host. Instructions for that were not in the guest book. Even though the host walked us through it, having it written down would...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Oceanfront - Hot Tub - Newly Remodeled Cottage
Property grounds
Oceanfront - Hot Tub - Newly Remodeled Cottage
9.8 out of 10, Exceptional, (342)
"Breathtaking views and lovely house! Sunsets from the hot tub were my favorite!"
Oceanfront - Hot Tub - Newly Remodeled Cottage
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 condos in Windsor cost?
Condos in Windsor range from AU$840 to AU$840 per night. This gives you loads of room for your entire crew at a price that’s friendly on the pocket. This price was 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 condos are there in Windsor?
You’ll find 31 condos in Windsor. No matter if you’re taking a trip with the little ones or getting away with your buddies, Expedia can help you find the right space for your crew.
What is there to do in Windsor near my condo?
Windsor has enough experiences and activities to entertain you for weeks (or months!), beginning with Safari West. Russian River Vineyard, Luther Burbank Centre for the Arts and Kendall-Jackson Wine Estate and Gardens are other impressive attractions. If you’re in town a while, Mazzocco Winery and Matrix Winery are nice final touches to your itinerary.