Condo vacation rentals in Windsor

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Top-rated condo rentals in Windsor

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A spacious outdoor pool is surrounded by loungers under shade umbrellas. The adjacent buildings feature balconies and well-maintained greenery. Blue skies and fluffy clouds add to the inviting atmosphere of the resort.
Condo in Windsor
4.5 out of 5 average rating, 4 reviews

2Bdm Condo Windsor WM Resort#4

Greetings from Windsor, California, located in the heart of Sonoma County's Russian River Valley. Whether you're here for the wine, fine dining, golf, scenery or to relax, you're sure to fall in love with the beautiful WorldMark Windsor resort. WorldMark Windsor is located on 10 acres with multiple three-story buildings, all with elevators. This resort consists of 228 studio, one-, two- and three-bedroom units, as well as three-bedroom penthouses, all with a fully equipped kitchen, air conditioning and a small balcony or patio with a gas barbecue.

A spacious pool area features a large, clear water swimming pool surrounded by lounge chairs and umbrellas. The adjacent building showcases multiple balconies and staircases, enhancing the inviting atmosphere of the resort.
Condo in Windsor

1 BR Worldmark Windsor Resort Condo Wine Country

Savor the sweetness of Sonoma. Whether it's your first visit to wine country or a frequent destination, you'll feel right at home at this resort nestled in the heart of Sonoma County. Swirl and sip varietals from local wineries with a perfectly paired charcuterie board until the sun goes down, then enjoy a scenic stroll through Old Downtown. Great Location in Windsor near Wine Country and Golf Course Area is untouched by fires, great place to stay for getaways, prime weekends, events, Golf!!

A three-story building is framed by lush greenery, featuring multiple balconies that overlook the expansive lawn. The architecture includes white railings and gabled roofs, creating a harmonious blend with the surrounding landscape.
Condo in Windsor
4.84 out of 5 average rating, 57 reviews

WorldMark Windsor, CA

The WorldMark Windsor resort is nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the newly constructed Old Downtown, a development that brings to life Windsor's past, including the old general store and meat market. Lively restaurants abound, and the Town Green also hosts a Sunday Farmers' Market and concerts on summer nights. (See more below)

Top guest favourite
A private patio features a swinging egg chair, capable of seating at least two people, surrounded by lush bamboo and a grassy area. Outdoor lights can be seen, complementing the serene atmosphere, while a pyramid heater provides warmth for cooler evenings.
Condo in Napa
4.99 out of 5 average rating, 100 reviews

Spacious&PeacefulOasis!Beautiful!PerfectlyLocated!

✨✨ Welcome to Your Modern Napa Stay! ✨✨ Discover the perfect blend of luxury and comfort in our stunning 2 bed, 2 bath spacious space. This contemporary retreat features stylish decor, an open-concept living space, ideal for relaxing after a day of exploring the beautiful wineries and vibrant culinary scene. Whether you're here for a romantic getaway, a trip with friends, or a family vacay, our modern Napa retreat offers everything you need for a memorable stay!

Guest favourite
A well-appointed bedroom features a spacious bed with a neutral-colored headboard. A decorative pillow rests at the center of the bed. Two bedside tables with lamps are positioned beside the bed, and a window allows natural light to brighten the room.
Condo in Windsor
4.89 out of 5 average rating, 53 reviews

Sip, Taste, Hot Tub - Repeat - 2 Bdrm Condo-Slps 6

**New for 2026: zero housekeeping fees, just great stays.** Make this spacious condo in beautiful Sonoma Wine Country your home base. This two bedroom / two bath condo is well appointed with everything you’ll need to have a memorable getaway. Just minutes from Sonoma County’s world-class wineries, restaurants, shopping, and outdoor adventures. Guests have full access to all resort amenities including pools, spas, and on-site recreation areas.

Superhost
A comfortable sofa sits against a light blue wall, adorned with decorative cushions featuring intricate patterns. A small lamp stands beside it, providing ambient lighting. In the background, a well-equipped kitchen is visible, featuring wooden cabinetry and modern appliances.
Condo in Windsor
4.93 out of 5 average rating, 96 reviews

Resort Living w/ Pools - 2 Bdm Condo Slps 6

**New for 2026: zero housekeeping fees, just great stays.** Make this spacious condo in beautiful Sonoma Wine Country your home base. This two bedroom / two bath condo is well appointed with everything you’ll need to have a memorable getaway. Just minutes from Sonoma County’s world-class wineries, restaurants, shopping, and outdoor adventures. Guests have full access to all resort amenities including pools, spas, and on-site recreation areas.

Top guest favourite
Private room in Petaluma
4.89 out of 5 average rating, 225 reviews

Fine Accommodations by the river!

Incredible 14 year new commercial loft for your getaway w/private bedroom and bath! You'll be staying close to the Petaluma river with kayakers paddling by. Your room is on the 3rd level, so please be good w/stairs. There are hand railings along the stairs. New bed and fine supima cotton sheets with a down comforter! Coffee and tea are provided, along with a microwave, kettle, filtered water and a small refrigerator. Wifi available.

Superhost
Condo in Windsor

Windsor, CA. - Windsor Resort - 3-Bd

You'll experience an unforgettable vacation at Windsor Resort. Filled with family-owned wineries, gorgeous ocean hikes, magnificent groves of Redwood trees, and much more. This endearing city will entrance and excite all your senses to the point of you falling in love with this destination. With so many exciting things to do and extraordinary sights to take in, and leaving may become nearly impossible.

Superhost
Condo in Windsor

Windsor, CA, 3-Bedrm Dlx Z #1

3-NIGHT MINIMUM. 1-NIGHT IS OKAY -IF- YOUR BOOKING REQUEST IS WITHIN 72-HOURS OF YOUR STAY DATE ALSO = I can accept a 1-night stay for a weekend night (Friday or Saturday) if the date is within 2 days of stay date. 3-Bedroom Deluxe: King in master, queen in second, twins in third, queen Murphy bed in living. Maximum occupancy 8. *** Please review ALL details in each section ***

Superhost
A large outdoor pool is surrounded by neatly arranged lounge chairs and umbrellas. Lush greenery and multiple buildings are visible in the background under a clear blue sky, providing a spacious and relaxing environment for guests.
Condo in Windsor
5 out of 5 average rating, 3 reviews

Windsor, CA, 3 Bedroom Deluxe #2

3-NIGHT MINIMUM. 1-NIGHT IS OKAY -IF- YOUR BOOKING REQUEST IS WITHIN 72-HOURS OF YOUR STAY DATE ALSO = I can accept a 1-night stay for a weekend night (Friday or Saturday) if the date is within 2 days of stay date. Three Bedroom Deluxe: King in master, queen in second bedroom, twins in third bedroom, queen Murphy bed in living area. Maximum occupancy 8.

Superhost
A spacious outdoor swimming pool is surrounded by lounge chairs and sun umbrellas. Lush greenery and well-maintained landscaping frame the pool area, with multi-story resort buildings visible in the background under a clear blue sky.
Condo in Windsor
4.93 out of 5 average rating, 29 reviews

Windsor, CA, 2 Bedroom Queen #1

3-NIGHT MINIMUM. 1-NIGHT IS OKAY -IF- YOUR BOOKING REQUEST IS WITHIN 72-HOURS OF YOUR STAY DATE ALSO = I can accept a 1-night stay for a weekend night (Friday or Saturday) if the date is within 2 days of stay date. Two Bedroom: King in master, queen in second bedroom, queen Murphy bed in living area. Maximum occupancy 6.

Guest favourite
The exterior of a multi-level resort building is shown, featuring a blend of wood and stucco design. Spacious balconies and porches are visible on upper and lower levels. Lush green lawns surround the property, with pathways leading to the entrance.
Condo in Windsor
5 out of 5 average rating, 5 reviews

Windsor Resort 2bdr Queen

ALL GUEST MUST READ AND AGREE TO GUEST CONTRACT OR RESERVATIONS WILL BE SUBJECT TO CANCELLATION BY OWNER Please send the full name of the person checking in, as on the ID that will be shown when making your booking request. 6 Guest Max Kitchen: Full Beds: King Bed - 1,Queen Murphy Bed - 1,Varies Baths: 2

Popular amenities for Windsor condo rentals

When is the best time to visit Windsor?

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Avg. price$310 CAD$306 CAD$282 CAD$273 CAD$274 CAD$296 CAD$295 CAD$292 CAD$288 CAD$336 CAD$306 CAD$302 CAD
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Quick stats about condo rentals in Windsor

  • Total vacation rentals

    Explore 130 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at $96 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,620 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space and kid-friendly amenities

  • Vacation rentals with a pool

    130 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    130 of Windsor vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor rentals

  • 4.9 Average rating

    Windsor stays are highly rated by guests—averaging 4.9 out of 5!

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Windsor
  6. Condo rentals