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!!

Guest favorite
Condo in Windsor
5 out of 5 average rating, 5 reviews

2 Separate 3BR Apts with Resort Amenities

These two separate 3-bedroom, 2-bath apartments transform a simple getaway into a shared family experience, giving everyone room to relax while still staying close. Together, they comfortably host up to 16 guests, making them perfect for group trips that need both togetherness and privacy. Enjoy the freedom of vacationing side by side while taking advantage of resort-style amenities: pools, hot tubs, a fitness center, volleyball and basketball courts, a kids’ play area, and a game center.

Superhost
Condo in Windsor

Windsor Resort @ Russian River Valley-3-Bd Suite

Come experience the Russian River Valley, one of California's most beautiful and distinctive wine regions. You'll experience an unforgettable vacation 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.

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)

A spacious swimming pool is surrounded by numerous lounge chairs under bright blue skies. Umbrellas provide shade along the poolside area, with well-maintained landscaping adding greenery in the background. The resort buildings are visible, offering a welcoming atmosphere for relaxation.
Condo in Windsor
4.74 out of 5 average rating, 27 reviews

WorldMark Windsor One-Bedroom Condo

Renowned for its wine, Sonoma is also one of the most scenic destinations in Northern California. Whale watching, fishing, kayaking and hiking are all popular activities in nearby Bodega Bay. In this spacious one-bedroom resort suite you will enjoy a king bed in the bedroom and one queen Murphy bed in the living room. Additional amenities include a full kitchen and dining area, gas fireplace, washer/dryer and a private terrace with gas barbecue. Maximum occupancy is four.

Top guest favorite
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, 121 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 favorite
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, 56 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, 97 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.

Superhost
Condo in Cobb
5 out of 5 average rating, 3 reviews

Rouge Cobb Mountain Hotel - Cabin 4

 Dog-Friendly Cabin | Wine Country Retreat | Scenic NorCal Savor the flavors of Northern California from this charming 1-bedroom, 1-bath cabin in Cobb. Nestled among the trees, it offers easy access to local wineries, hiking trails, golf courses and Clear Lake. After a day of wine tasting or outdoor adventures, relax on your private patio with a glass of local vino or enjoy a cozy night in with the 65” Smart TV.

Condo in Petaluma
New place to stay

Stylish 2BR/2BA Retreat in the Heart of Petaluma

Stylish 2BR/2BA apartment in the heart of Petaluma, perfect for a relaxing stay. Enjoy a bright, comfortable space with two bedrooms and two full bathrooms. Conveniently located near the highway and just 30 minutes from beautiful Bodega Bay. A shopping plaza with grocery stores and a fully equipped gym is just steps away, along with a jacuzzi on the premises and on-site parking for your ease.

Superhost
Condo in Cobb
4.8 out of 5 average rating, 10 reviews

Rouge Cobb Mountain Hotel - Cabin 2

 Dog-Friendly Cabin | Near Trails & Clear Lake Adventure awaits at this cozy 1-bedroom, 1-bath Middletown cabin! Start your day with coffee from a nearby café, then hit local hiking and biking trails, golf at Belmont Pines, or explore Clear Lake by boat. In the evening, unwind on your private patio with a glass of local wine under the shady umbrella.

Popular amenities for Windsor condo rentals

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$48,291 GYDG$47,664 GYDG$44,319 GYDG$41,601 GYDG$41,810 GYDG$45,155 GYDG$44,946 GYDG$44,528 GYDG$43,901 GYDG$51,218 GYDG$46,618 GYDG$45,991 GYD
Avg. temp10°C10°C11°C11°C12°C13°C14°C14°C15°C13°C12°C10°C

Quick stats about condo rentals in Windsor

  • Total vacation rentals

    Explore 120 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at G$14,634 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,540 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    120 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Windsor vacation rentals include wi-fi 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