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Search Vacation Homes in Windsor

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Browse Select Windsor Vacation Homes

Beautiful 3 Bedroom 2 Bath Wine Country Home With a Fire Pit & BBQ
Situated in Windsor, this golf vacation home is 1.3 mi (2.1 km) from Windsor Golf Club and 2.6 mi (4.2 km) from Pacific Coast Air Museum. Russian River and Kendall-Jackson ...
4.9/5Exceptional! (11 reviews)
Wonderful stay
"The home was welcoming had everything we needed."

Reviewed on Jul 27, 2021

Beautiful 3 Bedroom 2 Bath Wine Country Home With a Fire Pit & BBQ
Luxury Modern Farmhouse With Pool, Spa and Peloton
This family-friendly Windsor vacation home is located in a rural location, within 3 mi (5 km) of Russian River and Windsor Golf Club. Pacific Coast Air Museum ...
5/5Exceptional! (17 reviews)
Fantastic
"We had a great experience with three generations. The property has everything you need. Gorgeous setting with lots of seating areas, a fantastic pool, a kitchen with everything we needed (and mor), and a perfect kids room. Windsor is a cute town with a few parks and a nice farmers market. Already ..."

Reviewed on Jun 16, 2021

Luxury Modern Farmhouse With Pool, Spa and Peloton
Oak Leaf Retreat - 5 Acres, Spa & Vineyards! Peaceful
Located in a rural location, this family-friendly vacation home is within 6 mi (10 km) of Windsor Oaks Vineyards, Windsor Golf Club, and Healdsburg Golf Club. ...
4.9/5Exceptional! (36 reviews)
Wonderful weekend
"We were four couples in the area for a wedding, and had a wonderful time at this beautiful house. The setting is lovely, with a huge lawn surrounded by vineyards. The house was comfortable and clean, and had everything we could ask for. Perfect for a family and/or friends weekend in the wine country. ..."

Reviewed on Jun 26, 2019

Oak Leaf Retreat - 5 Acres, Spa & Vineyards! Peaceful
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The Eastside - Healdsburg - 3 Br Home
3.5 out of 5
11306 Eastside Road, Windsor, CA
Situated in Windsor, this vacation home is 0.9 mi (1.5 km) from Russian River and 2.9 mi (4.7 km) from Pezzi King Winery. Healdsburg Plaza and Healdsburg Center ...
The Eastside - Healdsburg - 3 Br Home
Elegant Creek-side W/ Deck & Private Hot Tub 4 Bedroom Home
3.5 out of 5
9746 Brooks Rd S, Windsor, CA
Situated in Windsor, this vacation home is 2.2 mi (3.5 km) from Windsor Oaks Vineyards and within 6 mi (10 km) of Windsor Golf Club and Pezzi King Winery. Kendall-Jackson ...
Elegant Creek-side W/ Deck & Private Hot Tub 4 Bedroom Home
Historic Queen Anne Victorian in the Heart of Windsor
Set in the center of Windsor, this family-friendly vacation home is 2.5 mi (4 km) from Windsor Golf Club, and within 6 mi (10 km) of Pacific Coast Air Museum ...
5/5Exceptional! (10 reviews)
Perfect wedding getaway!
"This property was perfect for our needs! It was quaint and very clean! It was well-stocked and extremely comfortable! It was close in proximity to many restaurants and markets. We will definitely keep this property in mind for future visits!"

Reviewed on Jun 14, 2021

Historic Queen Anne Victorian in the Heart of Windsor
Healdsburg, 5br/3.5ba Estate, Hot Tub, Bocce Court
Located in Windsor, this family-friendly vacation home is 0.7 mi (1.2 km) from Russian River, and within 6 mi (10 km) of Windsor Golf Club and Healdsburg Golf ...
4.2/5Very Good! (5 reviews)
Birthday Celebrations
"Our family met in the area to celebrate milestone birthdays. This house was perfect for our family dinners and relaxing!!"

Reviewed on Jun 29, 2021

Healdsburg, 5br/3.5ba Estate, Hot Tub, Bocce Court
Windsor Home on Golf Course
Situated in Windsor, this golf vacation home is 0.3 mi (0.6 km) from Windsor Golf Club and 1.7 mi (2.7 km) from Pacific Coast Air Museum. Kendall-Jackson Wine ...
5/5Exceptional! (6 reviews)
Great allocation and responsive host
"We had a great experience at this property. We had one small issue with the electricity and the owner came within minutes and fixed it! Would recommend!"

Reviewed on Jul 21, 2021

Windsor Home on Golf Course
Healdsburg 4br/3ba Home W/vineyard Views
This family-friendly Windsor vacation home is located in a rural location, 0.8 mi (1.3 km) from Russian River, and within 6 mi (10 km) of Windsor Golf Club and ...
4.6/5Exceptional! (21 reviews)
Fantastic house and location.
"We had a phenomenal time staying at this property. Hosts were responsive when we need extra things. Would absolutely return."

Reviewed on Jun 26, 2021

Healdsburg 4br/3ba Home W/vineyard Views
New Listing! Wine Country W/ Pool & Hot Tub 4 Bedroom Home
3.5 out of 5
10934 Eastside Rd, Windsor, CA
Situated in Windsor, this golf vacation home is within 6 mi (10 km) of Pezzi King Winery, Healdsburg Plaza, and Healdsburg Center for the Arts. Raven Performing ...
New Listing! Wine Country W/ Pool & Hot Tub 4 Bedroom Home
3 bed 2 Bath 1 Mile From Windsor Town Green
This family-friendly vacation home is located in the city center, within 3 mi (5 km) of Windsor Golf Club and Pacific Coast Air Museum. Russian River and Luther ...
5/5Exceptional! (2 reviews)
Wine County trip
"The owner was helpful with answering our questions and quick to respond. The home was close to many wineries and easy to locate as well as clean. We are planning another trip in March and will definitely be staying at this property again."

Reviewed on May 31, 2021

3 bed 2 Bath 1 Mile From Windsor Town Green
Windsor by Grand Vacations
1251 Shiloh Rd, Windsor, CA
Situated in Windsor, this vacation home is 0.2 mi (0.3 km) from Windsor Golf Club and 1.7 mi (2.7 km) from Pacific Coast Air Museum. Kendall-Jackson Wine Estate ...
Windsor by Grand Vacations
3br/2.5ba Furnished Townhouse Walk To Town Green
Located in the heart of Windsor, this vacation home is 2.4 mi (3.9 km) from Windsor Golf Club and within 6 mi (10 km) of Windsor Oaks Vineyards and Kendall-Jackson ...
3.3/5 (3 reviews)
Very nice place in Windsor with 1 issue
"I rented this town-home for 6 weeds in July & August while preparing my business to re-open during the pandemic. 1. The house is very spacious, comfortable and well stocked. The kitchen has everything you need. They have some great pots an pans if you are into that sort of thing (I am). 2.The house ..."

Reviewed on Aug 10, 2020

3br/2.5ba Furnished Townhouse Walk To Town Green
Estrella - Secluded Spanish-style Estate on 7 Acres of Vineyards
Situated in Windsor, this vacation home is 2.3 mi (3.6 km) from Windsor Golf Club and 2.5 mi (4.1 km) from Russian River. Pacific Coast Air Museum and Windsor ...
Estrella - Secluded Spanish-style Estate on 7 Acres of Vineyards
Relaxing Comfortable 3 Bedroom
Situated in Windsor, this vacation home is 2.7 mi (4.3 km) from Windsor Oaks Vineyards and within 6 mi (10 km) of Windsor Golf Club and Kendall-Jackson Wine ...
Relaxing Comfortable 3 Bedroom
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
Situated in Windsor, this vacation home is 2.3 mi (3.6 km) from Windsor Golf Club and 2.5 mi (4.1 km) from Russian River. Pacific Coast Air Museum and Windsor ...
3.5/5Good! (2 reviews)
Loved the property
"Really good home if you want to spend time with group of friends or family."

Reviewed on Feb 21, 2021

Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
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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.

Other property types in Windsor

Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 out of 5
8937 Brooks Road South, Windsor, CA
The price is $167 per night from Aug 31 to Aug 31
4.5/5Wonderful! (979 reviews)
"Lovely experience. Would return in a heartbeat!"

Reviewed on Jul 24, 2021

Hampton Inn & Suites Windsor - Sonoma Wine Country
Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

2.5 out of 5
8865 Conde Lane, Windsor, CA
The price is $142 per night from Sep 2 to Sep 2
4.3/5Excellent! (626 reviews)
"Great stay- despite being a smaller property everything was great- including breakfast and staff who were helpful and nice."

Reviewed on Jul 24, 2021

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel
WorldMark Windsor

WorldMark Windsor

3 out of 5
1251 Shilo Rd, Windsor, CA
4.6/5Exceptional! (258 reviews)
"The property was excellent. Check-in slightly longer than expected, but there was a pandemic and everyone wanted to get out. Had a great time and WorldMark Windsor made it happen."

Reviewed on May 1, 2021

WorldMark 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.

Booking Tips to Find the Best Windsor Vacation Homes


How much does it cost to rent a vacation home in Windsor?

You can find incredible Windsor vacation homes for all types of budgets: between $142 and $167 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Windsor?

If you are looking for a great deal on your vacation home in Windsor, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Windsor?

There are 20 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Windsor?

Begin by entering your trip dates to see what type of Windsor rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Windsor?

Booking Windsor vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Windsor rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Windsor along with your vacation property, into a Windsor vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

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