A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

Windsor Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Windsor vacation rentals

A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

1. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (140 reviews)
"Awesome place to stay . So fun"
United States
Amy
$107 nightly
The price is $122
Dec 15 - Dec 16
Total with taxes and fees
Wildhaven Sonoma Glamping
A room with a brown sofa, two wicker chairs, a small table, and a lamp.

2. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
8.0 out of 10, Very good, (3 reviews)
"Stayed in one of the cottages. The little house was clean, had an older style kitchen and bathroom, but the bed was great. It isn't fancy, but it was just a nice stay. The grounds are pretty and it was quiet."
United States
Rory
$213 nightly
The price is $244
Nov 22 - Nov 23
Total with taxes and fees
Hideaway Cottages
A single-story cabin with a small porch, situated on a hillside overlooking a body of water and mountains.

3. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed my stay"
United States
Epeli
$79 nightly
The price is $90
Nov 15 - Nov 16
Total with taxes and fees
The Ranch at Lake Sonoma
A bedroom with a bed, a small table, and a chair, a bathroom with a sink and a mirror, and a sliding glass door leading to an outdoor area.

4. Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.8 out of 10, Excellent, (39 reviews)
"Waterfront cabins were amazing. The location and wildlife were serene, fantastic place to stay."
United States
Carmino
$149 nightly
The price is $166
Dec 15 - Dec 16
Total with taxes and fees
Mandala Springs Wellness Retreat Center
A modern kitchen with wooden cabinets, stainless steel appliances, and a glass door refrigerator.

5. Private Pool & Large Deck: Modern Cotati Villa!

Private Pool & Large Deck: Modern Cotati Villa!
4.0 star property
Cotati
$970 nightly
The price is $1,106
Nov 15 - Nov 16
Total with taxes and fees
Private Pool & Large Deck: Modern Cotati Villa!
A spacious living area with a sectional sofa, a blue armchair, and a dining table.

6. Dog-friendly Haven w/ Stunning Views in Bodega Bay

Dog-friendly Haven w/ Stunning Views in Bodega Bay
3.0 star property
Bodega Bay
$848 nightly
The price is $967
Nov 18 - Nov 19
Total with taxes and fees
Dog-friendly Haven w/ Stunning Views in Bodega Bay
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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Top Windsor Hotel Reviews

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

8/10 Good
"The best aspect of Dry Creek Inn is its location. Right of Hwy 101 and only about 5 minutes from downtown Healdsburg. Although close to the street, it really was fairly quiet. Easy access in and out. Rooms were cleaned and serviced daily, Rooms are not updated, but I found them clean and roomy. Great coffee shop (Plank Coffee) and grocery market (Big Johns) just a short walk away. Compared to other hotels nearby, charging 300+ per night, it is a real bargain. I would definitely stay here again."
Daniel 4-night trip
Posted 9 hours ago
Dry Creek Inn MOD Collection by Sonesta

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Powell's Sweet Shoppe - Windsor, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers say Windsor has a good selection of top-notch restaurants and wineries. Make sure you have time to check out the festivals while you're in the area.

What's the top vacation rental that Windsor has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: Visitors like this Windsor vacation home rental. It is located on the waterfront and has a balcony, a selection of books, and a Smart TV to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Windsor?

Choose from 30 Expedia vacation rentals in Windsor for a memorable vacation.

What can I see and do in Windsor?

Cultural attractions include Pacific Coast Air Museum, whereas Russian River is a spot to enjoy nature. Windsor Golf Club and Windsor Oaks Vineyards are other places to visit while you're in town.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a small group gathering.