Title: Book the Best BOUTIQUE Hotels in Windsor in 2025 | Expedia.ca

  

[Windsor Travel Guide](https://expedia.ca/Windsor.dx9542)[Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d9542.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d9542.Travel-Guide-VacationRentals)[Things to do in Windsor](https://expedia.ca/Things-To-Do-In-Windsor.d9542.Travel-Guide-Activities)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d9542.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d9542.Destination-Travel-Guides)

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# Find Boutique Hotels in Windsor, CA

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## Check availability on Windsor Boutique Hotels

Tonight

[Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9542&startDate=2025-10-18&endDate=2025-10-19&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=9542&startDate=2025-10-19&endDate=2025-10-20&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=9542&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=9542&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Windsor Boutique Hotels

![Exterior](https://images.trvl-media.com/lodging/2000000/1680000/1675800/1675737/c00a4336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1680000/1675800/1675737/34ff461b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 7:00 AM to 10:30 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/2000000/1680000/1675800/1675737/b9692dc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Tuscany Suite](https://images.trvl-media.com/lodging/2000000/1680000/1675800/1675737/827b5c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kenwood Inn and Spa

Kenwood

9.6/10

Exceptional

(688)

"Beautiful grounds, staff was super helpful and pleasant and our room was lovely. Very spacious, comfortable bed and it had a fire place. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cindy

CA $295

CA $401 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Glen-Ellen-Hotels-Kenwood-Inn-And-Spa.h1675737.Hotel-Information)

![Sundeck](https://images.trvl-media.com/lodging/2000000/1540000/1535500/1535453/6305e1ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe King](https://images.trvl-media.com/lodging/2000000/1540000/1535500/1535453/0e8e2bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1540000/1535500/1535453/a0eccba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/2000000/1540000/1535500/1535453/17e25357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Gaige House

Glen Ellen

9.2/10

Wonderful

(1003)

"Wonderful staff! Such a pleasant, beautiful, relaxing place to spend a night...or more! Wine tasting, breakfast, great location to restaurants, and Sonoma. Will definitely return."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elaine

CA $327

CA $421 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Glen-Ellen-Hotels-Gaige-House-Ryokan.h1535453.Hotel-Information)

![Suite | Balcony](https://images.trvl-media.com/lodging/7000000/6950000/6948900/6948841/ee043234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily full breakfast (USD 25 per person)](https://images.trvl-media.com/lodging/7000000/6950000/6948900/6948841/4e36bccb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive Room](https://images.trvl-media.com/lodging/7000000/6950000/6948900/6948841/62b85698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/7000000/6950000/6948900/6948841/c61aaa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grape Leaf Inn

Healdsburg

9.4/10

Exceptional

(161)

"I can’t say enough amazing things about Ve and the Grape Leaf Inn. Best hostess ever! She truly went above and beyond. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jessica

CA $373

CA $433 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Healdsburg-Hotels-Grape-Leaf-Inn.h6948841.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/790000/786900/786805/9d93bedd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/790000/786900/786805/38211be6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/790000/786900/786805/d4bf0fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hot tub, body treatments, aromatherapy, hot stone massages](https://images.trvl-media.com/lodging/1000000/790000/786900/786805/77b28c44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Healdsburg

Healdsburg

9.2/10

Wonderful

(424)

"Lovely hotel in the heart of Healdsburg. Wonderful stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Erica

CA $579

CA $746 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Healdsburg-Hotels-Hotel-Healdsburg.h786805.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/2000000/1640000/1639800/1639752/808f26c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1640000/1639800/1639752/9e796a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/2000000/1640000/1639800/1639752/75cedea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds (Mansion)](https://images.trvl-media.com/lodging/2000000/1640000/1639800/1639752/d3e96341.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 27 North

Healdsburg

9.6/10

Exceptional

(298)

"Great hotel in Healdsburg. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

PAMELA

CA $708

CA $880 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Healdsburg-Hotels-Hotel-Les-Mars.h1639752.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&regionId=9542&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true)

## Top Windsor Hotel Reviews

## Frequently asked questions

### What's there to see and do in Windsor?

> The wineries and restaurants are just some of the things to enjoy while you're in the area. Russian River, Windsor Golf Club, and Pacific Coast Air Museum are some of the local sights worth visiting. Some other things you might want to enjoy include Charles M. Schulz Museum, Healdsburg Museum, and Sonoma County Museum.

### What kind of weather should I plan for when I travel to Windsor?

> Understanding the weather in Windsor will help you enjoy your stay to the fullest. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are February and December with an average of 49°F. Average annual precipitation for Windsor is 28 inches.

### What's the best way to get to my boutique hotel in Windsor?

> You have a few options for getting to Windsor. The closest major airport is Santa Rosa, CA (STS-Sonoma County), which is located 2.6 mi (4.2 km) from the heart of the city. If you'd like to explore around the area, consider renting a car to take in more sights.

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