Windsor Vacation Homes

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

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Our top choices for Windsor holiday homes

A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

1. Wildflower

Windsor

Keri S.

HK$6,995 total

includes taxes & fees

9 Sept - 10 Sept

A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

2. Elegant Vineyard Living at a Private Wine Country Estate

Windsor

Eric B.

HK$8,607 total

includes taxes & fees

7 Sept - 8 Sept

A house with a swimming pool, outdoor furniture, and a well-maintained garden.

3. Eastside Eden - Pool, Hot Tub and Tastings Included

Healdsburg

Dan M.

HK$14,141 total

includes taxes & fees

14 Sept - 15 Sept

A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

4. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Healdsburg

David S.

HK$3,617 total

includes taxes & fees

21 Sept - 22 Sept

A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

5. Wine Country Cottage Escape

Fulton

HK$2,874 total

includes taxes & fees

8 Sept - 9 Sept

6. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Northwest Santa Rosa

kevin c.

HK$3,214 total

includes taxes & fees

14 Sept - 15 Sept

A spacious living area with a high ceiling, a large window, and a cozy seating arrangement.

7. Forestville Redwood Escape

Forestville

HK$3,081 total

includes taxes & fees

28 Sept - 29 Sept

A deck with outdoor seating, a grill, and a view of a house with large windows.

8. Somms Rest ⎮ Designed. Curated. Peaceful.

Mirabel Heights

Jana P.

HK$3,999 total

includes taxes & fees

16 Sept - 17 Sept

A modern living room with a blue sectional sofa, a wooden coffee table, and a staircase leading to another room.

9. Serenity at the Russian River

Mirabel Heights

Neeraj

HK$4,231 total

includes taxes & fees

7 Sept - 8 Sept

An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

10. Peaceful, charming, cottage in wine country. Beautiful yard!

Sebastopol

Mikaela

HK$2,712 total

includes taxes & fees

8 Sept - 9 Sept

A swimming pool with a slide, a barbecue area, and a wooden deck.

11. 2 Hidden Wine Country Gem Upstairs Unit

Scenic Brush Creek

Glen M.

HK$2,107 total

includes taxes & fees

13 Sept - 14 Sept

An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

12. Russian River Brew-cation Home

Northwest Santa Rosa

Gina N.

HK$3,993 total

includes taxes & fees

7 Sept - 8 Sept

A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

13. Wine Country Getaway

Mirabel Heights

Rachel S.

HK$4,412 total

includes taxes & fees

7 Sept - 8 Sept

A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

14. The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

Forestville

Nick C.

HK$3,302 total

includes taxes & fees

6 Oct - 7 Oct

A modern kitchen with white cabinets, a central island, and a dining area with a round table and chairs.

15. Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

Northwest Santa Rosa

Avani S.

HK$4,170 total

includes taxes & fees

7 Sept - 8 Sept

A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

16. Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Northwest Santa Rosa

Nancy P.

HK$5,333 total

includes taxes & fees

7 Sept - 8 Sept

A wooden interior with a dining area, a bench, and a mirror on the wall.

17. Cozy Riverfront Cabin - Beach Access & Wood Stove

Guerneville

Jehanne H.

HK$4,356 total

includes taxes & fees

20 Sept - 21 Sept

A living room with a wooden dining table set for four, a black sofa, and a small coffee table.

18. Charming Wine Country Home w/Hot Tub near Downtown

Santa Rosa

Steve S.

HK$3,877 total

includes taxes & fees

7 Sept - 8 Sept

A spacious living area with a wooden ceiling, a sofa, a coffee table, and a kitchen in the background.

19. Walk to Downtown Sebastopol * Luxe Vacation Living

Sebastopol

Courtney E.

HK$2,991 total

includes taxes & fees

16 Sept - 17 Sept

A two-story house with a swimming pool, outdoor seating, and a staircase leading to the upper level.

20. Farpoint: Heated Infinity Pool, Mountain Views

Santa Rosa

Vanessa R.

HK$7,715 total

includes taxes & fees

7 Sept - 8 Sept

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Top Windsor Hotel Reviews

The Inn at the Tides

10/10 Excellent

"We had a lovely room at the Tides. Service was friendly and attentive."

Vinarosa Resort & Spa

10/10 Excellent

"Beautiful hotel! The entire staff was wonderful and clearly had customer service as their first priority. Anything we needed was attended to promptly. We lounged by the pool, got spa services (which were amazing) and sat out until late at night on our terrace! The hotel is convenient to Healdsburg, Santa Rosa and the Redwood parks. We loved the location and the fact that things were convenient, but not right outside the hotel. We also had a lot of fun in the “secret” pool room!"

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