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

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Windsor vacation rentals

Property grounds

1. Wildflower

Wildflower
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is SAR 1,266
SAR 3,989 total
includes taxes & fees
13 Oct - 14 Oct
Wildflower
Outdoor pool, a heated pool

2. Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg

Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Healdsburg
9.6 out of 10, Exceptional, (193 reviews)
"Great location and cozy home."
United States
Kelly B.
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Dining

3. Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
Elegant Vineyard Living at a Private Wine Country Estate
Pool

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

Eastside Eden - Pool, Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (5 reviews)
"This is a great location with wonderful outdoor space and nice layout of the home. A perfect spot for a long weekend or longer. Great views on the wrap around deck. Would definitely come back. "
United States
Dan M.
Eastside Eden - Pool, Hot Tub and Tastings Included
Deluxe Cabin, 1 Queen Bed, Patio, Garden View | Laptop workspace, WiFi (free), bed sheets

5. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (133 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is SAR 378
SAR 430 total
includes taxes & fees
27 Sep - 28 Sep
Wildhaven Sonoma Glamping
Terrace/patio

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

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 reviews)
"Great location!"
United States
Riley F.
The price is SAR 659
SAR 1,477 total
includes taxes & fees
30 Sep - 1 Oct
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Coffee/tea maker, fridge, microwave, oven

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

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
The price is SAR 436
SAR 1,388 total
includes taxes & fees
29 Sep - 30 Sep
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Smart TV

8. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (41 reviews)
"We had a great stay. The house was clean, the beds were comfy and a very convenient location. Just wish there was an ironing board. I would definitely recommend staying here."
United States
Patricia A.
The price is SAR 676
SAR 2,027 total
includes taxes & fees
27 Sep - 28 Sep
Serenity at the Russian River
Terrace/patio

9. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (36 reviews)
"Great stay, highly recommend!"
United States
Jana P.
The price is SAR 710
SAR 1,916 total
includes taxes & fees
6 Oct - 7 Oct
Somms Rest ⎮ Designed. Curated. Peaceful.
Dining

10. Wine Country Getaway

Wine Country Getaway
Mirabel Heights
10.0 out of 10, Exceptional, (33 reviews)
"Great place, would stay again!"
United States
Rachel S.
The price is SAR 744
SAR 2,038 total
includes taxes & fees
28 Sep - 29 Sep
Wine Country Getaway
Outdoor dining

11. Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"What a perfect place to stay for a wine country weekend! We’ll definitely be back!"
United States
Gina N.
The price is SAR 759
SAR 1,916 total
includes taxes & fees
28 Sep - 29 Sep
Russian River Brew-cation Home
Dining

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

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
10.0 out of 10, Exceptional, (15 reviews)
"Nice place, great location, had everything we needed. Helpful and prompt communication by the host. This was a great base for exploring the area."
United States
Rebecca I.
The price is SAR 714
SAR 1,684 total
includes taxes & fees
28 Sep - 29 Sep
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
2 bedrooms, desk, iron/ironing board, WiFi (free)

13. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (79 reviews)
"Lovely vacation rental"
United States
suzanne g.
The price is SAR 751
SAR 1,577 total
includes taxes & fees
1 Oct - 2 Oct
Wine Country Cottage in downtown Santa Rosa, CA
Outdoor dining

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

Peaceful, charming, cottage in wine country. Beautiful yard!
Sebastopol
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful, charming cottage in a quiet neighborhood. Close to wineries and food."
United States
Mikaela
The price is SAR 538
SAR 1,280 total
includes taxes & fees
28 Sep - 29 Sep
Peaceful, charming, cottage in wine country. Beautiful yard!
Property grounds

15. Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (53 reviews)
"Very cute and luxurious!! We really enjoyed our stay and great proximity to downtown. "
United States
Yvonne L.
The price is SAR 896
SAR 1,769 total
includes taxes & fees
5 Oct - 6 Oct
Private Lofted Downtown Studio
TV, fireplace

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

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (76 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is SAR 1,303
SAR 2,558 total
includes taxes & fees
27 Sep - 28 Sep
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Beach

17. The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (66 reviews)
"Great little place to stay / perfect location in town close to everything / wonderful front patio "
United States
ANTHONY B.
The price is SAR 387
SAR 764 total
includes taxes & fees
30 Sep - 1 Oct
The Tiny Tipsy Turtle
Exterior

18. Rivers Breeze - Wine Tastings Included

Rivers Breeze - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (20 reviews)
"Lovely place, exactly as described. Really nice place to sit & listen to nature, access to river, well-appointed, easy, and the owners are responsive and easy to work with."
United States
Seppo H.
The price is SAR 1,241
SAR 3,501 total
includes taxes & fees
28 Sep - 29 Sep
Rivers Breeze - Wine Tastings Included
Outdoor pool, a heated pool

19. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful stay!"
United States
Adam C.
The price is SAR 1,183
SAR 1,341 total
includes taxes & fees
28 Sep - 29 Sep
Cozy Wine Country Guesthouse with Private Pool & Yard
Outdoor dining

20. Redwood Riverfront - Hot Tub and Tastings Included

Redwood Riverfront - Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (69 reviews)
"We had a decent stay at Riverfront. Having the house by the river was pleasant. We were a bit disappointed to find that the hot tub was below the deck and we couldnt use it at night since there seem to be no outdoor light. Overall it was nice secluded stay."
United States
Kenneth M.
The price is SAR 1,892
SAR 4,217 total
includes taxes & fees
6 Oct - 7 Oct
Redwood Riverfront - Hot Tub and Tastings Included
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

The Inn at the Tides

The Inn at the Tides

10/10 Excellent
"3rd time staying here. Really nice, spacious rooms with a fireplace. Fairly quiet. Nice views from some rooms. Beautiful big pool, jacuzzi and sauna. Breakfast across the road is good, and lovely restaurant on the Bay too. Highly recommend"
Pamela 2-night trip
Posted 8 hours ago
The Inn at the Tides

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.