A stone bridge over a calm river, a historic tower, and illuminated buildings at dusk.

Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

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 CA $177
CA $1,085 total
includes taxes & fees
Sep 1 - Sep 2
Wildflower

2. 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.
The price is CA $1,169
CA $2,127 total
includes taxes & fees
Aug 9 - Aug 10
Elegant Vineyard Living at a Private Wine Country Estate

3. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (126 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is CA $155
CA $177 total
includes taxes & fees
Sep 7 - Sep 8
Wildhaven Sonoma Glamping

4. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.6 out of 10, Exceptional, (5 reviews)
"Nice camping spot "
United States
Evelyn
The price is CA $83
CA $94 total
includes taxes & fees
Aug 16 - Aug 17
The Ranch at Lake Sonoma

5. 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 CA $203
CA $572 total
includes taxes & fees
Aug 10 - Aug 11
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

6. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is CA $231
CA $518 total
includes taxes & fees
Aug 19 - Aug 20
Wine Country Cottage Escape

7. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (35 reviews)
"Very nice, extremely well equpped home. Very quiet with great nlback patio. Would defistay here again."
United States
Bill F.
The price is CA $231
CA $670 total
includes taxes & fees
Aug 31 - Sep 1
Somms Rest ⎮ Designed. Curated. Peaceful.

8. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (25 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is CA $183
CA $406 total
includes taxes & fees
Aug 21 - Aug 22
2 Hidden Wine Country Gem Upstairs Unit

9. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (40 reviews)
"Great hosts. Very accommodating. Clean and beautiful property. Great timely communication with hosts."
United States
Neeraj
The price is CA $252
CA $749 total
includes taxes & fees
Aug 31 - Sep 1
Serenity at the Russian River

10. 2BR Bungalow - Russian River & Wine Country

2BR Bungalow - Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (17 reviews)
"Had a great stay. Great host and location. Very quiet and relaxing. "
United States
Robert A.
The price is CA $253
CA $664 total
includes taxes & fees
Aug 9 - Aug 10
2BR Bungalow - Russian River & Wine Country

11. 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, (12 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
The price is CA $280
CA $612 total
includes taxes & fees
Aug 19 - Aug 20
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

12. Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (51 reviews)
"Very cute and luxurious!! We really enjoyed our stay and great proximity to downtown. "
United States
Yvonne L.
The price is CA $158
CA $461 total
includes taxes & fees
Aug 10 - Aug 11
Private Lofted Downtown Studio

13. Wine Country Getaway

Wine Country Getaway
Mirabel Heights
10.0 out of 10, Exceptional, (33 reviews)
"Everything was perfect and people in change of the hotel were incredible "
United States
dalton s.
The price is CA $278
CA $787 total
includes taxes & fees
Aug 24 - Aug 25
Wine Country Getaway

14. The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (62 reviews)
"Great little place to stay / perfect location in town close to everything / wonderful front patio "
United States
ANTHONY B.
The price is CA $172
CA $318 total
includes taxes & fees
Sep 1 - Sep 2
The Tiny Tipsy Turtle

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

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Northwest Santa Rosa
10.0 out of 10, Exceptional, (84 reviews)
"Awesome pet friendly home with nice backyard, great location. Really enjoyed our two night stay in this well appointed home while visiting surrounding areas. Cynthia responded so quickly to any of our questions. Would love to stay here again! "
United States
Keri S.
The price is CA $331
CA $768 total
includes taxes & fees
Aug 10 - Aug 11
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

16. 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 CA $364
CA $827 total
includes taxes & fees
Aug 12 - Aug 13
Russian River Brew-cation Home

17. 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 CA $271
CA $568 total
includes taxes & fees
Aug 10 - Aug 11
Peaceful, charming, cottage in wine country. Beautiful yard!

18. 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, (74 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is CA $404
CA $859 total
includes taxes & fees
Aug 17 - Aug 18
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

19. Relaxing Vineyard View, Rooftop Deck & Game Room

Relaxing Vineyard View, Rooftop Deck & Game Room
Sebastopol
10.0 out of 10, Exceptional, (24 reviews)
"The location was perfect if you enjoy the Russian River Wineries and the Healdsburg area. The house itself is full of charm and character. It was nice to be able to unwind with friends at the dining table and play cards after a collaboratively cooked meal. The little town of Graton has a couple of good little restaurants, too!"
United States
Jeff D.
The price is CA $227
CA $740 total
includes taxes & fees
Aug 12 - Aug 13
Relaxing Vineyard View, Rooftop Deck & Game Room

20. Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.0 out of 10, Wonderful, (6 reviews)
"Beautiful place. Bed was extremely comfortable. Overall environment was pleasant. Coffee set up was good for me as a black coffee drinker. We would stay again and would happily recommend it to others."
United States
Brad
The price is CA $228
CA $405 total
includes taxes & fees
Sep 1 - Sep 2
Sebastopol Lux Walk toTown Guest Suite
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

Find out more about Windsor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Dom Whitney Tasting Lounge, 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?

Bodega Bay - Sonoma Coastline: Visitors like this Windsor vacation home rental. It is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals are there in Windsor?

Choose from 31 Expedia vacation rentals in Windsor for a memorable vacation.

What can I see and do in Windsor?

Family-friendly attractions include Dom Whitney Tasting Lounge and Powell's Sweet Shoppe - Windsor, whereas Russian River is a spot to enjoy the outdoors. Windsor Golf Club and Pacific Coast Air Museum 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.