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Our top choices for Windsor holiday homes
1. Sauna, Cold Plunge & Fire Pit Near Wineries
Sauna, Cold Plunge & Fire Pit Near WineriesWindsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
Keri S.
The price is HK$1,671
HK$7,547 total
includes taxes & fees
16 Nov - 17 Nov
2. Elegant Vineyard Living at a Private Wine Country Estate
Elegant Vineyard Living at a Private Wine Country EstateWindsor
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."
Eric B.
The price is HK$2,784
HK$7,440 total
includes taxes & fees
7 Dec - 8 Dec
3. Eastside Eden - Pool, Hot Tub and Tastings Included
Eastside Eden - Pool, Hot Tub and Tastings IncludedHealdsburg
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. "
Dan M.
4. Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Vineyard View Retreat • Fire Pit • Wine Tasting PerksHealdsburg
9.8 out of 10, Exceptional, (19 reviews)
"Great place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
Mark R.
The price is HK$1,306
HK$2,983 total
includes taxes & fees
1 Dec - 2 Dec
5. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Sonoma Wine Country Retreat | Near Top Wineries + Cozy EscapeNorthwest Santa Rosa
9.4 out of 10, Exceptional, (24 reviews)
"very nice space "
kevin c.
The price is HK$949
HK$2,827 total
includes taxes & fees
9 Dec - 10 Dec
6. Forestville Redwood Escape
Forestville Redwood EscapeForestville
The price is HK$1,122
HK$3,013 total
includes taxes & fees
2 Dec - 3 Dec
7. Wine Country Cottage Escape
Wine Country Cottage EscapeFulton
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! The area is beautiful, peaceful and quiet. The house is clean, well maintained and equipped. Really enjoyed it and look forward to our next visit."
Tina A.
The price is HK$1,294
HK$2,789 total
includes taxes & fees
16 Nov - 17 Nov
8. 2BR Bungalow - Russian River & Wine Country
2BR Bungalow - Russian River & Wine CountryForestville
9.8 out of 10, Exceptional, (22 reviews)
"Nice clean relaxing place to stay near the river! Was perfect for our little weekend getaway."
Greg K.
The price is HK$1,166
HK$3,207 total
includes taxes & fees
12 Nov - 13 Nov
9. Somms Rest ⎮ Designed. Curated. Peaceful.
Somms Rest ⎮ Designed. Curated. Peaceful.Mirabel Heights
9.8 out of 10, Exceptional, (38 reviews)
"Great stay, highly recommend!"
Jana P.
The price is HK$1,928
HK$4,249 total
includes taxes & fees
12 Dec - 13 Dec
10. Serenity at the Russian River
Serenity at the Russian RiverMirabel Heights
10.0 out of 10, Exceptional, (44 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."
Patricia A.
The price is HK$1,412
HK$4,036 total
includes taxes & fees
12 Nov - 13 Nov
11. The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
The Cozy Pine Cone . Hot tub- Deck & Grill ForestvilleForestville
10.0 out of 10, Exceptional, (16 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."
Rebecca I.
The price is HK$1,476
HK$3,446 total
includes taxes & fees
12 Nov - 13 Nov
12. 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)
"Great stay and location!"
Brandi K.
The price is HK$1,101
HK$2,470 total
includes taxes & fees
16 Nov - 17 Nov
13. 2 Hidden Wine Country Gem Upstairs Unit
2 Hidden Wine Country Gem Upstairs UnitScenic Brush Creek
9.8 out of 10, Exceptional, (32 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
Glen M.
The price is HK$981
HK$2,117 total
includes taxes & fees
17 Nov - 18 Nov
14. Russian River Brew-cation Home
Russian River Brew-cation HomeNorthwest 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!"
Gina N.
The price is HK$1,608
HK$3,895 total
includes taxes & fees
16 Nov - 17 Nov
15. Cozy Riverfront Cabin - Beach Access & Wood Stove
Cozy Riverfront Cabin - Beach Access & Wood StoveGuerneville
9.8 out of 10, Exceptional, (30 reviews)
"Our favorite place we have stayed in at the Russian river by FAR! Wonderful lakeside cabin feel. It feels like people have actually lived there and loved the home (unlike most rental properties that have clearly never had a resident). Great location right by downtown."
Savannah M.
The price is HK$995
HK$3,597 total
includes taxes & fees
15 Nov - 16 Nov
16. Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near WineriesNorthwest Santa Rosa
9.8 out of 10, Exceptional, (76 reviews)
"Our stay was very comfortable."
Kim R.
The price is HK$2,259
HK$4,595 total
includes taxes & fees
16 Nov - 17 Nov
17. Wine Country Getaway
Wine Country GetawayMirabel Heights
10.0 out of 10, Exceptional, (33 reviews)
"Great place, would stay again!"
Rachel S.
The price is HK$1,553
HK$4,210 total
includes taxes & fees
12 Nov - 13 Nov
18. Charming Dog-Friendly Home Near Regional Park
Charming Dog-Friendly Home Near Regional ParkSebastopol
10.0 out of 10, Exceptional, (35 reviews)
"Great place to stay"
Michelle D.
The price is HK$1,276
HK$2,952 total
includes taxes & fees
16 Nov - 17 Nov
19. Relaxing Vineyard View, Rooftop Deck & Game Room
Relaxing Vineyard View, Rooftop Deck & Game RoomSebastopol
10.0 out of 10, Exceptional, (32 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!"
Jeff D.
The price is HK$1,188
HK$3,730 total
includes taxes & fees
15 Nov - 16 Nov
20. Cozy Wine Country Guesthouse with Private Pool & Yard
Cozy Wine Country Guesthouse with Private Pool & YardSanta Rosa
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful stay!"
Adam C.
The price is HK$2,470
HK$2,667 total
includes taxes & fees
15 Nov - 16 Nov
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.
Learn more about Windsor
Sip your way through family-owned wineries like Sonoma-Cutrer and La Crema Estate, savouring the laid-back charm of this Wine Country gem. Hike along the Russian River or tee off at Windsor Golf Club before exploring the eclectic shops and summertime entertainment around the town green.
