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Windsor Vacation Rentals

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Check prices for these dates

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Windsor vacation rentals

Outdoor spa tub
Private Vineyard Estate | Sleeps 10

Private Vineyard Estate | Sleeps 10

Private Vineyard Estate | Sleeps 10
Windsor
9.6 out of 10, Exceptional, (4)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
The price is ￥101,205
￥193,503 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Private Vineyard Estate | Sleeps 10
Front of property
The Ranch at Lake Sonoma

The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
10.0 out of 10, Exceptional, (2)
"Nice camping spot "
United States
Evelyn
The price is ￥9,263
￥10,559 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Ranch at Lake Sonoma
Exterior
Enchanting Retreat in the heart of Redwoods

Enchanting Retreat in the heart of Redwoods

Enchanting Retreat in the heart of Redwoods
Guerneville
8.8 out of 10, Excellent, (12)
"Beautiful, clean house nestled in the woods. Loved the hot tub and the fire pit in the AM. Super comfortable mattresses."
United States
Jennifer H.
The price is ￥23,578
￥49,891 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Enchanting Retreat in the heart of Redwoods
Property grounds
Backyard Garden Oasis

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is ￥27,703
￥30,889 total
includes taxes & fees
Dec 29 - Dec 30
Backyard Garden Oasis
Meeting facility
Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.6 out of 10, Excellent, (27)
"Beautiful quiet retreat "
United States
Belwadi
The price is ￥25,122
￥28,011 total
includes taxes & fees
Dec 29 - Dec 30
Mandala Springs Wellness Retreat Center
Exterior detail
Cobb Mountain Chalet Main For

Cobb Mountain Chalet Main For

Cobb Mountain Chalet Main For
Cobb
9.6 out of 10, Exceptional, (14)
"A always a great stay this is my fourth stay."
United States
Richard D.
The price is ￥11,102
￥27,689 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Cobb Mountain Chalet Main For
Outdoor dining
The Tiny Tipsy Turtle

The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
2.0 star property
Guerneville
10.0 out of 10, Exceptional, (42)
"Great location to walk to town!"
United States
Brenda R.
The price is ￥15,282
￥30,059 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Tiny Tipsy Turtle
Property grounds
Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.0 out of 10, Wonderful, (2)
"This is a wonderful place to stay in Sebastopol. It is comfortable, cosy, quiet and well appointed - comparable to a suite in a nice hotel. There is good access, parking and a great location. Everything worked perfectly. The only issue is that entry to the room is via a spiral stair case that would be difficult for some people with disabilities. "
United States
Joe B.
The price is ￥21,286
￥38,655 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Sebastopol Lux Walk toTown Guest Suite
Outdoor dining
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
10.0 out of 10, Exceptional, (1)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
The price is ￥23,859
￥74,839 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Fridge, microwave, oven, stovetop
Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency
Middletown
10.0 out of 10, Exceptional, (1)
"Very homey comfortable place. Peaceful 😊"
United States
Carol
The price is ￥15,926
￥34,964 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Emerald Lodge quiet efficiency
Terrace/patio
Escape to Wine County in your independant Cottage in Downtown Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga
Calistoga
9.6 out of 10, Exceptional, (30)
"Great getaway for a couple"
United States
David G.
The price is ￥42,884
￥58,894 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Escape to Wine County in your independant Cottage in Downtown Calistoga
Outdoor dining
Glen Ellen Retreat #3 King Beds

Glen Ellen Retreat #3 King Beds

Glen Ellen Retreat #3 King Beds
Glen Ellen
10.0 out of 10, Exceptional, (70)
"We thoroughly enjoyed our stay! Very nice home - very clean, comfortable and just as advertised. Wonderful back yard to enjoy as well. Very close to Sonoma and convenient to many areas. We would highly recommend this home and would definitely stay here again! "
United States
Larry B.
The price is ￥28,069
￥66,243 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Glen Ellen Retreat #3 King Beds
Terrace/patio
Escape to Wine Country in your independant Cottage in Downtown Calistoga

Escape to Wine Country in your independant Cottage in Downtown Calistoga

Escape to Wine Country in your independant Cottage in Downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (2)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
United States
Ronny
The price is ￥42,884
￥58,271 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Terrace/patio
Charming Wine Country Getaway: Cozy Hot Tub, BBQ, & Mini Golf Fun

Charming Wine Country Getaway: Cozy Hot Tub, BBQ, & Mini Golf Fun

Charming Wine Country Getaway: Cozy Hot Tub, BBQ, & Mini Golf Fun
Southwest Santa Rosa
9.8 out of 10, Exceptional, (57)
"Great place to launch your stay in Santa Rosa."
United States
Deirdre F.
The price is ￥20,740
￥73,936 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Charming Wine Country Getaway: Cozy Hot Tub, BBQ, & Mini Golf Fun
Interior
Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
Guerneville
The price is ￥26,666
￥67,312 total
includes taxes & fees
Dec 28 - Dec 29
Russian River Retreat! Woodsy Guerneville Bungalow
Outdoor pool
2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (21)
"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 ￥27,929
￥54,185 total
includes taxes & fees
Dec 28 - Dec 29
2 Hidden Wine Country Gem Upstairs Unit
Outdoor dining
Winemaker's Delight: 3BD/3BA Russian River Valley

Winemaker's Delight: 3BD/3BA Russian River Valley

Winemaker's Delight: 3BD/3BA Russian River Valley
Northwest Santa Rosa
9.8 out of 10, Exceptional, (72)
"Comfortable beds and clean place. We enjoyed it"
United States
Amy F.
The price is ￥26,198
￥68,119 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Winemaker's Delight: 3BD/3BA Russian River Valley
Beach
Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (62)
"Tim and Caroline’s cottage was perfect for our two night stay. We loved how close it was to the shops and restaurants in downtown Santa Rosa. Definitely recommend."
United States
Adam R.
The price is ￥26,666
￥59,650 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Wine Country Cottage in downtown Santa Rosa, CA
Outdoor dining
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Forestville
10.0 out of 10, Exceptional, (11)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
United States
Paul H.
The price is ￥31,188
￥77,128 total
includes taxes & fees
Jan 15 - Jan 16, 2026
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Terrace/patio
Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (3)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
United States
Anonymous traveler
The price is ￥42,884
￥58,894 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Escape to wine country in your independent cottage in downtown Calistoga
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

Oxford Suites Sonoma County

Oxford Suites Sonoma County

10/10 Excellent
"Very clean and mice staff"
LJ 1-night trip
Posted 22 hours ago
Oxford Suites Sonoma County

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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 wineries and top-notch restaurants. 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?

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH: Visitors like this Windsor vacation home rental. It is located by the ocean and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Windsor?

Choose from 29 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 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.