Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Windsor
9.2 out of 10, Wonderful, (44 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
The price is CA $271
CA $509 total
includes taxes & fees
Mar 1 - Mar 2
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

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)
"Stayed here for a wedding "
United States
Lanna E.
The price is CA $452
CA $1,189 total
includes taxes & fees
Feb 18 - Feb 19
Elegant Vineyard Living at a Private Wine Country Estate

Enchanting Retreat in the heart of Redwoods

Enchanting Retreat in the heart of Redwoods
Guerneville
8.8 out of 10, Excellent, (12 reviews)
"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 CA $191
CA $419 total
includes taxes & fees
Feb 16 - Feb 17
Enchanting Retreat in the heart of Redwoods

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (10 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is CA $205
CA $438 total
includes taxes & fees
Feb 16 - Feb 17
Tranquil Redwood Retreat

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51 reviews)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is CA $241
CA $269 total
includes taxes & fees
Feb 13 - Feb 14
Backyard Garden Oasis

Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
The price is CA $136
CA $380 total
includes taxes & fees
Feb 18 - Feb 19
Sonoma Stonehouse, Wine Country Vibes

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
Guerneville
The price is CA $232
CA $586 total
includes taxes & fees
Feb 13 - Feb 14
Russian River Retreat! Woodsy Guerneville Bungalow

Glen Ellen Retreat #3 King Beds

Glen Ellen Retreat #3 King Beds
Glen Ellen
10.0 out of 10, Exceptional, (73 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
The price is CA $224
CA $558 total
includes taxes & fees
Feb 16 - Feb 17
Glen Ellen Retreat #3 King Beds

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
The price is CA $256
CA $639 total
includes taxes & fees
Mar 3 - Mar 4
Charming King Cottage

Rouge Cobb Mountain Hotel - Cabin 2

Rouge Cobb Mountain Hotel - Cabin 2
2.0 star property
Cobb
The price is CA $153
CA $327 total
includes taxes & fees
Feb 18 - Feb 19
Rouge Cobb Mountain Hotel - Cabin 2

The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (46 reviews)
"Great location to walk to town!"
United States
Brenda R.
The price is CA $133
CA $263 total
includes taxes & fees
Feb 18 - Feb 19
The Tiny Tipsy Turtle

Glen Ellen Retreat #1 Hot Tub and King Beds

Glen Ellen Retreat #1 Hot Tub and King Beds
Glen Ellen
10.0 out of 10, Exceptional, (82 reviews)
"Very clean and excellent location."
United States
carrie k.
The price is CA $238
CA $575 total
includes taxes & fees
Feb 16 - Feb 17
Glen Ellen Retreat #1 Hot Tub and King Beds

Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Very homey comfortable place. Peaceful 😊"
United States
Carol
The price is CA $129
CA $296 total
includes taxes & fees
Feb 13 - Feb 14
Emerald Lodge quiet efficiency

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Dillon Beach
10.0 out of 10, Exceptional, (64 reviews)
"This cottage was so cute! So close to the beach, super comfortable beds, and Valerie was an awesome host! This is a must stay if you are looking for a place in Dillon beach "
United States
Lauren S.
The price is CA $365
CA $774 total
includes taxes & fees
Feb 18 - Feb 19
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

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, (33 reviews)
"Great getaway for a couple"
United States
David G.
The price is CA $373
CA $513 total
includes taxes & fees
Feb 16 - Feb 17
Escape to Wine County in your independant Cottage in Downtown Calistoga

2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (22 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 $158
CA $366 total
includes taxes & fees
Mar 5 - Mar 6
2 Hidden Wine Country Gem Upstairs Unit

Cozy cabin deep in the redwoods / WiFi & Hot Tub

Cozy cabin deep in the redwoods / WiFi & Hot Tub
Guerneville
10.0 out of 10, Exceptional, (1 review)
"We stayed the weekend with friends at this beautiful hideaway in the woods and had a wonderful time. The house was spotless, the jacuzzi was perfect, the lighting was fun and ethereal, the fireplace was cozy, tv was easy to operate and had Netflix (thanks!). The beds are on the soft side, and curtains are sheer, which didn’t bother us, but that might be hard for some folks. We had a great time! Thank you so much!!!"
United States
Laine & Guy H.
The price is CA $204
CA $368 total
includes taxes & fees
Feb 19 - Feb 20
Cozy cabin deep in the redwoods / WiFi & Hot Tub

Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49 reviews)
"The cottage was very well appointed, very clean and comfortable. we really enjoyed our 2 night stay!Communication, check in and out were a breeze!Thank you!!"
United States
Kevin T.
The price is CA $229
CA $603 total
includes taxes & fees
Mar 2 - Mar 3
Comfort and Style in Our Queen Cottage

Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown

Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown
Guerneville
10.0 out of 10, Exceptional, (45 reviews)
"Great location, very clean, private hot tub, bed was comfortable. "
United States
Peter J.
The price is CA $333
CA $657 total
includes taxes & fees
Feb 17 - Feb 18
Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown

Bright and modern - Water views - Close to beach

Bright and modern - Water views - Close to beach
Dillon Beach
10.0 out of 10, Exceptional, (18 reviews)
"We had a blast perfectly located next to store and beach and an absolutely beautiful home!"
United States
Donald H.
The price is CA $257
CA $674 total
includes taxes & fees
Mar 3 - Mar 4
Bright and modern - Water views - Close to beach
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 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?

Bodega Bay on the Edge of Pacific Ocean: 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. Make the most of the garden in this rental home to help you unwind.

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 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.