Windsor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Windsor holiday rentals

A heated pool

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 HK$1,563
HK$2,914 total
includes taxes & fees
16 Feb - 17 Feb
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Dining

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 HK$2,603
HK$6,766 total
includes taxes & fees
18 Feb - 19 Feb
Elegant Vineyard Living at a Private Wine Country Estate
Exterior

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 HK$1,097
HK$2,398 total
includes taxes & fees
16 Feb - 17 Feb
Enchanting Retreat in the heart of Redwoods
TV, fireplace

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 HK$1,182
HK$2,501 total
includes taxes & fees
18 Feb - 19 Feb
Tranquil Redwood Retreat
Porch

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 HK$1,388
HK$1,548 total
includes taxes & fees
16 Feb - 17 Feb
Backyard Garden Oasis
Free WiFi

Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
The price is HK$749
HK$2,137 total
includes taxes & fees
15 Feb - 16 Feb
Sonoma Stonehouse, Wine Country Vibes
Interior

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
Guerneville
The price is HK$1,337
HK$3,374 total
includes taxes & fees
17 Feb - 18 Feb
Russian River Retreat! Woodsy Guerneville Bungalow
2 bedrooms, iron/ironing board, travel cot, free WiFi

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 HK$1,290
HK$3,212 total
includes taxes & fees
17 Feb - 18 Feb
Glen Ellen Retreat #3 King Beds
Exterior

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 HK$1,477
HK$3,683 total
includes taxes & fees
16 Feb - 17 Feb
Charming King Cottage
Outdoor dining

Rouge Cobb Mountain Hotel - Cabin 2

Rouge Cobb Mountain Hotel - Cabin 2
2.0 star property
Cobb
The price is HK$900
HK$1,905 total
includes taxes & fees
18 Feb - 19 Feb
Rouge Cobb Mountain Hotel - Cabin 2
Beach

The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (47 reviews)
"Great location to walk to town!"
United States
Brenda R.
The price is HK$766
HK$1,507 total
includes taxes & fees
18 Feb - 19 Feb
The Tiny Tipsy Turtle
Terrace/patio

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 HK$1,368
HK$3,308 total
includes taxes & fees
17 Feb - 18 Feb
Glen Ellen Retreat #1 Hot Tub and King Beds
TV

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 HK$758
HK$1,699 total
includes taxes & fees
17 Feb - 18 Feb
Emerald Lodge quiet efficiency
Fridge, microwave, oven, stovetop

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 HK$2,103
HK$4,426 total
includes taxes & fees
18 Feb - 19 Feb
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Exterior

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 HK$2,149
HK$2,952 total
includes taxes & fees
16 Feb - 17 Feb
Escape to Wine County in your independant Cottage in Downtown Calistoga
Outdoor pool

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 HK$907
HK$2,092 total
includes taxes & fees
1 Mar - 2 Mar
2 Hidden Wine Country Gem Upstairs Unit
Terrace/patio

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 HK$1,172
HK$2,101 total
includes taxes & fees
19 Feb - 20 Feb
Cozy cabin deep in the redwoods / WiFi & Hot Tub
Dining

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 HK$1,321
HK$3,476 total
includes taxes & fees
16 Feb - 17 Feb
Comfort and Style in Our Queen Cottage
Terrace/patio

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 HK$1,915
HK$3,753 total
includes taxes & fees
17 Feb - 18 Feb
Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown
Outdoor dining

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 HK$1,399
HK$3,751 total
includes taxes & fees
3 Mar - 4 Mar
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

10/10 Excellent
"The room was modern looking, tasteful, and roomy, and the bed was very comfortable with an assortment of pillows."
Nicki 1-night trip
Posted 2 days ago
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

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 holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Powell's Sweet Shoppe - Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 are some of the best holiday rentals that Windsor has to offer?

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH: This holiday home rental outside of Windsor is located by the ocean, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Windsor?

Choose from 29 Expedia holiday rentals in Windsor for a memorable holiday.

What can I see and do in Windsor?

Family-friendly attractions include Powell's Sweet Shoppe - Windsor and Dom Whitney Tasting Lounge, 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 holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.