Windsor Castle

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Windsor holiday rentals

Outdoor pool, a heated pool

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6
Windsor
The price is HK$1,567
HK$2,961 total
includes taxes & fees
30 Jun - 1 Jul
TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6
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, (45 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$1,567
HK$2,945 total
includes taxes & fees
29 Jun - 30 Jun
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Outdoor pool, a heated pool

One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6

One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6
Windsor
The price is HK$1,567
HK$2,961 total
includes taxes & fees
21 Jun - 22 Jun
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6
Outdoor pool, a heated pool

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
Windsor
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,567
HK$2,961 total
includes taxes & fees
21 Jun - 22 Jun
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
Pool

Eastside Eden - Pool, Hot Tub and Tastings Included

Eastside Eden - Pool, Hot Tub and Tastings Included
Healdsburg
9.0 out of 10, Wonderful, (4 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. "
United States
Dan M.
The price is HK$6,590
HK$12,830 total
includes taxes & fees
25 Jun - 26 Jun
Eastside Eden - Pool, Hot Tub and Tastings Included
Fridge, microwave, oven, stovetop

1 Block To St Helena Main Street Shops, Restaurants! Avail June 1-7!

1 Block To St Helena Main Street Shops, Restaurants! Avail June 1-7!
Downtown St. Helena
10.0 out of 10, Exceptional, (274 reviews)
"Great stay in a great location. The home was comfortable, had all the amenities for comfort, and was an easy walk into town. Scenic, quiet neighborhood. We would love to come back!"
United States
Margaret L.
The price is HK$9,403
HK$12,529 total
includes taxes & fees
22 Jun - 23 Jun
1 Block To St Helena Main Street Shops, Restaurants! Avail June 1-7!
Interior

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Downtown St. Helena
10.0 out of 10, Exceptional, (264 reviews)
"Amazing house, great location, hosts were very responsive. "
United States
Kevin C.
The price is HK$12,929
HK$16,647 total
includes taxes & fees
14 Jun - 15 Jun
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Towels

Downtown Cottage House

Downtown Cottage House
Downtown St. Helena
9.6 out of 10, Exceptional, (25 reviews)
"The location of the property is the best. "
United States
Kim B.
The price is HK$6,386
HK$9,687 total
includes taxes & fees
30 Jun - 1 Jul
Downtown Cottage House
Property grounds

Ambrose Bierce House

Ambrose Bierce House
Downtown St. Helena
9.8 out of 10, Exceptional, (29 reviews)
"The innkeepers were outstanding. The facility is wonderful - easy location to enjoy St. Helena and Napa Valley."
United States
Steve H.
Ambrose Bierce House
TV

Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Very homey comfortable place. Peaceful 😊"
United States
Carol
Emerald Lodge quiet efficiency
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$1,638
HK$1,826 total
includes taxes & fees
14 Jun - 15 Jun
Backyard Garden Oasis
Exterior

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.8 out of 10, Exceptional, (40 reviews)
"Host, amenities, location….all excellent. "
United States
Amy B.
The price is HK$2,343
HK$3,214 total
includes taxes & fees
15 Jun - 16 Jun
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Terrace/patio

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 reviews)
"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 traveller
The price is HK$2,108
HK$2,894 total
includes taxes & fees
15 Jun - 16 Jun
Escape to wine country in your independent cottage in downtown Calistoga
Outdoor dining

WineCountry Retreat + Casita,Bocce & Sunset Views!

WineCountry Retreat + Casita,Bocce & Sunset Views!
Glen Ellen
9.4 out of 10, Exceptional, (15 reviews)
"The owner was easy to talk to and checked in daily if we had any issues or help needed. "
United States
Christopher L.
The price is HK$2,183
HK$5,725 total
includes taxes & fees
28 Jun - 29 Jun
WineCountry Retreat + Casita,Bocce & Sunset Views!
Exterior

Luxury Napa Estate With Pool/Hot-tub/Concierge

Luxury Napa Estate With Pool/Hot-tub/Concierge
Calistoga
10.0 out of 10, Exceptional, (59 reviews)
"En suite rooms were perfect for group travel. The house was beautiful and comfortable. Hosts were very attentive and helpful. "
United States
Caylin E.
The price is HK$12,678
HK$20,380 total
includes taxes & fees
30 Jun - 1 Jul
Luxury Napa Estate With Pool/Hot-tub/Concierge
Dining

Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49 reviews)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
United States
Robert
The price is HK$1,403
HK$1,785 total
includes taxes & fees
14 Jun - 15 Jun
Comfort and Style in Our Queen Cottage
TV, fireplace, books

Napa Valley Retreat in Calistoga!

Napa Valley Retreat in Calistoga!
Calistoga
9.8 out of 10, Exceptional, (33 reviews)
"This cozy place was exactly as pictured and spotless. Communication with the owners was easy and responsive. We really enjoyed our stay and would happily return."
United States
Summer S.
The price is HK$2,970
HK$3,838 total
includes taxes & fees
23 Jun - 24 Jun
Napa Valley Retreat in Calistoga!
Outdoor dining

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.4 out of 10, Exceptional, (27 reviews)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
The price is HK$571
HK$1,405 total
includes taxes & fees
17 Jun - 18 Jun
Cobb Mountain Chalet King Size Suite
Living area

Rouge Cobb Mountain Hotel - Cabin 1

Rouge Cobb Mountain Hotel - Cabin 1
2.0 star property
Cobb
10.0 out of 10, Exceptional, (1 review)
"Quaint mountain cabin, relaxing, clean, pet friendly, easy check in"
United States
Bethany
The price is HK$1,033
HK$2,098 total
includes taxes & fees
15 Jun - 16 Jun
Rouge Cobb Mountain Hotel - Cabin 1
TV, fireplace, stereo

Sonoma Creek Haven - Creekside Hot Tub Retreat

Sonoma Creek Haven - Creekside Hot Tub Retreat
Kenwood
10.0 out of 10, Exceptional, (15 reviews)
"This place was amazing! Close to wineries, but private and felt like an escape! "
United States
Ellie R.
Sonoma Creek Haven - Creekside Hot Tub Retreat
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

DoubleTree by Hilton Sonoma - Wine Country

DoubleTree by Hilton Sonoma - Wine Country

8/10 Good
"Room was a little to hard for us"
Paul 1-night trip
Posted 2 hours ago
DoubleTree by Hilton Sonoma - Wine Country

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?

Bird Watcher Paradise 2 Bedroom 2 Bath with Beautiful View: This holiday home rental outside of Windsor is located on the waterfront, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Windsor?

Choose from 32 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.